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 

The White Sneaker

This article is part of my Men’s Wardrobe Essentials series.

White Sneakers AKA Tennis Shoes are like jeans – everyone has them, but not everyone has the right ones or knows what to do with them.

Sneakers look good with any casual outfit (no suits, PLEASE!) and your color choice and how you care for them will have a big impact on whether you’ll look sharp, or just… blah. 

Why White Sneakers?

If you’re reticent about white sneakers, I get it. My clients are a little freaked out by them in the beginning, too. But the reason I prefer white is they look super sharp and literally go with everything you’d wear casually. A pair of white sneakers instantly elevates an outfit to be a little sharper than it would be with other casual shoes. In my book, that’s a good thing.

As a woman, when I see a sharp-looking guy, I want to learn more about him. It’s impressive and intriguing. I’ve been busted for staring a few times because of this 🙂

If you really, really don’t want to get white shoes, go for a navy color then. They’ll still go with a lot of the other essentials on my list, but not as well as white.

High Tops or Low Tops?

For a foundational piece like this, leave the high tops for later. They’re not appropriate in many occasions where low tops are. High tops are definitely more sporty looking and with pants will bunch up around the ankles and can create a lot of stacking.

Canvas vs. Leather

This is when I’ll leave it up to your preference. Either one will work for the same occasions and outfits. Some people prefer natural fibers over leather. I prefer leather because it doesn’t stain as easily and they’re easier to keep clean, but they’re also (slightly) more costly. It’s entirely up to you. I’ll provide both options below.

Cleanliness is next to Godliness

I’m always shocked to learn that most guys don’t know that women look at 3 things, in this order, when first meeting a man:

  1. Your face/head (duh!)
  2. Your fingernails
  3. Your shoes

Dirty or worn out shoes are a major turn off. Spend 30 seconds and take wet cloth or a Magic Eraser sponge and give your shoes a quick wipe down. A little effort goes a long way and will keep your shoes looking good for much longer.

The Best White Sneakers For Men

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
Vans Authentic Sneakers
Adidas Stan Smith Sneakers
Nike Tennis Classic Ultra Leather 

3 Ways To Wear

Topman Bomber Jacket
Armani Exchange Pima Crew Tee
J Brand Tyler Fit Jeans Keckley
Converse Jack Purcell Sneaker

H&M Polo Shirt
H&M Chinos Skinny Fit
Vans Authentic Sneakers
True Vintage Revival Glasses

Burberry London  Slim Fit Travel Tailoring Wool Jacket
Brooks Brothers Merino Wool Sweater
Brooks Brothers Non-Iron Milano Fit Button-Down Collared Dress Shirt
J Brand Tyler Fit Jeans Keckley
Brooks Brothers Silver Buckle Leather Dress Belt
Converse Jack Purcell Sneaker

White Sneaker Outfit Inspiration/How To Wear White Sneakers

The Dark Wash Jean

Jeans, Denim, Blue Jeans, whatever you call them – the bottom line is that they’re a staple in every man’s wardrobe. But that doesn’t mean most guys know how to choose the right pair.

Every day, I see looks of dissapoinment slapped across people’s faces as the men in their lives waddle around in poopy-pants, flop about in the moo-moo version of jeans or show off their twig and berries.

Let’s fix this.

Every single man, no matter their size, age or body type should have a few pairs of dark washed jeans in their closet. They work for nearly all occasions outside of a formal setting and look good with virtually everything- especially my list of men’s wardrobe essentials. They’ll never steer you wrong and are likely the pants you’ll wear a majority of the time.

The 5 Aspects Of Jeans

1. Wash or Rinse

This dictates how light or dark the jeans are as well as how they’re treated. Light wash = lighter colored. Dark wash = dark.

My preferred wash is dark blue, sometimes called indigo, depending on the brand.

Because of the title of this article, you know I’m recommending that you own dark wash jeans. The reason is because this wash looks great on everybody, hides skinny or thicker legs better than any other color and can be dressed in a casual or less-casual way. I love them so much that I put them on every single one of my clients.

2. Style

This is also called the “cut” and sometimes also called the “fit” of the jeans. Depending on your body type, you should be wearing a certain style. We’ll get into that in a minute, but the most common styles are (in order of slimness):

  • Skinny
  • Slim
  • Straight
  • Boot Cut
  • Relaxed

3. Size

The waist and inseam (leg length) measurements of the jeans. Ex: 32×32 (inches).

If you’ve seen my Fit Guide, you know appropriate jeans sizing, but here’s a quick refersher:

  • They should fit your waist without needing a belt. They can even be slightly tight, as denim will loosen as you wear them.
  • The inseam (length) should leave a slight or full break where they meet your shoes. Anything shorter will look odd and anything longer will bunch at your ankles and throw off your proportions.

4. Denim Type Or Fabric Blend

Denim material can be blended with a variety of other fabrics. Some jeans may have two to three percent spandex and others might have polyester blended into them.

A quick thought if you go with spandex blends:

  • Spandex blends, while a little more comfortable and forgiving in the thighs, tend to stretch out and not retain their shape as well as 100% cotton blends. I’ve definitely seen some “poopy pants” as a result of this.

It’ll depend on what you prefer, I can go either way on this – some of my recc’s below are blends, some are 100% cotton.

