Everyday Carry With J Fig

On this edition of EDC, Ashley sat down with JFig, aka @rule_of_thumbs, to discuss his go-to EDC items. Here’s a peek at what he carries in his bag to ensure a successful day.

Thanks to Jose for joining us for this video and thanks to IWC, one of our favorite watch brands of all time, for helping make this video happen!

Featured Items

Backpack

Computer

Journal

Dopp Kit

Pomade

Eye Balm

Lip Balm

Sunglasses 1

Sunglasses 2

Sunglasses 3

Headphones

Camera

Iphone

Phone case

Apps:

VSCO

Snapseed

Venmo

Spotify

Wordscapes

Follow J Fig

Instagram

Men’s Denim/Jean Jackets & How To Wear Them

After I released my Top 5 Fall Essentials article/video, I received a lot of questions about how to style different washes of denim jackets. I heard you loud and clear, so here’s some of my favorite ways to style them.

Light Wash

To avoid looking like you’re wearing a Canadian tuxedo, wear light wash denim jackets with chinos. You can pretty much get away with any color, but my favorites are navy, green, brown, and burgundy. My classic go-to formula is a t-shirt, chinos, and chukka boots. Crewneck sweaters or oxford button-downs are also good options as well.

$230 – Allsaints denim jacket – One of my favorite denim jackets currently available. I love the lighter wash and distressed touches and the slim fit is incredibly flattering, which is really hard to find in denim jackets. It fits true to size.
$20 – Topman striped t-shirt
$68 – J.Crew slim-fit stretch chino pant in green and brown (click here for their straight leg chinos)
$128 – Brooks Brothers suede belt in brown
$295 – Allen Edmonds plain-toe chukka boots
$318 – John Varvatos sunglasses
$5 – Perlon Watch Strap

Alternate Denim Jacket 

$90 – Levi’s denim jacket (in Queen) – You can never go wrong with this iconic denim jacket. Go with the next size down for this one because it’s not as fitted as the AllSaints one above and you always want a snug fit in the arms and body for all your denim jackets.

Dark Wash

If you only have the budget for one denim jacket, a dark washed one is what I’d choose. I love how dark the wash is because it’s easier to dress it up or down and it also has a slimming effect. I would avoid wearing jeans with a dark wash jacket unless they’re black because I don’t think it looks great and typically most men don’t know how to pair different washes of denim well. You can never go wrong with a pair of chinos and a crewneck t-shirt or sweater. If you want to dress the jacket up more, than pair it with some wool trousers and a collared shirt like I did in my fall accessory essentials article/video.

$118 – J.Crew denim jacket – Definitely go a size down than normal because you want a snug fit. Otherwise, the fit will be boxy which looks unflattering on every man regardless of your body type.
$24 – J.Crew t-shirt
$225 – J.Crew striped sweater
$40 – Uniqlo chinos in navy
$179 – Johnston & Murphy chukka boots
$415 – Tom Ford sunglasses 52mm

Alternate Denim Jacket 

$90 – Levi’s denim jacket (in Rinse) – Go with the next size down because you want a snug fit.

Grey Or Black Wash

Tall, dark, and handsome is how I describe the outfit you’ll be wearing with a grey (or black) denim jacket. Keep it all black – t-shirt, jeans, and boots. You can also go with a white t-shirt but I love how sharp an all black outfit looks with a gray denim jacket adding that perfect pop of monochrome color – it’s especially perfect for a night out.

$285 – AllSaints denim jacket
$75 – AllSaints black t-shirt
$168 – Diesel jeans
$750 – Prada chelsea boots
$415 – Tom Ford sunglasses in black

Alternate Denim Jacket 

$98 – Levis denim jacket

Top 10 Men’s Spring Essentials

There’s only a few weeks of Winter left, so pretty soon we’re all going to have to start thinking about transitioning to our Spring wardrobe. So in addition to your year-round Men’s Essential staples that are already in your closet, Jordan O’Brien from The Gentlemans Cove and I each came up with a list of 10 Spring Essentials that every man should own.

 

 

My Top 10 Men’s Spring Essentials

1. Lightweight, Spring Suit

Whether you go with a linen, cotton, seersucker, or lightweight wool suit, these options will make a statement and keep you cool throughout the Spring and Summer months.

Lightweight Suit Ashley Weston

$650 – J. Crew Ludlow Geyser Grey Italian Wool Suit
$500 – Brooks Brothers Red Fleece Navy Windowpane Suit 
$300 – TopMan Dark Brown / Burgundy Suit 
$105 – H&M Dark Green Cotton Stretch Suit

2. Linen or Lightweight Blazer

These lightweight blazers are perfect for casual Fridays at work or heading to lunch or dinner with friends. They’re a great way to insert a stylish statement while keeping cool. Linen will wrinkle a bit, but that’s part of its character so embrace it.

Lightweight Blazer Ashley Weston 1

$400 – Suitsupply Havana Green Check Sportcoat
$358 – Brooks Brothers Windowpane Linen Sportcoat
$168 – J.Crew Unstructured Ludlow Cotton-Linen Blazer
$99 – H&M Linen-Blend Navy Blazer  

3. Gingham Button Up Shirt

I love gingham shirts for the Spring because they can be worn dressed up with a suit or blazer or dressed down on their own or underneath a sweater. I included some great lavender, navy, and light grey gingham options below.

Gingham Button Up Ashley Weston

$450 – Ralph Lauren Purple Label Aston Gingham Dress Shirt 
$88 – J.Crew Ludlow Navy Gingham Shirt
$80 – Banana Republic Grant Fit Silver Gingham Shirt
$55 – The Tie Bar Grey Gingham Shirt

4. Silk Knit Tie

There’s no other brand that I love more than The Tie Bar. The quality, construction, and color/pattern choice can’t be beat by any other brand. Like I’ve always said, they’re not paying me to say this.

