The 8 Types Of Shoes Every Man Should Own in 2021

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by  Dean Stephens | Last Updated:  Mar 23, 2021

Put away the flip flops and Crocs, boys.

You’re a man, and you shouldn’t settle for anything but the best.

We put together a list of the essential shoes that every man should own.

From high quality sneakers to a killer pair of boots, come see how many of these shoes you can check off the list.

Must-Own Men’s Shoe Styles

1. The Chelsea Boot

profile view of mgemi dritto leather chelsea boot

The Chelsea boot is the perfect representation of casual meets corporate. Falling somewhere between boots and dress shoes, they’re an awesome way to modernize your style.

Choose leather Chelsea boots for smart occasions, pointed for Friday Night drinks, and suede for casual (most popular and highly versatile).

The editorial team here at TAM waxes poetic on Chelseas so we really struggled to limit ourselves to just two picks. Forgive our enthusiasm.

Our Top Pick
Ace Marks Troy Chelsea Boot

The Ace Marks Troy Chelsea Boot is made with premium Italian calf-skin leather and a Blake stitched construction. It's lightweight, creamy-smooth, and has a stunning profile.

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Best on a Budget
Thursday Boot Company Cavalier

This dressy option pairs well with suits. There's no pull tab, so no worries about your pants getting caught in the back, which is a big problem when wearing your fancy pants. Decked out with cork-bed midsoles, the Cavalier gets more comfortable over time.

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2. The Dress Sneaker

Model Adjusting Oliver Cabell Low 1 sneaker

Everyone needs a pair of kicks with a casual vibe that still uphold a clean sense of style.

A simple pair of sneakers goes well with just about any outfit. Pick up one of our top picks and have fun wearing them with jeans, shorts, chinos, or even parachute pants. OK, maybe not parachute pants. But everything else is game.

Our Top Pick
M. Gemi The Lucente
(Get $50 off your first order with code FIRST50)

The M. Gemi Lucente is a minimalist, rich-looking dress sneaker that punches above its price-point. Its calfskin uppers and Marche construction are premium qualities usually only found in more expensive sneakers.

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Best on a Budget
New Republic Kurt

This minimalist dress sneaker is an effective weekday-into-weekend shoe thanks to its cushy insole. Go for the New Republic Kurt if out-of-the-box comfort and affordability are your priorities.

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Best in Black
Oliver Cabell Low 1
(Get $10 off with code THEADULTMAN10)

The Low 1 is Oliver Cabell's most popular shoe. It boasts a classic low-profile silhouette, with color options that are expressive, but not overly trendy or unprofessional.

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3. The Trainer

model sitting on concrete step with asket chino everlane tread white sneaker and vincero apex watch

Sometimes you need a shoe that’s easy to slip on and jet out the door. This is the kind of shoe you use to power through the tough days.

Of course, you don’t need to keep these sneaks relegated to the world of errands—paired with some joggers, trainers can be the base of an amazing laid-back casual Saturday outfit, too.

While the category “trainers” can also technically refer to any running or exercise shoes, we’re going to stick to the fashion side of things. Specialized footwear for sports is a whole different game, and not something we’re going to cover here.

Our Top Pick
Everlane Court Sneaker

Made with 93% recycled plastic and rubber and excellent quality leather from one of the worlds most sustainable tanneries in Vietnam, this sleek sneaker doesn't just look good. It is good.

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Best on a Budget
Reebok Cross Trainer

You can also find the Reebok Cross Trainer in black, but there's something special about the white leather with gum sole combo. These sneaks are lightweight, comfortable, and easy to put on miles with.

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4. The Chukka Boot

Model wearing jack mason watch and clarks desert boot adjusting pant cuff

Chukka boots are simply designed and can range anywhere from supremely casual to dressy and formal.

When deciding which chukka you’re going to get, take a quick assessment of what your wardrobe needs.

If you work in a business-casual setting, then a more formal, sleek chukka is your best bet.

But if you want comfort over all else, and formality and structure isn’t as important, a desert-campaign-style WWII-era boot like the Clarks Desert Boot is more in order.

Our Top Casual Pick
Clarks Desert Boot

The Clarks Desert Boot is over 70 years old. It wouldn't last that long if there wasn't something special about it.

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Our Top Dressy Pick
Thursday Boot Company Scout Chukka Boot

The Scout is on the dressier side of things, but you can always wear these casually, too. We like to pair them with slim jeans, but these can go with a suit, no problem.

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5. The Oxford

teal and navy polka dot sock rolled into leather oxford shoe

Oxfords are characterized by their low heel and closed lacing system. And it’s the latter this that gives them that oh-so-peculiar yet classy look.

They come in multiple variations and they’re perfect for office wear, black tie (the less detailed versions), and smart-casual events. The Oxford should be your go-to whenever you need to look respectable.

And their versatility makes them a no-brainer inclusion on this list.

Our Top Pick
Johnston & Murphy Conard Cap Toe

While I have a few gripes about the rubber outsole and the support, dollar for dollar, J&M's Conard is one of the best value for money dress shoes you’ll find in the sub $200 range.

