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.

3-Outfits-Every-Guy-Should-Own-Ashley-Weston-1-2

$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.

3-Outfits-Every-Guy-Should-Own-Ashley-Weston-1-4

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.

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

$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

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

POTW: What to Wear When Going To The Gym or Airport

I’ve been getting a lot of questions and emails from you about what to wear when going to the gym or airport so you’re still stylish, yet comfortable.

Thus, my POTW are John Elliott’s grey sweatpants because they’re the only item you need to add to your closet in order to create this sharp outfit below. You should already have three out of the four items if you’ve been following my Men’s Wardrobe Essentials Series for any length of time.

John Elliot Sweatpants POTW Ashley Weston

Here’s why this outfit is great:

Sweatpants

I love John Elliott’s clothes because he always does such a great job with creating high quality basics and these sweatpants are no exception. The construction and fabric choices are a cut above the rest, so if you’re able to swing it, I highly recommend these.

$190 – John Elliot Grey Escobar Lounge Pants (also in black)
$40 – Topman Grey Peached Skinny Joggers 

T-Shirt

You already should own a navy, black, and/or white t-shirt. These colors are perfect for the gym because they won’t show your sweat prominently like a grey tee will. Also, they look great with this outfit outside of the gym as well.

$80 – John Elliott Mercer T-Shirt
$30 – Armani Exchange Pima Crew

Jackets

Next, you should also already have a bomber jacket, whether it be navy or black, in your closet because as I’ve said before, bombers look great on every man, regardless of your age or body type. You can easily switch out the bomber for a zip-up hoodie if you want, but I wouldn’t change a single thing in this outfit.

$610 – Ami Navy Twill Bomber Jacket
$80 – Zara Technical Bomber Jacket 

Shoes

And finally, add some white tennis shoes or athletic sneakers from your closet to complete the look.

$120 – Nike Roshe Flyknit 
$75 – Adidas Stan Smith Sneakers

 

 

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

The 5 Shoes Every Man Should Own

In my Men’s Wardrobe Essentials Series, as well as my Summer Essentials Ebook, I touched on shoes a little bit, but the most-requested video/article for a while has been the number and type of shoes every man should own.

So here it is: These are the quintessential shoes that every man should have in his closet for year-round wear. Anything outside of these are specialty items, like snow boots, so they’re not included in this article.

 

1. Athletic/Running Shoes

Nike Roshe FlyKnit - Grey

Buy the Nike Roshe FlyKnit in gray

There’s nothing better than a sleek pair of athletic shoes. Not only can they function as your gym shoes, but they can  be worn with your casual outfits, as well.

I recommend sticking with a black/white, black/grey/white (like above), or navy/white color to ensure that your sneakers compliment all your outfits. Other crazy colors like neon green or a bright red will only draw attention away from your outfit which is why I’m not recommending those colors. You probably wouldn’t know it, but these shoes are one of my clients and almost a year old.

Since all of the shoes I’m recommending have white soles, I highly recommend Jason Markk’s Essential Shoe Cleaner Kit. Just give the soles a quick scrub with the included brush and soap every few weeks and they’ll look good-as-new for a long time.

Other Options

Nike SB Stefan Janoski Max
Adidas Pureboost LTD Shoe
Nike Roshe Two FlyKnit

 

2. White Sneakers

 

Buy the Adidas Stan Smith Sneakers

The second pair of shoes you should own, is what I’d consider an absolute essential to any well-dressed man’s wardrobe, which is why they were also included in my Men’s Wardrobe Essentials series.

They’re clean, classy and look great with a lot of your casual, even up to a little more dressy, outfits. Throw on a nice fitted blazer and some dark wash jeans with them and they’ll look amazing. See here for outfit inspiration images.

Under no circumstance should you wear these with a suit, though. That’s a trend that’s been floating around for a few years and I just think you’re not doing a suit justice by dumbing it down with sneakers.

A quick note, because it’s been brought up in the comments of my White Sneaker Video – Jordan’s and Air Force Ones are not the same as these – even if they’re white – because the shape and profile of those shoes are completely different. Notice how sleek and simple the profile of the above shoe is – THAT’S what makes all the difference. Jordan’s and Air Force Ones are chunky looking and have a very specific look that a lot of men can’t pull off.

Designer Options

 

Saint Laurent leather sneakers
Acne Studios leather sneakers
WANT Les Essentiels de la Vie leather sneaker
Common Projects BBall leather sneakers

Budget-Friendly Options

Converse Chuck Taylor All Star II Ox’ Canvas
Converse Jack Purcell Sneaker
Nike Tennis Classic Ultra Leather
Vans Authentic Sneakers

 

3. Suede Driving Moccasins

 

Tod's Gommino Driving Shoes in Suede

Tod’s Braided Tie Drivers

The third pair of shoes you should own are suede driving moccasins. I’ve already covered these in my Summer Essentials Ebook, but they’re also great shoes during the other parts of the year, depending on your climate.

