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.

Have questions? Curious what others think?

Join us in the comments section of the video above.

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 

James Bond Casual Style

This article & video is part of the Celebrity Style Inspiration Series, where Antonio Centeno from RealMenRealStyle.com and I pick out great outfits from movies and tv shows and demonstrate how to recreate and incorporate them into your wardrobe. 
As Antonio and I discussed in our other video about James Bond outfits to emulate, I really love the casual outfits Daniel Craig wears, so I wanted to recreate this one from Quantum of Solace, because it’s clean, simple and looks amazing on every guy, regardless of his age or body type.

Unlike the other video, where I switched out some items for more practical options, this one is already very practical, aside from the shoes. But we’ll get into that in a moment.

Here’s the full outfit I’m going to recreate. Apologies for the blurriness, but they don’t show this outfit for very long and the full-length shot is focused on a woman in a bikini to the right of Bond.

JamesBondQuantomOfSolaceChinosCardiganOutfitAshleyWeston

The Cardigan & Shirt

JamesBondQuantomOfSolaceChinosCardiganOutfitAshleyWeston1

Daniel Craig is wearing a black shawl collar cardigan which is so warm and comfy. I certainly wouldn’t advise wearing this during summer time, but for any other time of year, there’s nothing better than a shawl collar cardigan. I put my model in one from Todd Snyder, but check the outfit details at the bottom of this page, because Todd Snyder no longer makes that cardigan, but I included a very worthy substitute.

Now, with the shirt, you can either go with an Oxford button down, like I have my model wearing below or you can go with a semi-spread collar dress shirt.  if you wanted to dress it down a bit more, you can go with a white v-neck t-shirt, like Daniel Craig also wore in Casino Royale.

JamesBondCasinoRoyalCardiganSweaterVNeckTShirtAshleyWeston

Pants, Shoes & Sunglasses

As for the pants, tan or sand colored chinos are perfect here. Just please make sure that they fit properly, otherwise it won’t look so great.

In the full length image at the top of the page, you’ll see bond is wearing brown suede chukka boots, which as I mentioned in the companion video to this one on Antonio’s Real Men Real Style channel, I’m not the biggest fan because they get gross and dirty quite quickly. So instead, I’d go for something like brown oxford dress shoes. That way, you’ll keep the same general profile as the original outfit and you hopefully already have these in your closet, so it’s a perfect way to incorporate them into a more casual outfit. I find a lot of men have a problem with mixing their dress shoes into more casual outfits and this is a perfect example of when it’s appropriate to add them in.

The final piece of the puzzle is the sunglasses. Daniel Craig is wearing aviators by Tom Ford in the film, but whether you should be wearing those or another style is dependent on your face shape. Since my model has a more oval face shape, I went with squared Tom Ford wayfarer-style sunglasses instead.

My Version of this outfit

I also wanted to mix a more budget-friendly piece, like the chino pants, with less budget-friendly items, because for some reason, a lot of men think that if they’re wearing an expensive item, everything else has to be equally expensive or it just won’t look right. Well, hopefully you see that this couldn’t be further from the truth.

James-Bond-Cardigan-Quantum-of-Solace-Ashley-Weston

Rag & Bone Avery Shawl Cardigan
Brooks Brothers Red Fleece White Solid Oxford Sport Shirt
Uniqlo Mens Flat Front Slim-Fit Chino Pants
Tom Ford Black Snowdon Sunglasses
Salvatore Ferragamo Remigio Cap Toe

Designer Options

 

Brooks Brothers Shawl Collar Cardigan
Dolce & Gabbana Shawl-Collar Virgin Wool Cardigan
Brunello Cucinelli Slim-Fit Button-Down Collar Cotton Oxford Shirt
Burberry Check Detail Cotton Oxford Shirt
J Brand Brooks Slim Trouser
Burberry Slim Fit Cotton Chino
Allen Edmonds Park Ave Cap-Toe Oxfords
Christian Louboutin Greggo Balmorals
Tom Ford William Silver sunglasses

Budget Friendly options

 

Club Monaco Shawl-Collar Elbow Patch Merino Sweater
J. Crew Cotton Cardigan Sweater
Topman White Oxford Long Sleeve
J. Crew Slim Thomas Mason for J. Crew
Uniqlo Mens Flat Front Slim-Fit Chino Pants
J. Crew Broken-in Chino 770 Fit
Johnston & Murphy Melton Cap Toe
Aldo Anniex Cap Toes
Ray Ban Aviator Classic

Outfit Inspiration For Cardigans & Chinos

The #AskAW Show: Episode 03

Have a question you’d like me to answer? Ask in the comments of this youtube video or send me an email.

Show Notes & Links

Q: How should a sport coat look and fit?

How Your Suit Should Fit

 

Q: How do I dress in a more “mature” style that makes me look my age?

