3 Outfits Every Guy Needs

My articles and videos almost always center around a specific piece of clothing or accessory, so I thought it would be fun to switch it up and talk about 3 head-to-toe foundational outfits every guy needs. Once you have these 3 outfits, you can build an entire wardrobe around them. And here’s the beauty of them: from these 3 outfits, you can switch things in and out to add your own personal touch and truly make them your own.

Outfit 1

The first outfit is a casual one, comprised of a black polo shirt, a well-fitting pair of dark wash jeans and some white low top sneakers. This is a solid casual outfit that will always look great and put together on every man, regardless of your age or body type.

3-Outfits-Every-Guy-Should-Own-Ashley-Weston-1

$40 – J. Crew Broken-In Slim Polo Shirt in black
$10 – H&M Polo Shirt Slim Fit in black (**THESE ARE THE BEST POLO SHIRTS!!!!)
$228 – J. Brand Tyler Taper Fit in blue hood
$70 – Levi’s 511 Slim Fit Stretch Jeans in blue flame
$410 – Common Projects Achilles Leather Sneakers
$75 – Adidas Originals Stan Smith 
$415 – Tom Ford ‘Snowdon’ Sunglasses
IWC Portugieser Automatic Watch

Outfit 2

I like to call this outfit ‘dressy casual’ because it transitions well from day to night. Throw on a leather or cotton black bomber jacket with a black t-shirt, dark wash jeans and black leather chukkas.

If you’re thin to average build, you can also wear a white t-shirt. However, if you’re a broader man that’s not in shape, and you decide to take off your jacket, then a white t-shirt will actually spotlight how big you are (and not in a good way). Also, the reason why you want to go with black chukkas is because black is the dominant color in your jacket. I went with leather chukka boots over suede and lace-up boots because the latter options won’t look appropriate for every season.

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$620 – All Saints Zeno Leather Bomber Jacket in black
$200 – Zara Leather Jacket
$90 – James Perse Clear Jersey Crew in black
$30 – Armani Exchange Pima Crew in black
$170 – Diesel Buster 0607A Tapered Jeans
$70 – Levi’s 511 Slim Fit Stretch Jeans in blue flame
$175 – Johnston & Murphy Conard Cap Toe Chukka in black

Why a bomber over a blazer?

A bomber is a very stylish, modern alternative to a blazer that works in almost all the same occasions and looks great for every man, regardless if you’re a teenager all the way to a retiree. A younger gentlemen in high school or college, for instance, wouldn’t necessarily need a blazer, so that’s why I’m not recommending it over a blazer. If the occasion does call for a sport coat or blazer, in a pinch, you can use the jacket in my next recommendation and dress it up like I did in the picture below.

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Outfit 3

Lastly, my classic go-to formal outfit is a charcoal or navy suit with a white semi-spread collar dress shirt, black or charcoal tie, white pocket square, and oxford dress shoes. If you’re going with a charcoal suit, then pair with a black tie and black dress shoes. For a navy suit, pair with a charcoal tie, and dark brown dress shoes.

I love these two suits because it’s very easy to go formal by adding a tie or dress them down by forgoing a tie or swapping in a t-shirt instead of a collared shirt.

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$1395 – Burberry Slim Fit Wool Part Canvas Suit (navy)
$425 – J.Crew Navy Ludlow Suit Jacket in Italian Wool (navy and charcoal)
$225 – J.Crew Navy Ludlow Suit Pant in Italian Wool
$90 – TopMan Grey Slim Fit Suit
$280 – Allen Edmonds Carlyle Plain-Toe Oxfords (black or brown)
$275 – Johnston & Murphy Hyde Park II Cap-Toe (black or brown)
$19 – The Tie Bar Grenafaux Tie (black or charcoal)
$10 – The Tie Bar Solid White Cotton Pocket Square

POTW: Johnston & Murphy Burgundy Cap Toes

I was prepping for a fitting, and I came across these Johnston & Murphy burgundy cap toes that I thought you should know about. I’m not normally a fan of burgundy shoes because I often find the color to be difficult to wear and usually ends up being too much of a statement piece. But, these are different because the darker color is closer to a burgundy brown instead of the more reddish-oxblood color you often see with other “burgundy shoes” and that makes them much easier to wear. So, I had to make them my pick of the week!