Silk Knit Tie Ashley Weston

$25 – The Tie Bar Scramble Knit Blue Polkas
$25 – The Tie Bar Knit Strip Brown
$25 – The Tie Bar Knitted Wine
$25 – The Tie Bar Midnight Navy

5. Polo Shirt

Polo shirts instantly make an outfit look more put together and Spring is the perfect time to start wearing them. I like John Varvatos, but be careful if you’re not in shape or have erect nipples because their silkier shirts will highlight these areas. The fit on Theory and Fred Perry polos is excellent and H&M is my go-to when I’m more price-conscious. You’ll need to replace those roughly every 8 weeks though due to fading.

Polo-Shirt-Ashley-Weston-Mens-Clothing-Fit-Guide $198 – John Varvatos Collection ‘Hampton’ Silk & Cotton Polo Shirt
$95 – Theory Cotton Polo
$85 – Fred Perry Navy/White Tipped Polo Shirt
$13 – H&M Polo Shirts

6. Short Sleeve Button Up Shirt

Not only do short sleeve button-up shirts look stylish, but every man (regardless of age or body type) can wear these. There’s currently so many great options from J.Crew and come March/April, Topman will have an equally great selection.

Short Sleeve Button Up Ashley Weston $480 – Prada Slim Fit Star Print Cotton Poplin Shirt
$128 – Todd Snyder Short Sleeve Floral Print Shirt
$60 – J.Crew Short-Sleeve Shirt in Jungle Print
$60 – J.Crew Short-Sleeve Oxford Shirt in Blue
$60 – J. Crew Short-Sleeve Shirt in Striped Heather Poplin 
$55 – TopMan Blue Abstract Print Short Sleeve Casual Shirt

7. Suede Bomber Jacket

I’ve maintained in some of my other videos and articles that you should save your suede for Spring. Well, it’s time to break out those items. I love the options below – you can choose from navy, light grey, and brown suede jackets. The A.P.C. jacket is a BIFL piece and will never go out of style.

Suede Bomber Jacket Ashley Weston$1,455- A.P.C. Louis W Suede Bomber Jacket
$1,085 – Hackett Mayfair Suede Bomber Jacket
$160 – TopMan Light Grey Faux Suede Formal Bomber Jacket
$160 – TopMan Faux Suede Formal Bomber Jacket

8. Penny Loafers

Finally we’re entering ankle season, which means penny loafers can finally be worn. I love Ferragamo’s loafers (I got a pair for my fiance Dorian 2 or 3 years ago) and they’re totally worth the price because they definitely hold up and still look great after years and years of wear.

Ferragamo Penny Loafer 2 Ashley Weston$760 – Ferragamo Penny Loafer Shoe
$195 – Jack Erwin Archie Penny Loafer Hazelnut
$185 – Johnston & Murphy Stratton Penny

9. Suede Monkstraps

Suede monkstraps, whether you get a dark brown, grey, or navy pair, can just take an outfit to another level. It’s such a stylish touch to any outfit and can be worn with a suit, chinos, or jeans. Make sure to Scotch Guard them before you wear them for the first time – always gotta protect your suede items!

BB Suede Monk Straps Ashley Weston$698 – Brooks Brothers Navy Suede Double Monk Strap
$398 – Brooks Brothers Suede Double Monk Strap Shoes
$275 – Crosby Square Conley Double Monk Strap Shoe (Espresso and Navy)
$80 – H&M Suede Monkstrap Shoes

10. Chinos

Chinos should only be worn in Spring, Summer, and early Fall and that’s it. They’re a great alternative for those days when you don’t feel like wearing jeans and when you want to just feel cool and comfortable.

Chinos Ashley Weston$575 – Maison Margiela Cotton-Twill Chinos
$75 – J.Crew Broken-In Chino in 484 Fit
$30 – Uniqlo Slim Fit Chinos
$30 – H&M Chinos Skinny Fit

Jordan’s 10 Men’s Spring Essentials

1. Huaraches

These as well as other great alternatives were included in my Summer Essentials E-Book. A lot of Jordan’s picks I actually included in that e-book so be sure to check it out if you haven’t already 🙂

Huaraches Ashley Weston $165 – Vintage Artisan Classico Brown
$88 – Chamula D.F. Dk. (Brown or Navy)
$88 – Chamula Cancun with Natural Crepe Sole

2. Linen Suit

Linen, as well as the other lightweight fabrics I also included in my list, is very breathable and will keep you cool during the warmer months. Here are some of my favorite items currently available.

Linen Suit Ashley Weston$2,000 – Burberry Slim Fit Wool Silk Linen Three-Piece Part-Canvas Suit
$349 – Brooks Brothers Milano Fit Check Linen Suit
$99 – H&M Linen-Blend Suit Jacket
$50 – H&M Linen-Blend Suit Pant 

3. Panama Hat / Straw Fedora

Whether you need some extra sun protection or want to look stylish while staying cool, straw hats are super breathable and lightweight. Every year I get J.Crew’s panama hat, but it only lasts the season before it starts to fall apart. I’m currently eyeing Loro Piana, Brooks Brothers and Stetson’s hats because I know I can count on the quality and construction.

Panama Hat Ashley Weston 1$735 – Loro Piana Laurence Straw Panama Hat
$298 – Brooks Brothers Straw Fedora
$287 – Lock and Co Napoli Hat
$105 – Stetson Men’s Centerdent Fine Panama Hat
$65 – J. Crew Paulmann panama hat with striped band

4. Basic Striped T-Shirt

Striped t-shirts are super easy to insert into your current wardrobe. They look great with your suits, blazers, bomber jackets or just on their own.

Stripe Tshirt Ashley Weston$90 – Todd Snyder Slim-Fit Striped Cotton T-Shirt
$88 – Todd Snyder Fine Stripe Button Pocket T-Shirt in Maroon
$60 – J. Crew Wallace & Barnes Indigo T-Shirt in Stripe
$45 – J. Crew Garment-Dyted T-Shirt in Microstripe
$35 – TopMan Selected Homme Navy and Off White Stripe T-Shirt

5. Long Sleeve Henley Shirt

I like long sleeve henleys when they’re worn as a layering piece, so underneath a casual button down shirt paired with some dark wash jeans and boots or sneakers. If you’re a slim or wider gentleman, I highly advise against wearing henleys on their own because they emphasize your body size even more (and not in a good way).

