The Best Dress Shoes For Men Are Always Formal, Yet Fun

These are no exception

BY: Beau Hayhoe
Update: May 8, 2024

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There are certain areas in a menswear wardrobe where you simply can’t cut corners, starting from the ground up. In fact, I meant that literally: If you’re stepping out in subpar shoes for dressy style situations, you’re going to feel it, both in matters of comfort and style. And there are certainly no shortage of style scenarios where the best dress shoes for men come in handy.

The best men’s dress shoes are a statement all their own, a complement to your everyday office looks (like stretch chinos and a navy polo) as well as elegant affairs (like a seasonal wedding).

The right pair can exude confidence and style, and I look to a handful of trusted brands to jazz up my wardrobe accordingly. Some are made with sneaker-like technology or eye-catching details like wingtip detailing, some pair best with chinos rather than a suit, but all are here just in the nick of time – the next time you really need to dress up, that is.

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COMFORT

Are your dress shoes going to be as comfortable as your favorite pair of sneakers? Hardly. Might there be some break-in time required with more expensive pairs? Surely. But when all is said and done, it’s possible nowadays to find a pair of the best men’s dress shoes that just so happen to be crafted with quality materials and comfort in mind, from the outsole to the midsole to arch support – these qualities were top of mind.

STYLE

What sort of dress shoes do you need? Are you in the market for a wear-with-anything dark brown pair or a pair of ultra-formal black dress shoes you can wear for years at a time? Either way, great looks – from details like a wingtip design to the actual shape of the shoe itself – are a must-have among the best men’s dress shoes. Most of the best pairs work well with everything from tobacco-hued chinos to a navy suit.

VALUE

Value isn’t quite the same thing as affordability. While it’d be ideal if every pair of dress shoes didn’t cost you an arm and a leg, this is sometimes an area where splurging a slight amount (you’ll recognize the brands in question) can pay off. If you’re wearing dress shoes every single day, and in many of the same scenarios – for example, black dress shoes with dark pants – then a pricier pair makes perfect sense. So, value is the name of the game, rather than skimping with a super budget-friendly pair.

OUR BEST DRESS SHOE WINNERS

Florsheim Rucci Cap Toe Oxfords

best formal shoes overall

PROS

CONS

Clean, crisp black dress shoes are a must in every guy’s footwear selection of the best men’s dress shoes. They’re an absolute must with a black suit, they even wear well with navy suiting and they’re helpful to have on hand for weddings and funerals. That’s a lot of mileage being put on one pair of shoes, right?

Accordingly, Florsheim crafts a quality pair that doesn’t cost an arm and a leg, although designer brands also offer significantly more expensive black dress shoes – if that’s your bag. These do feature a slightly more casual captoe design, but don’t stray away from wearing them with a suit (Take it from me, as I’ve tried out this style in the past).

SPECS:

Thursday Boots Executive Dress Shoes in Chestnut

high quality at reasonable price

PROS

CONS

The best way to start your search for, well, a pair of the best dress shoes for men? Keep it relatively simple by shopping a boot brand you know and trust. Thursday Boots uses rich craftsmanship and handsome leathers in every pair, especially this highly wearable shade of Chestnut.

That’s not all: Closed lacing makes for a streamlined, sleek shoe, while a captoe finish makes these both casual enough to wear with chinos and formal enough to wear with a suit (in plenty of different shades, mind you). And at under $200, these are fairly priced – a Goodyear welt construction also means they can be resoled for added longevity.

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Cole Haan American Classics Montrose Plain Toe Oxfords

best suede option

PROS

CONS

Don’t sleep on the style of suede in your rotation of the best dress shoes for men, especially as you search for a pair through the spring and summer (and fall) months.

Cole Haan blends a tried-and-true, plain toe Oxford look with rich suede and its sneaker-like comfort – all are major bonuses for your footwear of choice. The tan suede goes with just about anything in your wardrobe, from navy chinos to olive linen trousers. Better still is the molded EVA footbed and lightweight EVA outsole – that means hours of comfort on your feet, whether at business meetings or cutting a rug on the dance floor.

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Allen Edmonds McAllister Wingtip Oxfords

best investment shoe

PROS

CONS

You might call Allen Edmonds the “creme de la creme” when it comes to the best men’s dress shoes out there, at least in terms of legacy and long-lasting durability. Oh, and style points, too.

The iconic American company has been a mainstay in the dress shoe market for decades, with timeless styles that exude confidence and taste. Its handsome wingtip Oxford dress shoes are a perfect anchor to more traditional styles (the light grey suit) as well as seasonal looks (like a navy seersucker suit).