 

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$155 – Johnston & Murphy Burgundy Conard Cap Toe 

Best Ways to Wear

The decorative broguing along with the brown soles adds a casual look to them making them easy to wear with your summer suits, like a green or navy cotton suit, or with some chinos or dark wash jeans. Blues, greens, and khaki go great with burgundy. If you’re ever unsure how to wear these, just know that whenever you wear brown dress shoes with a more casual outfit, you can easily wear these instead.

I also want to address the contrasting stitching. On more formal shoes it can be very distracting and pull the attention away from your outfit and really focus it on the shoes. But on a casual dress shoe, such as these, it works because you’re never going to be wearing them with a really formal outfit. So if you’re thinking about doing that, then please don’t.

Like I’ve said before, accessories are a great way to add some fun touches to your outfit and these shoes do exactly that.

BurgandyCapToeOutfits_AshleyWeston

 

Look 1

$40 – J. Crew Slub Cotton Deck-Striped T-Shirt
$68 – J. Crew Navy or Green Stretch Chino Pant in 770 Fit
$30 – Uniqlo Slim Fit Flat Front Chino in Navy

Look 2

$69 – Brooks Brothers Selvedge Oxford Sport Shirt
$70 – Levi’s 511 Slim Fit Stretch Jeans (in blue flame, dark hollow and stump town)
$228 – JBrand Tyler Fit in Blue Hood

Look 3

$358 – J. Crew Ludlow Suit Jacket in Italian Cotton Oxford
$188 – J. Crew Ludlow Suit Pant in Italian Cotton Oxford
Shirting – See my dress shirt article
Ties – See my ties article

16 Accessories Every Man Needs

These are, to me, the 16 accessories every guy needs to own, regardless of your age, occupation, and lifestyle. Some of these items you may not wear often, but there will be an occasion, as a grown man, when you will need them and you’ll be thankful that you thought far enough ahead to take care of them before it’s too late and you’re scrambling at the last minute. I’ve also included my favorites for each of these items below. But these points below are just skimming the surface compared to the much more through Men’s Essential Accessories Series I did recently.

16. White Pocket Square

Like I’ve mentioned before, every man should have at least a grey suit. Even if you only wear it once every year, you’re going to need a suit. Along with that, looking well dressed is always about the details and a white pocket square is an easily overlooked item that really does make a big impact and it’ll only set you back a couple of bucks.

White Pocket Square Ashley Weston

$175 – Tom Ford Solid Classic Silk Pocket Square
$60 – Boss Solid Silk Pocket Square
$10 – The Tie Bar Solid White Cotton Pocket Square

15. Silver Tie Bar

This is another overlooked item. I talked about this in my article about the 12 Things Men Wear That Women Love, but a tie bar is something that adds that special touch to your outfit. It’s also so cheap to own so order it once and you’ll never think about it again.

Silver Tie Bar Ashley Weston$15 – The Tie Bar Silver Shot Tie Bar
$70 – J. Crew Sterling-Silver Tie Clip 

14. Solid Black and Navy Tie

These two ties will work for any suit you have in your closet, making them an absolute must have. Make sure the width of your tie complements your body type.

Black and Navy Tie Ashley Weston

$19 – The Tie Bar Grenafaux Tie (available in black and navy)
$60 – J. Crew American Wool Navy Tie
$60 – J. Crew American Wool Black Tie

13. Dress Socks

Get rid of your white socks. These socks can and should be worn as your everyday socks. If you need heavier duty, thicker socks for your job or because of the weather, there are plenty of companies that offer warmer versions.

Solid or Patterned Dress Socks Ashley Weston

$4 – Uniqlo Argyle Socks
$20 – Brooks Brothers Egyptian Cotton Jersey Knit Crew Socks
$15 – J. Crew Tipped Microstriped Socks

12. Sunglasses

Whether you’re a sunglass man or not, sunglasses are important because they’re going to protect your eyes from the sun, prevent you from squinting, which creates wrinkles around your eyes, and they can add a stylish, cool touch to your outfit. Check out my sunglasses story so you choose the right frames for your face shape.