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Best on a Budget
Florsheim Comfortech Cap Toe Oxford

This Oxford is a nice comfort-first choice for office-goers. While we'd typically step up the quality for more formal occasions, this Florsheim is a solid bet for commuters.

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6. The Service Boot

Model in woods wearing Thursday Captain

Want to look like a tough guy? Of course you do. Service boots are a little old-fashioned looking because they’re based on military boots used by service members (hence the name, service boots).

But just because they’re old-fashioned looking doesn’t mean they’re out of style. Far from it: these types of boots are all the rage right now, and here are the best of the best.

Our Top Pick
Thursday Boot Company Captain

The Thursday Boots Captain is an excellent deal. Made with Horween leather tanned in Chicago, these boots still look great after four years. When (if?) these ever wear out, I’ll be picking them up again.

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Best Premium Pick
Red Wing Heritage Iron Ranger

The Red Wing Iron Ranger is built with the heart of America. Not literally, though. These are based on a design from iron miners and they're beefy, tough, rugged and handsome.

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7. The Loafer

Volo Due on Park Bench Legs Crossed

Loafers are the signature slip-on shoes of adulthood.

They’re a solid mix of high-end style, with that low-key desire to have a fun time.

Once the kingpin shoe of the 1950’s, and now, the newest addition to your walk-in.

Our Top Pick
M.Gemi Volo Due
(Get $50 off your first order with code FIRST50)

You can't go wrong with a quality, stylish penny loafer. And that's exactly what M.Gemi have created with the Volo Due. With their streamlined and sleek design, Blake stitching, and long penny strap, we're big fans of these as more dressed up counterparts to our Saccas.

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Best on a Budget
Johnston & Murphy Breland Kiltie Tassel Loafer

If you’re looking for a slick pair of shoes to complete your outfit, save a little cash for your date and check out the Johnston & Murphy Breland Kiltie. They’re a great option for anyone not looking to dive too deep into the labyrinth that is men’s formal footwear.

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Best American Style
Jay Butler Millbank Bit Loafer

Ever tried a pair of suede loafers in the winter? There's something so sophisticated about a richly textured, glove-leather lined shoe when the temperature drops.

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And if the penny loafer is a little too simple for you, you can always add a touch of flair with the classic horse bit loafer.

Best Horsebit Loafer
Idrese Andre Horse Bit Loafer

Idrese handmakes their shoes in Spain, and it's hard to find better quality than this. Made with a 360-degree Goodyear welt, these loafers shine with an Italian wide-lapel suit.

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Based on Aldo Gucci’s famous design, horse bit loafers add a touch of sophistication and Italian gusto to an otherwise simple design.

8. The Dress Boot

closeup beckett simonon douglas jodhpur boot

Dress boots are a little less common, but when you’ve got a pair in your closet, they can easily help you look like the best-dressed guy in the room at the next wedding you go to. Not that you want to outshine the groom, but you definitely will.

Dress boots add a little more height, keep you in comfort by wrapping your ankles, and often provide more insulation than standard dress shoes.

Our Top Pick
Beckett Simonon Elliot Balmoral Boot

A Balmoral boot is essentially the boot version of an Oxford. With closed eyelets, this boot is a sleek stunner, and Beckett Simonon is one of the best values you can find on the market today.

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Best on a Budget
Thursday Boot Company President

Thursday Boot Co's Lace-Up Presidents make a prominent statement about who you are and what you're about. Leather build, rubber sole, they're made from all the right stuff. But they also offer some of the best arch support going. This one snagged our editor’s choice.

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Further Reading: How to Lace Boots Like a Pro: 6 Expert Ways

What Did We Learn?

Wearing proper kicks to an occasion slip you into an ironclad sense of confidence. It paints you as a prophet of sensible male style.

model walking with green suit and black shirt and ace marks black chelsea boots
Chelsea Boots: Ace Marks Troy

If your walk-in doesn’t have at least half-a-dozen pairs of shoes on the rack, it’s probably time to slowly invest in building it out.

thursday captain on train tracks 1
Service Boots: Thursday Captain

Your overall style and ability to be versatile with your wardrobe will dramatically increase with each style of shoes you introduce to your collection.

Model wearing olivers passage pant and oliver cabll low 1 minimalist sneakers
Dress Sneakers: Oliver Cabell Low 1

But the right shoes are just the start.

Breland Kiltie Tassel loafer sitting on steps
Tassel Loafers: Johnston & Murphy Breland Kiltie

You’ll find current attractive hairstyles, fashion guides, and dress code rules of thumb to live by, all right here. We set high standards for all fashion and grooming products that we suggest, because your trust in the quality of our content is the most important thing to us.

Do you think we blanked out on a whole category of shoes? Let us know in the comments. And be sure to follow us on Pinterest to keep track of all of our ideas.

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Bespoke Post Weekender
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Quality, affordable Creed Aventus clone
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