And with dark tan chinos, an Oxford shirt and a lightweight navy blazer, they’re practically a requirement. Remember the fact that I mentioned you can splurge on dress shoes from time to time? This is a pair that’s worthy of an investment.

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Nordstrom Dax Plain Toe Derby Shoes

best budget-friendly shoe

PROS

CONS

There are certainly plenty of ornate styles out there when it comes to the best men’s dress shoes, but from time to time, simplicity and subtle style work nicely. Such is the case with a pair of dark brown dress shoes, which I’ve found are about as reliable as it gets for a 9-to-5 grind and beyond.

And since Nordstrom has been diving into its own namesake menswear line in recent years, that makes it easier than ever to get an affordable, well-made pair of shoes (and an accompanying dress shirt and sweater, for example). These plain-toe derby shoes are your daily workhorse, and then some, and they go for a steal of a deal when on sale.

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EDITORIAL PICKS BY CATEGORY

Looking for our picks based on a specific style of shoe? Some of our editors here at Brostrick chose their favorites. Check these out. The following editors contributed:

Editor: Patrick Varone
Editor: Jennifer Belanger
Digital Designer: Ethan Easton

OXFORD SHOES

The quintessential dress shoe, the Oxford is defined by its clean lines and minimalistic design. The hallmark feature is the closed lacing system, which provides a snug fit and a streamlined silhouette. The vamp is stitched over the eyelet tabs, offering a sleek appearance that enhances its formality.

Oxfords can come in various finishes, including patent leather for formal occasions and more textured leathers for everyday wear.

With Oxfords, you can traditionally pair them with formal business attire, like a perfectly tailored suit and even dress pants. They’re usually the best choice for high-stake business meetings, formal ceremonies, and any event where a sharp, polished appearance is a must.

Allen Edmonds

Strand Cap-Toe Oxford Dress Shoe

Florsheim

Kenmore Wingtip Oxford

Bruno Magli

Cap-Toe Oxford

DERBY SHOES

One of our personal favorites, Derby shoes typically feature an open lacing system, where the eyelet facings are sewn on top of the vamp. This design allows for a wider opening and a more comfortable fit, especially for those with high arches. While they look similar to Oxfords, the visible lacing of the Derby lends a slightly less formal tone, making it versatile for a wide for occasions.

Speaking of which, we find Derby shoes perfect for both smart-casual and semi-formal outfits. Derbies can be easily styled with everything from suits to casual denim (except jeans with rips or holes), making them a reliable choice for everyday office wear or casually fun meetups.

Christian Louboutin

Urbino Leather Derby Shoe

Allen Edmonds

Park Avenue Derby

Thomas & Vine

Fremont Derby Shoes

MONK STRAP SHOES

Not all guys are totally comfortable wearing these, but monk strap shoes feature a buckle and strap instead of laces, combining the slip-on appeal of loafers with a more secured fit. The buckle detail can range from understated to bold, offering a unique style point that catches the eye. They’re available in single or double-buckled styles, each adding a different level of flair depending on how far you want to go.

As far as how and where to sport these, monk straps can really adapt to a many different settings, from the traditional conservative office o more relaxed social events. They work exceptionally well with tailored trousers and sports coats, bridging the gap between formal and casual with ease.

Florsheim

Ravello Monk Strap Shoe

Mr. P

Double Monk Strap Patent Leather

Allen Edmonds

St. John's Double Monk Strap

LOAFERS

From classic and dressy to more casual and comfortable loafers are slip-on shoes that forego laces for a seamless upper, contributing to their easy-going nature. They come in so many different styles like the most famous penny loafer with a leather strap across the top, and the more decorated tassel loafer. Their ease of wear and comfortable design make them a favorite for most guys.

If you’re going the classic penny loafers route, they’re perfectly paired with your favorite chinos and a blazer or even with suits in more relaxed business settings. If you’re into tassel loafers, those skew a bit more flamboyant and fit well with smart-casual outfits.

Todd Snyder

Boston Penny Loafer

Allen Edmonds

Randolph Bit Loafers

Clarks

Whiddon Step Loafer

Beau Hayhoe

Welcome Beau, our Men's Style & Grooming Editor here at Brostrick. A journalism grad from Michigan State University and current Brooklyn resident, Beau has been covering all things guys are into for publishers like Maxim Magazine, Esquire, Men's Journal, Fatherly, Business Insider, Gear Patrol, The Robb Report and more.

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