Sunglasses 1 Ashley Weston 2

$415 – Tom Ford Snowdon Sunglasses
$98 – J. Crew Jack Sunglasses
$95 – Warby Parker Winston Sunglasses 

11. Baseball Hat

We all have those lazy days, myself included, where you just say F it, I’m gonna throw on a hat. When it comes to baseball hats I have very specific opinions about them so I shared some of my recommendations below.

Baseball Cap Ashley Weston

$48 – Gents ‘The Directors’ Baseball Cap
$22 – Flexfit Blank Snapback 2014

10. Black and Brown Oxford or Derby Shoes

Not only do these oxford dress shoes look great with your suit, but they also look nice with chinos, jeans, and trousers when you want to dress up a more casual outfit.

Black and Brown Shoes Ashley Weston

$395 – Allen Edmonds Carlyle Plain-Toe Oxfords
$750 – Prada Plain-Toe Bluchers
$175 – Johnston & Murphy Melton Cap Toe Oxfords

9. Black and Brown Dress Belts

Since you’re going to own dress shoes, you absolutely need to match your leather belt to your shoes.

Black and Brown Dress Belt Ashley Weston

$98 – Brooks Brothers Leather Dress Belt
$98 – Allen Edmonds Poplar Dress Belt
$25 – H&M Leather Belt

8. Weekender Bag

Everyone travels. Whether it’s to some exotic country, or across town, you’ll need to put your clothes in something AND trash bags are not an option. Like every accessory you own, it should not only serve it’s purpose, but look damn good at the same time. I have a whole article about weekender bags you should check out.

Weekender Bag Ashley Weston$965 – Frank Clegg Signature Travel Duffle (in black, chocolate or chesnut)
$800 – Killspencer Weekender 3.0 (in black leather or charcoal grey leather)
$115 – Everlane ‘The Dipped Weekender’ (in black/black, navy/black or reverse denim/black)

7. Dopp Kit

This item goes great with your weekender bag. Again, doesn’t matter if you’re traveling to another city or to the gym, a dopp kitt is essential because it’ll keep your grooming products organized and contained in a respectable manner.

Dopp Kit 1 Ashley Weston 2

$148 – Jack Spade Mason Leather Zipper Top Dopp
$300 – Shinola Travel Kit
$200 – This is Ground Tech Dopp Kit

6. Backpack or Briefcase with Detachable Strap

Depending on what you do for a living, if you live a more casual lifestyle or you’re a student, then a backpack is great. If you are in a more professional environment, a briefcase is best.

Backpack Briefcase Ashley Weston 1

Backpack

$800 – This is Ground Venture Regular Backpack
$210 – Cõte & Ciel Rhine Backpack
$120 – Aer Fit Pack Backpack 

Briefcase

$990 – Frank Clegg Zip-Top Briefcase
$895 – Shinola Slim Briefcase
$325 – Uri Minkoff Pebbled Leather Fulton Briefcase 

5. Casual or Dress Watch

Like the last point, which one you go with will depend on your lifestyle. Whether you’re a watch guy or not, any self-respecting man should own a watch or two.

Casual and Dress Watch Ashley Weston

Casual Watch

$7,000 – Rolex Submariner 114060
$3,400 – Omega Speedmaster Professional Moonwatch
$375 – Orient Diver Mako USA II

Dress Watch

$12,700 – IWC Schaffhausen Portugieser Automatic
$532 – Hamilton Intra-Matic Silver Dial Leather Watch
$195 – Tissot T-Classic Tradition Silver Dial

4. White Low Top Sneakers

Everyone has casual days, and white sneakers look so sharp on every guy regardless of your age or body type. If you’re really scared of wearing white, or think that it doesn’t look right, ease yourself into it with a nice low top lace-up black or navy sneaker.

White Sneakers 2 Ashley Weston

$370 – Acne Studios Adrian White Leather Sneakers
$75 – Adidas Stan Smith Sneakers
$65 – Converse Jack Purcell Classic Low Top

3. Boxer Briefs

All women find boxer briefs, specifically darker colors, so sexy on a man. And all men should be wearing them. Period.