Long Sleeve Henley Shirt Ashley Weston$150 – Rag & Bone Slim-Fit Mélange Cotton-Blend Jersey Henley T-Shirt
$59 – L.L. Bean Signature Slub Henley
$39.50 – J.Crew Slim Broken-In Henley

6. Denim Jacket

If you’re new to wearing denim jackets, I suggest going with a black or dark grey version because it’ll be a lot easier to wear, especially if you wear jeans a lot because you don’t want to look like you’re wearing a Canadian tuxedo.

Denim Jacket Ashley Weston$295 – Rag & Bone Standard Issue Washed-Denim Jacket
$195 – All Saints Mens Hockett Denim Jacket
$90 – Levi’s The Trucker Jacket (in rinse or lamar black stretch)
$40 – H&M Denim Jacket

7. Lightweight Jacket

On those windy or rainy days, having a lightweight jacket that can combat the elements while looking stylish is always what I strive to find.

Casual Jacket Ashley Weston$280 – Saturdays Travis Windbreaker (Sage or Clay)
$200 – J. Crew Field Mechanic Jacket
$160 – Under Armour Sportswear Meters Panelled Shell Hooded Jacket
$40 – Uniqlo Lightweight Packable Hooded Jacket

8. White Sneakers

I have a whole video and article dedicated to white sneakers because I truly believe every man, regardless of age or body type, should own a pair.

White-Sneakers-Ashley-Weston-Mens-Wardrobe-EssentialsHeader$100 – Nike Tennis Classic Ultra
$75 – Adidas Originals Stan Smith Sneaker
$65 – Converse ‘Jack Purcell’ Classic Low Top Sneaker

9. Classic Timeless Pair of Sunglasses

Be sure to check out my Sunglasses story for specific options I recommend based on your face shape.

Rayban Wayfarer Ashley Weston$325 – Oliver Peoples L.A. Coen Sun
$140 – Ray Ban RB2132 58 New Wayfarer
$95 – Warby Parker Barkley Sunglasses
$95 – Warby Parker Beckett Sunglasses

10. NATO Strap

Interchanging your watch straps is an easy way to insert some fun and personality into your outfit.

NATO Strap Watches Ashley Weston

Here’s a great place for straps that I love – these are my favorite for Spring:
$8 – Navy Perlon Nato Strap
$8 – Navy and Grey Nato Strap
$8 – Dark Brown Perlon Strap
$8 – Grey Perlon Strap
$9 – Black, Red, And Green “JAMES BOND” PVD Nato Strap

As far as watches go, see my Watch article/video.

Fall and Winter Boots For Men

There’s 3 types of Fall and Winter Boots for men that I love for this time of year – Dress, casual and chukka boots.

The reason I love boots for Fall/Winter is that they go so well with jeans, wool trousers and fall/winter suits. They also do a great job of keeping your feet warm and protected from the elements – while looking classy and more refined than a pair of hiking boots or something that’s just a straight utility item.

Now, if you live in an area with a good amount of snow or rain, then you should probably have specialty boots for the crazy days, too, but those are outside the scope of this article. 

The difference between dress and casual boots

Dress boots are more formal and can be worn with a suit or wool trousers. They have a sleeker profile, usually leather or dainite soles, and are made out of shinier calf skin, as opposed to cow hide. Dress boots are like dress shoes with a shaft, basically.

Casual boots usually have more room in the toe box, the leather is usually a thicker cowhide that is more matte, and the soles usually have lugs on them. They look a little less dressy and sophisticated, which is why they look so great with jeans, but you can also still wear them with wool trousers.

My Requirements for a good Fall/Winter Boot

These items apply to all the types of boots – dress, casual and chukka boots:

1. A slim profile and not chunky

Timberlands (right) are the exact opposite of what I’m looking for in a good boot. You want a nice, rounded toe box with a slim profile as well as sole like the image below.

dressvsworkbootashleywestoncropped

2. Plain, Cap Toe or Broguing

I like all 3 of them, but just like with my dress shoes, I’ll always prefer a plain or cap-toe, but broguing is also acceptable. Broguing is not really my preference because I think a lot of guys overdo it with the broguing, burnished toes, etc. Too much can easily look gaudy if you’ve got too much going on in your outfit.

plaincaptoebroguingashleyweston

3. Lugged, Dainite or Rubber soles

These will give great grip in any type of weather. A normal dress boot has smooth leather on the bottom and you will slip and slide like crazy in wet weather. If you’re not in a climate with rain/snow, then you can go with straight leather bottoms typically found on most dress boots, but I see no reason to do that when any rubber bottom aside from lugged will look very similar with the extra benefit of additional traction.

mensleatherbootsolesashleyweston

4. Be brown or black leather

Go with nice dark chocolate or walnut brown first, then get black if you don’t have them already. Brown is a great fall/winter color and is easier to wear with casual AND more formal outfits. But be careful about getting a really specific brown color, like oxblood. As I’ve said in my other shoe videos, it’s a great color but doesn’t compliment a lot of outfits, so get that color once you’ve got these basics down.

And please, whatever you do, don’t get those terrible boots that are already worn in. It’s much better for you to wear them in yourself and really personalize their look to your actual lifestyle.

5. NOT be Suede

For Fall and Winter boots, suede is the last material you should consider, unless you live in a dry climate like Southern California where it rains maybe 3 or 4 times a year. Otherwise, they’ll get screwed up very quickly with any amount of rain or snow. I don’t care how much scotch guard you use, nothing can stand up to that much abuse. So save the suede shoes for spring, please.

Can I wear boots with a suit?

Yes, but only when these 2 conditions are met:

  1. You’re wearing a heavier wool or tweed suit.
    For a visually heavy item like boots, you should understand fabric weights and pairing them with similar items. Even straight up dress boots can look odd with lighter weight wool suits. Make sure the wool is atlas 12oz thick. The easiest way to tell what a heavy wool suit feels like in person, is it should be as thick as a wool sweater (not as soft, though!)
  2. Your pants are hemmed to have no break.
    The hem of your pants will look sloppy and bunched at the ankle, otherwise. You can technically cuff the hem of your suit pants to do this, but if they’re super long, it’ll never look quite right. So I usually just get the pants hemmed to no break for this. But that means you can’t wear this suit with anything but boots now…unless you have your tailor let out the hem when the seasons change.