If you’ve never worn a pair, then you really should try them because they’re the most comfortable middle ground between a dress shoe and a sneaker and after they’ve been broken in a little bit, they’ll feel like you’re wearing a pair of socks.

I have these ones here by Tod’s that I really love. Stick with dark brown first, then you can add a tan color and then navy which will cover you for any outfit you can wear outside of a suit – which you should never wear driving mocs with. The construction is fantastic and they hug your feet nicely –
which is important because a lot of cheaply made driving mocs tend to look loose around your feet which is to be avoided.

There’s three things to remember about driving moccasins:

Only wear no-show socks with them. I did a whole video about socks so check out the link in the video description.
Before you wear them for the first time, make sure you Scotchguard them in order to protect the suede from dirt & liquids as much as possible.
They’re going to get dirty, it’s inevitable with suede. So buy them knowing they’re going to have a shorter shelf life than the rest of your shoes, but trust me, you won’t care because they’re so damn comfortable.

Designer Options

Tod’s Textured Suede Tie Drivers
Tod’s Braided Tie Drivers
Prada Suede Slip-On Moccasin, Oltremare
Brook’s Brothers Suede Driving Mocs

Budget-Friendly Options

Jack Erwin Parker Driving Loafer 
FRYE Russel Venetian
Johnston & Murphy Perforated Driving Loafer 

4. Oxford Or Derby Dress Shoes

ferragamo-marte-plain-toe-derby-ashley-weston1

Prada Plain Toe Blutchers

The fourth pair of shoes you should own are Oxford or Derby dress shoe with a sleek profile and round toe. I’ve covered these extensively before, but every man needs at least a black and possibly brown pair of dress shoes in his wardrobe. They go well with all outfits outside of a super casual outfit (think: t-shirt and jeans). And since you should at least own one suit, these are necessary because you can’t get away with wearing any other shoes with your suit. Remember: the goal is to have you looking amazing, no matter the scenario or outfit.

I prefer plain toe, but you can also get cap toes, but I will grab a pair of plain toed Oxfords or Derbys over any other kind of dress shoe 99% of the time.

As for brogueing, burnished toes, oxblood or other unique colors, don’t get me wrong, I love them, but that’s like two levels down the road if you’re new to dressing better. They’re very specific and won’t go with a lot of your outfits, so grab them after you’ve invested in a classic black and dark brown oxford.

Designer Options

Giorgio Armani Plain-Toe Patent Leather Bluchers
Allen Edmonds Park Avenue Cap-Toe Oxfords
Allen Edmonds Carlyle
Prada Plain Toe Blutchers

Budget-Friendly Options

Aldo Craosa 
Jack Erwin Joe Cap-Toe Oxford
Johnston & Murphy Hyde Park ll Cap-toe

5. Brown Leather Boots

Purdey Brown Men's Grain Leather Boot With Dainite Sole

Crockett & Jones Islay Wingtip Boot

The final pair of shoes – in this case – boots you should own are a pair of brown leather boots.
They’re utilitarian in that you can wear them in a lot of adverse weather situations as well as in more elevated casual outfits. I prefer brown because boots are usually more geared toward the cooler months, and brown is a great fall/winter color and it goes AMAZINGLY well with the dark wash jeans and wool trousers you should already own. But don’t be mistaken, you can also wear these year-round.

It’s been asked this a few times by viewers, so unless you’re going for the lumberjack or American/Japanese worker-style look, don’t wear these boots with a suit because these ARE NOT DRESS BOOTS.

I love the pebbled brown leather and goodyear welting of the Purdey boots above, which is why they’re my top choice. Trust me, I spent a lot of time finding the best boots out there and these are hands down my favorite.

If you want to know how to tie your boots properly like this so don’t have a bunch of excess laces flopping around, check out my video about how to properly tie men’s shoelaces.

Designer Options


O’Keefe Algy Split-Toe Weatherproof Pebble-Grain Leather Boots
Crockett & Jones Islay Wingtip Boot

Frye Jones Lace Up Boots

Budget-Friendly Options

Aldo Acerrassi
Johnston & Murphy Karnes Cap Toe Boot
Aldo Etausen Boots
Wolverine 1000 Mile Boot 

How To Cuff Pants

Lots of readers/viewers have been asking me to do an article and video about how to roll or cuff men’s pants, so I’m finally doing it! The article is great and all, but the act of rolling your pants is not something easily shown in still images, so do yourself a favor and watch the video below for the fully experience.
 