Boxer Brief Ashley Weston

$26 – Exofficio Give-N-Go Boxer Brief
$13 – H&M 3-pack Boxer Shorts
$6 – Uniqlo Supima Cotton Boxer Briefs

2. Black and Brown Casual Leather Belts

Whenever you’re wearing jeans, chinos or shorts, throw on a casual leather belt because it’ll add a visually nice touch to your outfit.

Black and Brown Casual Belts Ashley Weston

$98 – Allen Edmonds Sun River Casual Belt
$295 – Salvatore Ferragamo Reversible Leather Belt 
$18 – H&M Leather Belt

1. A Quality Wallet

The things a man carries tells a lot about him and that’s no more true than with your wallet – check out my  article to the left for bifold, card cases, and phone wallet recommendations.

The below are only a few recommendations for bifold wallets.

Wallet Ashley Weston

$195 – Shinola Slim Bifold Leather Wallet 
$525 – Louis Vuitton Slender Wallet
$80 – Bellroy Low Down Wallet

Top 4 Shoes For Spring Men

Top 4 Men’s Shoes for Spring

These are the top 4 men’s shoes for Spring that I really love. You’re probably not going to wear these with your Fall and Winter wardrobe, so it’s time to pull these shoes out of your closet and let them shine! Footwear is a great way to inject new life in your existing wardrobe, and these 4 shoes will make a stylish statement during Spring and Summer. 

Here are my top 4 favorite shoes for Spring:

4. Suede Double Monk Straps

I included these in my Top 10 Essential Items for Spring as well. 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!

 

$685 – Crockett & Jones Lowndes Espresso Calf Suede
$398 – Brooks Brothers Suede Double Monk Strap
$275 – Crosby Square Conley Double Monk Strap (Espresso and Navy)
$80 – H&M Suede Monkstrap Shoes

3. Penny Loafers

I absolutely love penny loafers. They look so good when worn with no-show socks and a little bit of ankle exposed. Whether you cuff your jeans or chinos, or hem your pants so there’s no break or a little ankle showing. A leather loafer looks so chic and luxurious. I love Ferragamo’s loafers (I got a pair for my fiancé 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.

Penny Loafers

$760 – Ferragamo Penny Loafer Shoe
$185 – Johnston & Murphy Stratton Penny

2. Suede Driving Shoes

Think of them as the middle ground between sneakers and penny loafers. They’re just as comfortable as sneakers, yet dressier like a penny loafer. I also included these in my Men’s Summer Essentials ebook because they work during the warmer months in general.

My hands down, favorite suede driving shoe is from Tod’s. Everything about that shoe – construction, design, and color choice – is so damn sexy and incredible. It’s worth every penny, and there is no close second for me.

 

$475 – Tod’s Gommino Driving Shoe (in brown, navy, and grey)
$115 – Jack Erwin Parker Driving Loafer (in navy, chocolate, caramel)

1. Navy or Grey Sneakers (Canvas or Leather)

Outside of your white sneakers, I love a great navy or grey low top sneaker. They’re neutral colors so you can wear them with everything you have and they definitely won’t get dirty quickly.

If you want to splurge, Common Projects makes my favorite sneakers and a close second are by Lanvin.

 

$570 – Lanvin Shiny Cap Toe Sneaker (in navy or grey)
$509 – Common Projects Achilles Low Premium in Grey (or navy suede)
$75 – Converse JP Jack Sneaker (leather)
$65 – Converse Jack Purcell Ox Sneaker (canvas)

Henley Shirts

Henley shirts are one of the few items that, to me, don’t really have a specific season they’re best worn in because there’s so many different versions for men. Other shirts, like T-Shirts, Polo Shirts and Dress Shirts don’t really have this problem since they’re pretty standard across the board no matter the season.

I love henleys, because they look sexy and masculine, especially when the top 1 or 2 buttons are undone to draw the eyes to your chest and shoulders to show off your physique in a flattering way. Hence, the image below.

BUT, and this is a big mistake I see a lot of men making – they’re not for every everyone. More on that shortly.