How To Tie Your Boots

Check out my shoe and boot tying video for how to tie your shoelaces properly.

Best Ways To Wear Boots For Men

fallwinteressentialsbootsashleywestonoutfit1

Topman Black Cotton Bomber Jacket 
TopMan Ribbed Turtle Neck Slim Fit
Rolex Oyster Perpetual Submariner Date
Tom Ford Black Snowdon Sunglasses
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Dress Belt

fallwinteressentialsbootsashleywestonoutfit2

Parajumpers Anthracite Urban Genesee Jacket
Brooks Brothers Milano Fit Button-Down Collar Dress Shirt
Rolex Oyster Perpetual Submariner Date
Tom Ford Black Snowdon Sunglasses
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Dress Belt

fallwinteressentialsbootsashleywestonoutfit3

Topman Faux Suede Flight Jacket (It’s technically a Peuterey jacket, but it’s only available in Europe)
Brooks Brothers Milano Fit Spread Collar Dress Shirt
IWC Portuguese Automatic Watch
Tom Ford Black Snowdon Sunglasses
H&M Black Melange Wool Suit Pants
Allen Edmonds Decatur Ave Dress Belt

The Best Fall Winter Boots For Men

Casual Boots

Budget Friendly

Aldo Acerrassi

$200 – Aldo Acerrassi

$175 – Aldo Etausen Boot (2 colors)
$175 – Johnston & Murphy Conard Wingtip Boot (3 colors)
$220 – Jack Erwin Carter Wingtip Boot (2 colors)

Designer

$350 – Allen Edmonds Long Branch Wingtip Boots


$318 – FRYE Tyler Lace Up (2 colors)
$395 – Wolverine 1000 Mile Boot 
$725 – Crockett & Jones Coniston Tan Boot
$775 – Crockett & Jones Islay Wingtip Boot

Dress Boots

Budget Friendly

Calvin Klein Darsey Brown Boot

$140 – Calvin Klein Darsey Dark Brown Leather Boots

$60 – Stafford Deacon Wingtip Leather Boots (2 Colors)
$135 – Stacy Adams Madison Boot (2 colors)
$140 – Calvin Klein Darsey Black Leather Boot

Designer

Allen Edmonds First Avenue Black Boot

$995 – Saint Laurent Polished Leather 

$645 – O’Keefe Algy Split-Toe Weatherproof Pebble-Grain Leather Boots
$748 – Brooks Brothers Peal & Co. Leather Wingtip Boots
$1,098 – Brooks Brothers Peal & Co. Cordovan Boots

Chukka Boots

Budget Friendly

Johnston & Murphy Fulton Chukka Black

$140 – Johnston & Murphy Fulton Black Chukka

$130 – Clark’s Desert Boot in Brown Suede
$75 – Aldo Granges Chukka Boot
$175 –Johnston & Murphy Conard Cap Toe Chukka (2 colors)
$198 – Johnston & Murphy Fulton Brown Chukka
$225 – Vince Camuto Branx Two-Eye Chukka (2 colors)

Designer

Allen Edmonds Dundee 2.0 Chocolate

 

$250 – Allen Edmonds Dundee 2.0 Suede Boots (2 colors)
$378 – FRYE Weston Chukka (3 colors)
$1,500 – John Lobb Elmer Chukka

 

That’s it! I hope you liked the article. Please share it via one of the buttons below if you did. 🙂

Sunglasses

So we’ve already established (in the series intro video) that the details in your wardrobe & appearance matter, and just like I talked about before, the first thing someone looks at is your face, so the things that sit ON your face, like sunglasses, should add to the overall sharpness of your outfit/appearance, not detract from it.

How many sunglasses should I own?

I’ve been asked this quite a few times and I think you should own 2-3 pairs. This will ensure your sunglasses will look appropriate with whatever outfit you’re wearing – no matter what. While you can use just 1 pair, I would recommend at least two to be safe.

Do I need to match sunglasses to my outfit?

You don’t technically need to match them to your outfit, but there’s an argument to be made for it, which I’ll get into in the next section.

What color sunglasses should I have?

In order to cover you for all outfits and seasons, you should own a black pair and tortoise shell pair. If you want crazier colors then you should definitely get them, but only AFTER you’ve got the basics covered.

Black

You want a black pair because they go very well with more formal outfits and/or they match with your black accessories – i.e. your shoes or watch strap. To me, it’s not ideal if you’re wearing brown accessories – shoes, watch strap, etc, and then throw on a pair of black sunglasses, but it is still perfectly acceptable because it’s far enough away from these other accessories that it won’t ruin the cohesion of the look. If you only have 1 pair of sunglasses, you should go with black because it goes with any outfit you could be wearing.

Brown/Tortoise shell

This color goes very well with casual outfits, but also looks fantastic with a navy suit and brown accessories. Again, you can get away with black sunglasses with a navy suit, but it’s not ideal.

Any Other Color

If you want to have a crazy fun pair, then go nuts here, but just don’t wear it with anything but casual outfits, otherwise you could start look like Bruce Vilanch. Again, a well-dressed man shouldn’t have anything standing out in an outfit, he needs everything to work in perfect harmony to create an amazing whole. This absolutely applies to sunglasses.

Aviators – The Exception

If your face shape allows you to wear Aviators and you want to wear those, always go with a silver/charcoal metal frame and black/grey/green lenses as the default or “black” option, like I talked about above. For your “brown” pair of sunglasses, go with a gold metal frame and brown lenses. You don’t want a black or brown frame because it looks cheesy and deviates too far away the timeless look of Aviators.


What Color Lenses should I have?