With the exception of jeans and boots, you should only be rolling your pants in the spring and summer, unless you’re in a climate where it’s warm all year-round. This is very much a warm weather flair to add to your dark wash jeans, chinos or khakis or even wool pants and trousers. But it is a little odd to wear during the colder, winter months.

How To Quickly Measure Cuff Width

Before we begin, let me show you a quick and dirty way to figure out the proper width of your cuff by using your finger joints. The each joint of your index finger is roughly an inch long.

Finger Joint Ashley Weston Cuff pants

So if you need the cuff width to be about 2″ wide, the top of the cuff would hit right around the second or middle joint, like in the picture below:

How to Cuff Pants Men Roll - Ashley Weston - Finger Measurement
 

The Simple Cuff

TheSimpleCuff-AshleyWeston-Jeans-Pants-Chinos-Denim-Joggers
This cuff works especially well with slim fit jeans. I like to use this cuff when I’m going for a cleaner, sleeker look with a client. I’d caution against using it with chinos or other pants, as the fabric can be a little floppy around the ankles.

You also want to avoid using this cuff if you’re wearing straight fit jeans because your ankles will be swimming in a bunch of fabric. Use the pinroll cuff in the next section, instead.

Before you start cuffing, you should already have your jeans and shoes on. Otherwise, it’s harder to tell what the finished product looks like and if you’re showing the right amount of ankle. Hopefully you’ve already seen my men’s jeans fit guide so you know that your slim fit jeans should have a slight break at the hem. This cuff won’t look right with any other type of pant break.

How to Cuff

Low Top Shoes

If you’re wearing low top shoes, roll up your jeans’ cuff once.
The cuff width should be between 1.5” to 2”. If you’re on the shorter side, get the cuff as close to 1.5″ as possible. If you’re on the taller side, go for 2″. This will maintain the proper promotions for your body type.
Cuff Pants Simple Roll Ashley Weston

Make sure that the roll is the same width or thickness on the front and back of the pants before you do the second roll. After finishing the second roll, the bottom of the cuff should just hit the top of your outer or inner ankle bone, like in the image below:
Ankle Bone Simple Cuff Pants Ashley Weston

Boots or High Top Shoes

It’s the same as low tops: do at least 2 rolls and make sure to maintain the 1.5″ to 2″ cuff width, depending on your height.

The bottom of the cuff should either lightly graze the top of the shoe or boot or go a little bit past the top of the boot or high top. The image below, has the pants rolled up 3 times on the left and 2 times on the right. Both are equally acceptable lengths. I prefer 2 rolls, as 3 makes it look a little too military for my tastes, but 3 is just fine if that’s what you prefer.

Cuff Pants Roll Pants Ashley Weston BootsRoll

 

The Pinroll Cuff

The Pinroll Pant Roll Cuff - Ashley Weston
This cuff is great for any cut of jeans, as well as chinos. I like this roll because it eliminates the issue of your pants swimming around your ankles when they’re cuffed.

Again, start with your pants and shoes already on. Check my men’s jeans fit guide and chino pant fit guide for details about the type of break your pants should have before cuffing. If your pants aren’t fitting properly or they’re too long at the hem, the roll will look big and chunky around your ankle, which you don’t want.

How to Cuff

Low Top & High Top Shoes and Boots

To start, pinch the fabric on the inside of your ankle so it feels slightly snug against your leg or ankle.
Cuff Pants PinRoll Pinch Ashley Weston

Now fold the fabric over towards your heel. The reason why we do this is because it hides the fold better than if you folded the fabric towards the front.
Cuff Pants PinRoll Roll Back Ashley Weston

With your thumb still holding the fold against your ankle, start rolling the cuff up with both hands. Make sure the roll is between 1 to 2 inches wide. If you’re on the shorter side, keep it around 1″ and go closer to 2″ wide if you’re taller. This will maintain the proper proportions for your stature.
Cuff Pants PinRoll 1st roll Ashley Weston

Now roll up the cuff a second time. You want to roll at least twice to make sure that excess fabric that we folded over won’t come undone. It won’t stay with just one roll.
Cuff Pants PinRoll 2nd roll Ashley Weston

if you’re wearing low tops, you want the bottom of the cuff to hit around 1.5 to 2” above your outer ankle bone, like the image below. If you need to roll 3 times to get there, do that.

The Pinroll Pant Roll Cuff - Ashley Weston

The only exception to the 3 roll maximum is if you’re wearing boots or high tops. Then you need the cuff to just cover the top of your boot or lightly graze the top of your high tops when standing up. The image below has the cuffs rolled twice.

Boots Pinroll Ashley Weston

That’s it! Now cuff all the things!