Let’s get into what to look for in your henleys based on the time of year.

Intro - Short Sleeve Sexy henley

Fabric

Generally, henleys will be made out of cotton, so there’s really not much choice outside of that, but you still need to consider fabric weights depending on the time of year. The main thing to know is that lighter weights should be worn in warmer months or in warmer climates and thicker, heavier fabrics in cooler months or climates. You can get them in everything from a lightweight summer weave, where it feels like a t-shirt, to thicker, quilted versions which will keep you warm during the cooler months.

You don’t have to worry too much when buying them because, based on the time of year, the brands will carry the appropriate weights. But I still want you to be aware of it just in case.

Henley Fabric Ashley Weston 2

Fit

Like all your clothing, including henleys, they should have a trim fit throughout the body and arms – no matter your body type. You never want it too loose anywhere because that’s when you’ll look sloppy and not put together. You shouldn’t be able to pinch more than 1-2 inches of fabric on one side of your stomach and no more than an inch around the bicep.

The image below highlights the proper fit around the torso and sleeves.

Fit - Perfect fitting henley shirt

I mentioned earlier that henleys aren’t for everyone, so let’s get into that right now since we’re talking about fit.

For Thin Gentleman

If you’re a thin guy, no matter your height, if you want to wear a henley, you absolutely need to nail the fit, especially if you’re going to wear a long sleeve version. If the fit is too loose, it’ll make you look thinner and more frail than you are – not good!

I only like long sleeve henleys on thinner men if they’re layered underneath a jacket, like the below right image. When worn on their own, it really spotlights and elongates your thinner torso, like image on the left. So if you’re a thinner guy and want to wear a henley on its own, then wear a short sleeve version since it’ll look similar to your t-shirts.

Henley Fit Ashley Weston

Bigger Gentleman

If you’re a rotund gentleman (aka you’re not in the greatest shape and have a belly), you cannot wear a henley shirt, period. Allow me to show you why and explain. See exhibit A:

Fit - Big Guy - Bad Example of henley

Because of the button placket on the front, coupled with the lack of a collar, a henley will shine a massive spotlight on your bigger neck and torso. This is when a polo shirt is perfect and should be used instead, because a polo shirt’s collar will visually keep your torso balanced and in proportion, so your top half doesn’t look so big compared to your bottom half. The image below of James Corden shows a guy with the exact same body type as the image above, but in a polo shirt. Talk about a night and day difference…

Fit - Big Guy - Good Example - Polo Shirt1

Best Ways To Wear A Henley Shirt

Think of your short sleeve henley as a t-shirt, they’re interchangeable in the same outfits, so that means they can be worn on their own or underneath a jacket.

How To Wear Henley - Short Sleeve

J. Crew Slim Broken-In Short Sleeve Henley
J. Brand Tyler Taper Fit in Rasalas
Allen Edmonds Hampton Ave Tan Leather Belt 
I would pair this look with white sneakers – Nike Tennis Classic Sneakers

For a long sleeve, you would normally wear these during the cooler months as a layering piece, so I styled Dorian in a long sleeve henley shirt underneath a bomber jacket, dark wash jeans, and sneakers.

Mens-Henley-Shirt-Long-Short-Ashley-Weston-2

Mens-Henley-Shirt-Long-Short-Ashley-Weston-3

Burberry Lightweight Lambskin Bomber Jacket 
J. Crew Wallace & Barnes Wool Henley Sweater
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Black Dress Belt  
Johnston & Murphy Conard Cap Toe Black Chukka

IWC Portugieser Automatic Watch
Ray Ban RB4258 Sunglasses 

During the warmer months you can wear them with the sleeves pushed up. As I mentioned in one of my other videos, women LOVE to see sleeves rolled/pushed up around your forearms.

How To Wear Henleys - Henley Sleeves Pushed Up On Forearms

My Favorite Henley Shirts

Here are some great short sleeve and long sleeve (lightweight and heavyweight) henley options that I love.