This one is simple and the default lenses are usually great, but here’s my preferences:

  1. Gradient – They look amazing and just give the sunglasses a nice, little extra touch of class.
    TomFordSnowdonSunglassesGradientLensesAshleyWeston
  2. Standard shaded/polarized – Most glasses will come with this type of lens that will probably match the color of the frame (black = black lenses, brown = brown lenses, etc.) and it’s perfectly acceptable, but if given the choice, I’d go with a gradient lens every time.
    Warby Parker Madison in Whiskey

Anything outside of these lens colors and types, included mirrored lenses, are a no go. They’ll detract from the polished look of your outfit and this is to be avoided because your accessories should never overshadow anything else you’re wearing.

Don't be like this guy.

Don’t be this guy.

The best sunglasses for your face shape

The type of sunglasses you should own is dependent on you face shape. You generally want the shape of your sunglasses to be the opposite of your face shape, so they’ll help provide balance to your facial features.

A quick note about the below chart, including other resources out there – most of them will be talking about as many as 10 different face shapes and trust me, it’s a waste of time. There’s really only 3 face shapes that every man falls into:

  1. Round
  2. Oval
  3. Square

Everything else is just nit-picking to fill up space on a website or magazine. The one that drives me the craziest is heart-shaped – that’s just an oval face with a wider forehead. If you’re considered heart-shaped according to the charts below, then just go with my oval suggestions.

You’ll notice that, outside of Aviators, I’m not recommending any frame-less style sunglasses and that’s because I think they just don’t look that great and never put my clients in them.

As for how to determine your face shape, the best resources I’ve found are from good ol’ LensCrafters and FramesDirect:

How To Find Your Face Shape Sunglasses Glasses Men Man Ashley Weston

How To Find Your Face Shape Sunglasses Glasses Men Man Ashley Weston1


How To Find Your Face Shape Sunglasses Glasses Men Man Ashley Weston2

Round Face

Roundfaceshape

If you have a round shaped face, you want to avoid round frames and go for more square/rectangular frames (i.e. Wayfarer style) or teardrop frames like Aviators. These styles will help give your face some dimension and break up the roundness, which is a good thing!

A quick note about why I don’t recommend Ray-Ban’s classic Wayfarers: I hate the angle of the lenses on them. Yes, they’re classic, but that still doesn’t mean they’re good. Notice how the frames are resting on the cheeks in the below picture? It’s annoying as hell and just looks bad on everyone.

WayfarersSunglassesAngleAshleyWeston

Designer Options

Oliver Peoples Brodsky in Sandalwood + G-15 Polar Glass
Barton Perreira Hopper in Black 
Saint Laurent Aviators in Gold

Budget-Friendly Options

Warby Parker Winston in Jet Black
I love the classic, square shape of these sunglasses. For the price point, they don’t feel cheap or heavy.
J. Crew Irving in Soft Tortoise
J. Crew Jack in Gold

Oval Face

Ovalfaceshape

For this face shape, you’re lucky, because you have the most choices for sunglasses. You can wear round, square/rectangular, or rounded square-shaped sunglasses. The one thing you want to do is make sure the frames are as wide as your face – this is very important! Otherwise, it’ll look like you’re wearing kid sunglasses. Also, don’t you ever wear teardrop frames, like what most aviators have, because it’ll also make your face appear long or droopy.

Designer Options

Tom Ford Snowdon in Shiny Black
Fun Fact: Daniel Craig wore these in Spectre. If you have a round or oval face, these Tom Ford sunglasses are one of my all-time favorites! Everything about these square frames – the color, timeless design, and overall weight – couldn’t be better. Also, they’re the perfect width for oval faces which is very important because they’ll look disproportionate if they’re not as wide as your face.
Tom Ford Snowdon Sunglasses in Havana
Oliver Peoples Masek Sunglasses in Matte Black + Grey Mineral Glass
Oliver Peoples Masek Sunglasses in Cocobolo + Cosmik Tone Glass
Think of these Oliver Peoples sunglasses as the rounder version of the Tom Ford frames.
John Varvatos Grand in Black 
John Varvatos Grand in Tortoise

Budget-Friendly Options

Topman Matte Black Sunglasses 
Warby Parker Downing in Jet Black 
Warby Parker Downing in Walnut Tortoise
The thinness of these plastic frames compliment its round shape and are great for men with oval or square faces. I also like that they kept the arms thin because some designers would go with wider arms which would make these frames look unbalanced. These aren’t as wide as the Tom Ford and Oliver Peoples frames that I recommend above, so if you do decide to try these out, then make sure they’re the proper width for your face.

Square Face

Squarefaceshape

For this face shape, you should look for round or teardrop frames. This will soften and balance your angular features. Avoid square or rectangle sunglasses because they’ll literally make you look like a block head

MinecraftBlockhead

Designer Options

Persol Sunglasses Suprema PO3007S in Black
Persol Sunglasses Suprema PO3007S In Tortoise
I love how sleek these frames are! The shiny finish and metal detailing on the arms adds to its sharp design. These are the perfect pair of sunglasses for men with square or oval faces.
Oliver Peoples Finley Esq. Sun in SMBK Moss Tortoise + Graphite
Oliver Peoples Finley Esq. Sun in Hickory Tortoise + Cosmik Tone Mineral Glass
Similar looking to the Persol sunglasses, the finish on both colors is matte and they’re slightly smaller in design.
Tom Ford Erin Aviator-Style Leather-Trimmed Gold-Tone Mirrored Sunglasses
Prada Aviator-Style Metal and Acetate Sunglasses

Budget-Friendly Options

Warby Parker Percey in Charcoal Fade
I LOVE the black to grey coloring of these frames. They look so expensive for what you’re paying for and I appreciate the simple, thin design which softens (in a good way!) the sharper features of a square-faced man. And they’re incredibly lightweight.
Warby Parker Madison in Whiskey
Ray-Ban Aviator at Collection in Gunmetal
Ray-Ban Aviator at Collection in Gold
Ray-Ban aviators are a timeless, iconic design that’s perfect for this face shape because it helps break up your angular features with the teardrop design.