5. Fit

I get asked all the time “How should men’s jeans fit?”

Here’s the the trifecta of how your jeans should fit, regardless of age or body type:

  • You should be able to pinch a minimum of 1 inch of fabric, but no more than 1.5 inches on either side of the thigh.
  • They should fit your waist without a belt.
  • They shouldn’t be too short or too long – having a slight or full break. 

Check out my Fit Guide for more in-depth info.

The Best Dark Wash Jeans For Your Build

A quick note about your height: It doesn’t matter. My clients range in size from 5ft 3in to almost 7ft and I’ve never put them in different jeans because of their height. These are the best jeans for short men, tall men, medium-sized men and so on. The only thing that matters is your build: slim/regular or larger.

Slim or Regular Build

You’ll want to get a “Slim” fit. Slim-fit jeans tend to slightly hug the thighs, knees, and calves while tapering down from your knee to ankle.

A lot of my slim & regular built clients initially believe this style will make them look too skinny. This couldn’t be further from the truth. It’s just that they’re used to wearing super baggier clothes to try and hide their slimness, which, coincidentally, just makes them look slimmer. A proper fitting pair of jeans just looks right, regardless of your build, and doesn’t make you look one way or another – I promise.

Things to avoid:

  • Don’t make the mistake of thinking “Skinny” fit is the same as “Slim” fit. “Skinny” fit jeans are usually skin-tight and not appropriate
  • Avoid “Straight Fit” jeans. Like the name implies, the leg of the pants are looser and will be cut straight down from the knee to ankle. This cut will look terrible on you. 
  • If you can pinch more than an 1.5 inches of denim on either side of your thighs, you need to move down to a slimmer cut or get the legs taken in. If you can avoid it, don’t rush to the tailor. Try a size down first or another brand. This is costly for a tailor to do. Having too much fabric on your thighs will make you look smaller, shorter or wider than you are.

Designer

I’ve personally worked with and touched each pair of these jeans (in all sections) and they’re awesome. The fit is very accurate, the pocket placement and stitching is great. Diesel runs a little larger in the waist, so go down a size (ex: if you’re a 34 waist, get a 32).

Tom Ford Slim-Fit Stretch Indigo Denim Jeans
RRL Slim Fit Selvedge Jeans
JBrand Tyler Taper Fit in Rasalas
JBrand Taper Tyler Fit in Blue Hood
Diesel Buster Jeans

Budget Friendly

I love these because the quality in relation to the price is very good and you can never go wrong with a classic like Levi’s and I love Uniqlo’s wash and they also offer free hemming!

Uniqlo Stretch Selvedge Slim Fit Jeans
Levi’s 511 Slim Fit Stretch Jeans

Larger Build

The classic “Straight-Leg” fit is perfect for you. No matter a man’s build, but especially in your case, it’s all about balancing your body’s proportions to make sure your bottom half complements your upper half.

There are a few great brands out there that offer straight-legged jeans with a slightly roomier thigh area which will hopefully solve your frustrations with finding jeans that fit properly.

Things to watch out for:

  • Avoid any cut of jean (all pants in general, for your build) with a taper in the legs. A taper will make you look really top heavy.
  • If you can pinch more than an 1.5 inches of denim on either side of your thighs, you need to move down a size, go to a slimmer cut, try a different brand, or get the legs taken in by a tailor. Don’t get the legs taken in if you can help it, it’s costly for a tailor to do. Having too much fabric on your thighs will make you look wider than you are and completely throw off your proportions.

Designer

The wash, quality and fit of these are great and I use them all the time for my larger clients because it makes them look really sharp.

AG Graduate Jeans
JBrand Kane Jeans 

Budget Friendly

Just like I said for the slim to regular built options in this category: I love these because the quality in relation to the price is very good and you can never go wrong with a classic like Levi’s and Uniqlo’s wash is great and they offer free hemming!

Levi’s 514 Tumbled Rigid Jeans
Uniqlo Selvedge Straight Leg Jeans
Gap 1969 Straight Fit Jeans

3 Ways To Wear

Ashley-Weston-Dark-Wash-Jeans-Look-1-Full

Levis Sunset Pocket Tee
JBrand Tyler Taper Fit in Rasalas
Allen Edmonds Wide Basic Belt
Vans Authentic Sneakers

Ashley-Weston-Dark-Wash-Jeans-Look-2-Full Ashley-Weston-Dark-Wash-Jeans-Look-2-Detail

Brooks Brothers Suede Barracuda Jacket
J. Crew Garment-Dyed Henley
JBrand Tyler Taper Fit in Rasalas
Allen Edmonds Wide Basic Belt
Vans Authentic Sneakers

Ashley-Weston-Dark-Wash-Jeans-Look-3-Full Ashley-Weston-Dark-Wash-Jeans-Look-3-Detail-2 Ashley-Weston-Dark-Wash-Jeans-Look-3-Shoes

Modern Fit Travel Tailoring Virgin Wool Suit
Brooks Brothers Red Fleece Spread Collar Sports Shirt
JBrand Tyler Taper Fit in Rasalas
The Tie Bar Knitted Tie
The Tie Bar Cotton Pocket Square dark Charcoal Tipping
Johnston & Murphy Fielden Cap-Toe Dress Shoe
IWC Portuguese Automatic Watch

Outfit Inspiration