Short Sleeve Henleys

Short Sleeve Henley 1 Ashley Weston

$125 – Rag & Bone Classic Short-Sleeve Henley
$35 – J. Crew Slim Broken-In Short Sleeve Henley (White, Navy, Heather Grey, Black)

Long Sleeve Henleys

Rag & Bone Long Sleeve Henley Ashley Weston

$250 – Rag & Bone Giles Merino Wool-Blend Heavyweight Long Sleeve Henley Shirt
$40 – J. Crew Slim Broken-in Lightweight Long Sleeve Henley
$15 – H&M Jersey Lightweight Long Sleeve Henley 

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.

Spring/Summer Suede Jacket Outfit

I came across this image that I thought would be a perfect Spring & Summer men’s suede jacket outfit because it’s a great, casual everyday outfit that you can wear when you’re going out with friends or if you work in a casual work environment. It has the added benefit of being able to be dressed slightly up or down as well as layered depending on the weather.

 

Jacket

A suede jacket is perfect for Spring and Summer and will look great on every guy, regardless of age or body type. But if you’re not into suede, or like other styles, look no further than the Harrington jacket or a wool bomber jacket.

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

Shirts

The plaid shirt underneath the grey sweater can be switched out for your classic white or blue oxfords or other fun colors or patterns like navy and/or green plaid or gingham.

$188 – J. Crew Albiate 1830 Ludlow shirt in red plaid
$139 – Steve Alan Masters Shirt
$92 – Brooks Brothers Non-Iron Milano Fit Mini-Madras Sport Shirt
$85 – TopMan SELECTED HOMME Navy And Grey Check Button Down Shirt

Crewneck Sweaters

On warmer days, you can ditch the crewneck sweater and just wear a collared shirt.

$298 – Brooks Brothers Golden Fleece 3-D Knit Fine-Gauge Merino Wool Crewneck Sweater
$158 – J.Crew Lightweight Italian Cashmere Crewneck Sweater (in heather dove)
$40 – TopMan Grey Ripple Textured Raglan Slim Fit Sweater 

Chinos

As for chinos, Spring and Summer is when you pull these bad boys out or you can swap them for a pair of dark wash jeans as well.

Make sure, that you know how either your chino pants should fit or how your jeans should fit, based on your body type.

$75 – J.Crew Broken-In Chino in 484 Fit
$30 – Uniqlo Slim Fit Chinos
$30 – H&M Chinos Skinny Fit

Shoes

Lastly, the brown suede chukka boots in the image are great, but you can also swap them out for brown monkstraps or even white sneakers.

$225 – Vince Camuto Branx Two-Eye Chukka 
$175 – Johnston & Murphy Conard Cap Toe Chukka 
$75 – Aldo Granges Chukka

Men’s Dress Shoes – Monk Straps, Brogues, Wingtips

Let’s talk about my favorite and what I consider the best men’s dress shoes for Fall and Winter – Monk straps, Brogues, and Wingtips.

Quick note: Wingtips are technically Brogues, so I’ll be lumping them together throughout this article. Just know when I refer to Brogues that I also mean Wingtips.

I prefer these during the cooler parts of the year because they go much better with the heavier wool and cotton items you wear in your Fall and Winter outfits. Don’t get me wrong, they also work year-round, but I think there’s better options out there for the other parts of the year. Check out my Summer Essentials Ebook and Wardrobe Essentials Series for details about those options.

Below are the things I look for in a good pair of Monk Straps or Brogues.

MATERIAL

As I said in my Fall/Winter boots story, I love a good calf skin. Don’t get me wrong, I love a suede monk strap or brogue, as well, but if you live in an area with snow or rain, you’ll regret the day you wear them outside. So let’s wait to get into those until Spring or Summer.

SHAPE

I will say this about dress shoes until the day I die, but you want a nice, slim profile with a rounded toe box. Ain’t nobody got time for square or large, bulky toe boxes! – See the video near the top of the article if you’re unsure about what they look like.

COLOR

As for colors, I love a nice dark chocolaty brown, or even a medium brown, like a walnut. Black is also good, but the first color I’d get is brown because it goes better with all the Fall colors in your wardrobe. All these colors are represented in my suggestions at the bottom of this article.