Sunglasses Outfit Inspiration

(LOTS of inspiration images are also in my Summer Essentials Ebook)

Top 10 Men’s Summer Essentials – Bean Boozled Edition With Andrew Snavely from Primer Magazine

Andrew Snavely from PrimerMagazine.com joined me to compare our lists of the Top 10 Men’s Summer Essentials – with a disgusting twist.

If you don’t know the Bean Boozled Challenge, it’s a game where you have a 50/50 chance of getting a delicious jelly bean or one that’s flavored something like vomit, skunk, rotten eggs and a whole host of really vile flavors.

If our items didn’t match up, we had to spin the wheel of doom and see what flavors we got. I wish I could say this is the first time I’ve played this game, but unfortunately, I’ve had the pleasure of playing it before.

 

Straw Panama Hat

Nick Fouquet Straw Hat

Borsalino Straw Hat

J. Crew Paulmann Panama Hat with Indigo

Rag & Bone Sewn Straw Fedora

Rag & Bone Panama Hat

Zara Straw Hat

Brixton Pacific Fedora

Tortoise Shell Sunglasses

Tom Ford Snowdown

Tom Ford Frank

Ray Ban Clubmast Flash Lenses

Ray Ban Clubround

Persol Classic

John Varvatos Prince

John Varvatos Bond

Warby Parker Ames

Tote Bag

Frank Clegg Tall Tote

Jack Spade Canvas Tote 

Jack Spade Dipped Coal Bag

Saturdays NYC Reece Tote

Stanley & Sons Leather Tote

Herschel Tote Bag

Uri Minkoff Tote

Boat Shoes

Bottega Veneta Intrecciato Leather Boat Shoes

Sperry Top Sider Authentic 2 Eye

John Varvatos Schooner Boat Shoe

John Varvatos Star Boater Clip

Polo Shirt

Designer Options

John Varvatos Black Silk Cotton Hampton Polo

Sunspel Charcoal Jersey Polo Shirt

Tom Ford Navy Polo Shirt

Burberry Navy Silk Cotton Polo

Theory Black Boyd Polo

Budget-Friendly Options

H&M White Cotton Polo Shirt 

H&M Black Cotton Polo

Uniqlo Navy Dry Pique Short Sleeve Polo Shirt

J.Crew Black Pique Cotton Polo

Unlined Sport Coat

Brooks Brothers Seersucker Sport Coat

Brooks Brothers Herringbone Irish Linen Sport Coat

Givenchy Slim-fit Cotton-Blend Seersucker Blazer

J. Crew Ludlow Blazer in Italian Linen

J. Crew Ludlow Blazer in Italian Cotton

Loro Piana Ecru Woven Wool Silk & Linen Blend Blazer

Loro Piana Blue Toledo Slim-Fit Stretch-Cotton Blazer

Oliver Spencer Blue Theobald Slim-fit Linen & Cotton-blend Jacket

Saturdays x Mr. Porter Lumax Blazer

Theory Blue Rodolf Slim-fit Stretch-cotton Blazer 

Zara Linen Blazer

Swim Trunks

Everest Isles Daupner Short

Everest Isles Jacktar Trunk

Everest Isles Mayol Trunk

H&M Solid-Color Swim Short

Joe Fresh Men’s Board Short

Joe Fresh Men’s Board Short

Saturdays NYC Colin Boardshort

Saturdays NYC Danny Boardshort

Saturdays NYC Grant Offset Stripe Boardshort

Zara Basic Classic Swimsuit

Zara Basic Fashion Swimsuit

Chino Pants

Designer Options

Rag & Bone ‘Fit 2’ Slim Fit Khaki Chino

RRL Slim Fit Sand Chino

Tomas Maier Slim Fit Sand Chino

Brooks Brothers Red Fleece Navy Slim Fit Chino

Burberry Slim Fit Stretch Navy Chino

Rag & Bone ‘Fit 2’ Slim Fit Army Green Chino

Burberry Straight Fit Taupe Chino

Todd Snyder Navy Straight Fit Chino

Z Zegna Straight Fit Beige Chino

Budget-Friendly Options

Uniqlo Navy Men Slim Fit Chino

H&M Beige Chino Slim fit

JCrew Straight Fit ‘1040’ Navy Chino

Plain T-Shirts

A plain, short sleeved t-shirt is an essential because they’re super comfortable, timeless, and everyone wears them. Now whether you need a crew neck or v-neck t-shirt is dependent on a few factors that I’ll get into later on in this article.

If you’re like most of my clients, you’re probably wearing a t-shirt or polo shirt most of the time, so let’s make sure you look amazing in them. Before we get into that, though, I have a few bones to pick with men in regards to their t-shirts. They completely crap the bed in a few ways:

  1. Their shirts are full of logos.
  2. They don’t fit properly.
  3. The fabric is too thin, shiny, or worn out.
  4. A horrible combination of the above.

Types of T-Shirts For Men

A t-shirt is defined as:

A lightweight shirt without buttons, with short sleeves and no collar. Often made of cotton and frequently bears a picture or slogan.

Before we get into the finer points of t-shirts, let’s talk about the two different types, first. Before I started in the fashion industry, I didn’t know that there were only really two types of t-shirts. So let’s quickly get this out of the way.

Crew Neck

T-Shirts-V-Neck-Crew-Neck-Ashley-Weston-Mens-Wardrobe-Essentials-Ashley-Weston-Mens-Wardrobe-Essentials-2

These t-shirts have round collars that fit closely to the neck like the image above. You probably have these in your closet right now. They are great base items for layering or worn on their own. They work on most body types. See the below section about fit for more details.

V-Neck

T-Shirts-V-Neck-Crew-Neck-Ashley-Weston-Mens-Wardrobe-Essentials-Ashley-Weston-Mens-Wardrobe-Essentials

If your powers of deduction are strong, you’ll already know that the v-neck t-shirt is named as such because the neck is in the shape of a “v”. They also work on most body types. See the below section about fit for more details.

Long Sleeves

Long-sleeved shirts are not technially t-shirts. I put this here, because when I was first starting out, I swore that long-sleeved shirts, like Henleys, were also t-shirts. But, they’re not. Also, in my professional opinion you shouldn’t really own any long sleeve shirts. Henleys would be the only exception, but they only look good on certain body types. I’ll do an article about Henley shirts at a later time. But I don’t consider them a wardrobe essential.