See my Men’s Wardrobe Essentials articles for the clothing you should be wearing to look more mature. Also, see my Men’s Clothing Fit Guide for how each of these items should fit, regardless of your age or body type.

Sportcoat

Oxford Button Down Dress Shirt

 

Dark Wash Jeans 

 

Wool Trousers

 

Oxford Dress Shoe

 

 Belts

Q: Looking to replace my worn-out wingtips with black cap-toe Oxfords or should I keep them and get Oxblood Oxfords, instead?

Oxford Shoes

 

 

The Oxford Dress Shoe

This article is part of my Men’s Wardrobe Essentials series.
These are the best mens dress shoes, no questions asked. Anything else pales in comparison. Every man should have at least 2 pairs of Oxford dress shoes in his closet. Not only are they one of the most versatile shoes a gentleman can own – which will work for nearly all formal occasions from business casual to formal – but they’re the de-facto standard shoes to wear with a suit. On top of that, they’ll also work very well with 99% of the items in your Essential Wardrobe. They’re that good.

When you imagine a well-dressed man in a suit, I guarantee he’s wearing a pair of these.

Black & Leather ≠ Oxford Dress Shoes

Don’t think that if a shoe is black and leather, it’s an Oxford dress shoe. I shudder at the thought of those square-toed and/or slip-on monstrosities I see men wearing in place of a proper, lace up, round-toed dress shoe.

Also, if you can see your reflection in your black leather shoes, those are not a proper dress shoe. Those are tuxedo shoes. As the name implies, they should only be worn with a tuxedo. I’ve seen quite a few guys wearing these shoes with jeans. It’s not a good look. Your Oxfords shouldn’t look like mirrors, they should be a little more matte finished. Go to a department store and ask to see their tuxedo shoes so you can see the difference in person.

The image below from RealMenRealStyle highlights exactly what I see a lot of men wearing in place of Oxford dress shoes:

Wrong-Square-Toe-Shoes

To Cap-Toe or Not?

My opinion about whether you should have a cap toe Oxford or not changes with the wind, so I’ll leave it up to you. There’s not a single scenario when you’d wear a cap-toe over a non-cap toe, so this is entirely up to your preference. 

My clients are split 50/50 on this, too. You won’t go wrong with either, so choose whichever you think looks great and fits your style best.

allenedmonds_shoes_carlyle_blackallenedmonds_shoes_park-avenue_black

Should I go for Quality or Value?

For foundational pieces such as these, I’d say go for quality. However, there is a caveat:

How Often Will You Be Wearing Your Oxford Dress Shoes?

  • If you’ll be wearing them more than a handful of times a month, definitely grab a nice, high quality pair. They’ll give you many good years of use and look great the whole time.
  • If you’ll be wearing them once a month or less, go for value. They’ll definitely get the job done and look “good enough”. What’s the use of having a high quality pair of dress shoes sitting in your closet most of the time? I’d take that money and spend it on other pieces you might wear more often](link).

Which Shoes Should I Get?

Since you’ve decided whether you like cap-toe or non cap-toe shoes, now it just comes down to color.

Every guy should have these two pairs of Oxfords in their wardrobe to cover every outfit choice:

  1. A solid black pair
  2. A brown/cognac pair

Anything outside of those two colors will have more specific uses and occasions and definitely falls outside the domain of an Essential Wardrobe item.

The Best Mens Dress Shoes

These are my go-to Oxfords for clients:

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

2 Ways to Wear

For other ways to wear your Oxford dress shoes, check out my Gray Notch Lapel Suit article, Dark Wash JeanSemi-Spread Collar Dress Shirt & Leather Jacket articles.

BlackOxfordDressShoeLook1640-Ashley-Weston-Mens-Wardrobe-Essentials

Model: Tommy Mckeown

Fred Perry Reissues Harrington Jacket
Brooks Brothers 3-D Knit Fine-Gauge Merino Wool Crewneck Sweater
Brooks Brothers Non-Iron Milano Fit Button-Down Collared Dress Shirt
Burberry Straight Fit Japanese Selvedge Denim Jeans
True Vintage Revival Glasses
Allen Edmonds Poplar Dress Belt
Daniel Wellington Classic Sheffield 36mm
Allen Edmonds Carlyle Plain-Toe Oxfords

BlackOxfordDressShoeLook2640-Ashley-Weston-Mens-Wardrobe-Essentials

Brooks Brothers Red Fleece Topcoat
Brooks Brothers 3-D Knit Fine-Gauge Merino Wool Crewneck Sweater
Brooks Brothers Non-Iron Milano Fit Button Down Collar Shirt
Brooks Brothers Fitzgerald Fit Wool Dress Trousers 
Allen Edmonds Poplar Dress Belt 
Daniel Wellington Classic Sheffield 36mm
Allen Edmonds Carlyle Plain-toe Oxfords

Outfit Inspiration