SOLES

If you live somewhere with a bit of rain, ice or snow, then you can and should definitely have these with Dainite or rubber inset soles for added traction. If you don’t live in that kind of climate, then a regular leather bottom that you’ll find on 99% of dress shoes is perfectly acceptable, but I’d probably look for a Dainite or rubber insert sole as my default. There’s also lugged soles, which are pretty popular right now (and I included some in my selects below), but I have a feeling they won’t be around for the long haul. They’ve already come and gone with fashion a few times in my lifetime. When it comes to Fall/Winter boots, though, I love me a lugged sole.

MONK STRAP SPECIFICS

I prefer a double buckle because a single buckle looks less refined. (Example in the video at the top).

If you get black Monk Straps, make sure the buckle is silver, because gold or brass tends to look gaudy, but is perfectly fine on brown monks (examples in the video).

Also, please make sure the buckles are on the smaller side as opposed to some big ass buckles you’ll find on a colonial gentleman.

As for medallion toes and other flourishes, I like all of them, so check out my recommendations below.

 

Best Ways To Wear Dress Shoes

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H&M Blazer Slim Fit
Burberry White Slim-Fit Poplin Dress Shirt
The Tie Bar Navy “Score Check” Tie
The Tie Bar Olive Green 1″ Tie Bar
The Tie Bar Grey Southeast Plaid Wool Pocket Square
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Dress Belt
Allen Edmonds Black Strand Dress Shoes
Tom Ford Snowdon Sunglasses
IWC Portugieser Automatic Watch

fallwinteressentialsdressshoesmonkstrapsashleyweston

fallwinteressentialsdressshoesmonkstrapsashleyweston2

Topman Light Brown Wool Rich Formal Coat
Burberry Slim Fit Cotton Poplin Dress Shirt
The Tie Bar Webster Medallions Tie
J.Crew Slim Merino Wool Cardigan
John Varvatos Grand Sunglasses
J.Crew Ludlow Suit Pant in English Donegal Tweed
Johnston & Murphy Nolen Double Monkstrap Shoes

Brogues & Wingtips

Budget Friendly

$130 – Aldo Bartolello
$165 – Johnston & Murphy Jennings Wingtip
$195 – Vince Camuto Tallden – Wingtip Oxford (2 colors)
$225 – Vince Camuto Benli Oxford

Designer

Allen Edmonds Strand Brown Cap Toe

$395 – Allen Edmonds Strand Cap-Toe Brown Oxfords with Dainite Rubber Sole

These, to me, are the quintessential Brogue. If you’ve seen my other dress shoe article then you know my love of Allen Edmonds. They make amazing products with great value – and they don’t pay me to say that. I’m just a huge fan.

I love this color and the Dainite soles. They’re just perfection.

$395 – Allen Edmonds McAllister Wingtip with Dainite Rubber Sole
$395 – Allen Edmonds Strand Cap-Toe Black Oxfords with Dainite Rubber Sole
$650 – Church’s Toronto Cap-Toe Oxford Brogues
$780 – Prada Runway Hybrid Wing-Tip Oxford 
$1,990 – Tom Ford Austin Cap Toe Oxford Shoe 

Monk Straps

Budget Friendly

Johnston Murphy Nolen Double Monk Strap Brown

$185 – Johnston & Murphy Nolen Double Monk Cap Toe

These hit all the points I look for in a double monk – the beautiful chocolaty brown with the matching soles, the silver hardware and the rubber tread inset for added traction. On top of that, they’re a GREAT price and my clients always comment about how comfortable they are. My other favorites are the Allen Edmonds Monks below, if you’re looking for something higher quality.

$99 – Kenneth Cole Regal Bearing Leather Monk Strap Dress Shoe (2 colors)
$160 – Aldo Caresien 
$225 – Vince Camuto Briant Double Monk Strap Shoe (2 colors) 

Designer

Allen Edmonds St Johns Black Double Monk Strap

$395 – Allen Edmonds St. Johns Black Double Monk Strap 


$395 – Allen Edmonds St. Johns Brown Double Monk Strap  
$395 – Allen Edmonds Mora 2.0 (3 colors)
$435 – Crockett & Jones Lowndes (2 colors) 
$700 – Brooks Brothers Peal & Co. Double Monk Strap