If you need long sleeves, throw on a Oxford Button Down Dress Shirt, V-Neck Sweater Harrington Jacket or Blazer instead.

Logos & Designer T-Shirts

DesignerTShirt

I discussed my hatred of logos in my polo shirt article. And it definitely applies to t-shirts. Maybe more-so.

No self-respecting man should ever wear t-shirts with logos plastered all over them. We have enough billboards and advertisements in our lives, don’t turn your body into another one. Sports teams and concert/band tees are fine if worn to an event where it’s appropriate. But the worst is when I see guys wearing “designer” t-shirts. It just screams sucker, amateur and douche. Just don’t do it. If you own any of these, either throw them out right now orariGTFO

How T-Shirts Should Fit

See the T-Shirt Fit Guide for details. But I’ll quickly mention here, too, that no matter your age or body type, a t-shirt (any shirt, for that matter) should have a trim fit and lightly hug your body.

That doesn’t mean it should be skin tight, but it also doesn’t mean it should be baggy, either. A lot of my clients with larger builds tend to think that their shirts need to be baggy to hide their imperfections, but it actually works counter to that. It’ll highlight your imperfections if you attempt to hide them under larger swaths of fabric. And if you’re thinner, a larger shirt won’t add any bulk to your frame, it’ll just make you look even skinnier.

Fabric Choice

I can’t tell you how many nipples and belly buttons I see walking around town because guys are wearing undershirts or flimsy shirts with really thin or delicate fabrics as regular t-shirts.

Too Thin

I see a lot of guys wearing what looks like white undershirts because the fabric is so thin. I’ve honestly been searching for months for good white shirts that don’t show skin through. See my recommendations below.  Thin shirts/undershirts are not the same as regular t-shirts. Undershirts, true to their name, should only be worn underneath another shirt – usually an Oxford Button Down Dress Shirt or a Semi-Spread Collar Dress Shirt. They’re thin and soft because they’re purpose-built to go underneath something else.

Silky or Shiny appearance

The quickest way to look like a creepy uncle is to wear a shiny or silky t-shirt. You should only wear cotton and matte (not shiny) t-shirts. Nothing else.

Distressed or Worn out

Your t-shirts shouldn’t look like the garment equivalent of those terrible worn-out baseball caps. A t-shirt should look clean, comfortable and relatively new. Once they’ve got holes or they’re faded, even a little bit, they need to be replaced. Such is the nature of being a well-dressed gentleman. There’s nothing worse than old, stretched-out, or faded looking shirts, unless you’re deliberately going for that look.

You’ll get more usage out of your t-shirts if you wash in cold water and hang dry them. But once they’re stretched out or faded, it’s time to donate and replace them.

The Best T-Shirts For Men

Choosing the best t-shirts comes down to your body type, preference and the colors. I’ll reiterate again, because my older clients like to give me this excuse before they see the light: AGE DOESN’T FACTOR INTO WHAT SHIRTS YOU SHOULD GET – AT ALL.

Should I have V-Necks or Crew Necks?

Between the two, I would say it all depends on your preference. Some of my clients are adamant about their love or hate for one or the other. But if you don’t have a preference, I’d suggest getting one set of each. That way, you have the option to switch it up.

As for which ones you should get, there’s 3 points to consider:

  1. If you have a longer neck, go with crew necks. A v-neck would visually lengthen your neck and make it look longer. Unless you can find shorter v-necks with a shorter “v” like the white shirt on my model below.
  2. If you have a shorter neck, go with v-necks. It’ll make your neck appear a little longer.
  3. If your neck is average, the t-shirt world is your oyster and you can have whatever you want!

What colors should I have?

Every man should have these colors to start since they’ll go with everything else in your Essential Wardrobe.

  • White
  • Heather gray
  • Navy
  • Black

As for how many of each you should have, I suggest getting at least 2 of each, that way you can easily get through a week without needing to do laundry.

Best T-Shirts For Men

Designer Options

The fabrics of these options are really amazing and super comfortable. The James Perse ones are a personal favorite and I use them on a lot of my clients. I wish I could make all my clothes out of some of these materials. See my note in the section below, before making your decision. All of these shirts come in the colors I recommended above.

Ralph Lauren Cotton Jersey Crewneck T-Shirt 

James Perse Melange Cotton Linen V-Neck

Rag Bone Navy Classic T-Shirt

James Perse Grey Crew Neck T-Shirt

Brunello Cucinelli Cotton Crewnect White T-Shirt 

Budget-Friendly Options

I’d probably default to these options over the designer ones because I find very minute differences between them. The biggest factors would be fit and slightly better fabrics. I don’t find the added costs are worth what you get in return, especially because t-shirts will need to be replaced much quicker than other items in your wardrobe. All of these shirts come in the colors I recommended above. I especially love the RibbedTee shirts and the American Apparel Summer Shirts.

All Saints White Figure Crew T-Shirt

Alternative Apparel Black Plain T-Shirt

Armani Exchange Pima Crew 

RibbedTee White Rex Cotton Modal Tee V-Neck 1-Pack

J.Crew Broken-in V-Neck T-Shirt

3 Best Ways to Wear Your V-Neck and Crew Neck T-Shirts

Alternative Apparel Black Plain T-Shirt

Burberry Slim Fit Wool Trousers

Allen Edmonds Park Avenue Oxford 

Tom Ford Black Snowdon Sunglasses

IWC Portugieser Automatic Watch

Rag & Bone Duncan Shawl Cardigan

RibbedTee White Rex Cotton Modal Tee V-Neck 1-Pack

Diesel Buster 0607A Jeans

Allen Edmonds First Avenue Dress Boots

John Varvatos Lafayette Sunglasses

IWC Portugieser Automatic Watch

Brooks Brothers Camel Suede Barracuda Jacket

RibbedTee White Rex Cotton Modal Tee V-Neck 1-Pack

SIimon Miller M001 Gunnison Slim-Fit Selvedge Denim Jeans

Nike Tennis Classic Sneakers

Tom Ford Black Snowdon Sunglasses

IWC Portugieser Automatic Watch

Men’s T-Shirt Outfit Ideas & Inspiration

The Polo Shirt

A Polo Shirt is a great, versatile item that I put all my clients in at some point of us working together. They’re timeless and a cornerstone of any good spring or summer outfit. I often recommend wearing them in place of t-shirts, as they give a casual outfit a bit of polish – which is never a bad thing. No matter your age or body type, every guy needs a few polo shirts in his wardrobe.

A good polo shirt will:

  1. Fit like a glove.
  2. Enhance the good parts of your physique and hide the imperfections.
  3. Make you look more polished and put together.
  4. Layer incredibly well.
  5. Only have short sleeves – long sleeved polos have no place in your wardrobe.

Fabric

Fabric choice is the biggest thing to consider when choosing a polo shirt and heavily dependent on your body type. The fabric you choose will determine how good (or bad) you look in a polo shirt.

Piqué Cotton

Piqué cotton polo shirts are made with cotton yarn and have thin ribbing visible in the garment. The texture is soft, and if you look closely you can see the tightly raised cords that give a waffle-like appearance.

Piqué polos are best for heavier-set men with wider physiques because the textured fabric hugs the body without conforming to the less flattering areas of the chest and stomach. When I’m working with a client who’s worried about his belly being accentuated, I always go with pique cotton. Think of the fabric as airbrushing your torso and hiding the problem areas.

Check out how much more flattering the piqué cotton polo is on the same guy compared to a cotton/silk blend polo. I bet his hands are covering his belly button divot in the cotton polo shirt picture, too. It’s an old photographer’s trick. Notice his chest area looks a little more smoothed out? Please don’t think I’m recommending this polo, it’s pretty bad (that’s a horrible sleeve length) but it highlights the “airbrushing” effect that piqué cotton has very nicely.

Pique Cotton Vs Cotton or Silk Blended Polos Ashley Weston

Cotton & Cotton Blended Polos

If you’re in decent shape, skip the piqué polos and grab a few cotton/cotton-silk blended polo shirts. The material looks better on your body type and is softer and more comfortable than pique cotton. These polos have a sleek, modern look that are great on their own or underneath a jacket. Beware, it’ll shine a spotlight on your body’s imperfections if you’re not in good shape!

SilkBLendPolo - Ashley Weston

Colors, Patterns, Piping, Etc.

Avoid any patterns or collar/sleeve piping and stick with the basic (and best) colors to begin. Grab a few white, black, navy, and charcoal/gray colored polos. They’ll give you the most versatility with the rest of your Essential Wardrobe and will work with any skin tone and body type.

If you’ve got the basic colors already, definitely get some brighter colors that compliment your skin tone and/or throw some stripes in there, too. I would universally avoid plaids or any other wackier patterns, it’s just too much and looks tacky.

To Tuck or Not To Tuck

If you’re wearing a polo shirt without a jacket, then don’t tuck your shirt into your pants. I know golfers do this, but you’re not on a golf course and it looks horrible tucked in.

If you’re wearing a jacket, then loosely tuck in the front part of the shirt by your belt buckle like in my 3 ways to wear images below. The shirt should still cover the top half of your belt buckle – you don’t want to completely see the buckle. I love doing this on my clients because it breaks up the outfit when you see a little of the belt buckle and gives it a little polish without overdoing it.

Leggo my Logo

Please don’t get a shirt with a huge logo all over it. Just. Don’t. Logos that are small and the same color of the rest of the shirt are passable, but if you have the option, go logo-less.

How Should A Polo Shirt Fit?

Check out my Men’s Polo Shirt Fit Guide for details.

The Best Polo Shirts for Men

Designer Options

For a pique polo, I recommend the Sunspel Riviera Polo Shirt. This shirt was made for Daniel Craig as James Bond in Casino Royale. A black or navy polo pairs well with either dark wash jeans or grey wool trousers. For a silk/cotton blend polo shirt, I love John Varvatos and Burberry. The shirt’s impressive construction and fit is well worth the price.

John Varvatos Hampton Polo 

Sunspel Charcoal Jersey Polo Shirt

Ermenegildo Zegna Mercerized Cotton Polo Shirt 

Burberry Navy Silk Cotton Polo

Theory Black Boyd Polo

Budget-Friendly Options

I’m a big fan of H&M’s cotton polo shirts. Actually, I would probably get those over the designer options a majority of the time. They won’t last forever, but they’re cheap enough to replace every season or two. They have a clean design with a great fit and a price that you can’t beat. The model in the first picture below is wearing the H&M Polo.

H&M Polo Shirt 

Uniqlo Navy Dry Pique Short Sleeve Polo Shirt

J.Crew Black Pique Cotton Polo

3 Ways to Wear a Polo Shirt

(Sunglass lenses sold separately)

H&M Polo Shirt

J.Crew Broken-In Chino in 484 Fit

Vans Authentic Sneakers

True Vintage Revival Glasses 

Polo-Shirt-Outfit-2-Ashley-Weston-Mens-Wardrobe-Essentials

The jacket and chinos are actually from Dsquared2, but they’re for an upcoming season and not available in stores at the time of writing. So I added the best substitutes below.

Philipp Plein Coat So Cool

Ermenegildo Zegna Mercerized Cotton Polo Shirt

Brooks Brothers Slim Fit Dark Khaki Garment-Dyed Chinos

Nike Tennis Classic Sneakers

Allen Edmonds Black Poplar Belt

IWC Portugieser Automatic Watch

John Varvatos Lafayette Sunglasses

 

Polo-Shirt-Outfit-3-Ashley-Weston-Mens-Wardrobe-Essentials

Burberry Modern Fit Wool Part Canvas Jacket 

Burberry Silk Cotton Polo Shirt 

Levis Chino 511 Slim Fit Jeans 

Salvatore Ferragamo Penny Loafer Shoe

Allen Edmonds Brown Poplar Dress Belt

Piaget Altiplano Watch

John Varvatos Lafayette Sunglasses

Outfit Inspiration