A Guide to Casual Shoes That Aren't Sneakers

Believe it or not, sneakers will only take you so far in life.

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Complex Original

Image via Complex Original

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You’ve amassed quite the sneaker collection over the years. You have a fresh pair for every day of the week—something to go along with every ‘fit in your wardrobe. As soon as a new pair of J’s come out, you’re first in line to cop and add them to your larger-than-life sneaker rotation (by any means necessary). And we get it: sneakers are aesthetically appealing, are pretty versatile, and are good for the street cred. However, as coveted as they may be, the reality is that sneakers will only take you so far in life. For you sneakerheads, that’s probably not something that you want to hear, but it is what it is. 

It’s said that you can tell a lot about a man just by the type of shoes that he wears. Well we’re taking that one step further to say that shoes are the most important part of a man's wardrobe. With that in mind, it's time to add some depth to your casual footwear game this summer. To help your cause, we’ve put together the following guide to casual shoes that aren't sneakers, complete with some solid options for you to choose from.

Penny Loafers

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What used to be referred to as the “official shoe” of preps worldwide is now street-style approved for all guys to rock—not just bros in polos. This type of loafer features a leather strap across the top, complete with a slit (often in the shape of a diamond) big enough to hold a coin (hence the name). It’s a simple style that is the epitome of versatility; penny loafers can be worn to summer weddings, while running errands around the city, and every other casual summer occasion in between. That versatility extends across all pant types too—from jeans, chinos, casual suits (do those even exist anymore?), and more.

Tan Leather Penny Loafers

Buy now for $90 at Topman

Paul Smith Casey Suede Loafers

Buy now for $299 at Coggles

Hitch Penny Burgundy Suede Loafers

Buy now for $60 at Topman

Tassel Loafers

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A style that you’d probably expect to see on your Ivy League granddad’s feet, the tassel loafer has been resurrected to become a footwear staple in the casual menswear shoe game. It’s essentially a standard loafer, meaning a laceless, low-cut shoe with a separate sole—just with the addition of a tassel that hangs off the tongue. This type of shoe is made for the summer, so whether you’re hitting up a barbecue or a casual night out, you’re good to go. For best results, remember to pair your tassel loafers with some fitted pants (shorts are acceptable as well, if you must) and ditch the socks.​

Asos Tassel Leather Loafers

Buy now for $73 at Asos

Black Leather Pine Reptile Loafers

Buy now for $90 at Topman

House of Hounds Navy Suede Tassel Loafers

Buy now for $110 at Topman


Desert Boots

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Desert boots—an offshoot of the chukka—have become one of the more popular boot styles in recent menswear history. A lightweight construction and all-day comfort may have something to do with that. It’s a versatile shoe type that can be worn three out of the four seasons, adding the perfect element of smart casual to your wardrobe. A simple, everyday shoe with lots of color options, the desert boot will never go out of style, and it has the potential to quickly becoming your go-to shoes for daily wear.

Wolverine 1883 Orville Suede Desert Boot

Buy now for $95 at Amazon

Clarks Originals Nubuck Desert Boots

Buy now for $179 at Asos

H by Hudson Cruise Desert Boots

Buy now for $255 at Amazon


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The versatility of a shoe goes right out the window if it doesn’t look good. Fortunately, the chukka delivers on both fronts with a minimalist design that can be dressed up or down to coincide with any casual outfit. A shoe that has roots on the polo ground has become a footwear classic that has withstood the test of time. 

Loake 1880 Kempton Chukka

Buy now for $360 at East Dane

The Generic Man Quilted Leather Chukka

Buy now for $99 at East Dane


Frank Wright Strachan Chukka Boots

Buy now for $154 at Asos

Oxford Shoes

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The oxford may be a dress shoe by definition, but you may as well throw out rule book because the popularity of the shoe style from a historical perspective has propelled it from the prep school campus to the forefront of casual footwear in recent times. The British-inspired design has been reimagined as an American staple that works on many levels. Contrary to popular misconception, every lace-up shoe is NOT an oxford. Unlike a Derby shoe, which is almost identical except for its open front, the oxford stands out for its closed lacing system—a feature that lends itself nicely to clean, minimalist wear.

Carlin Brogue Burgundy Oxford Brogues

Buy now for $80 at Topman

Ted Baker Luhwice Suede Oxfords

Buy now for $199 at Asos

Cole Haan Cambridge Cap Toe Oxfords

Buy now for $258 at Amazon

Derby Shoes

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To the untrained eye, the Derby has “dress shoe” written all over it. But don’t let that basic thought process fool you into believing that these aren’t worthy of your next street-style photo-op. Throw these on with a pair of tapered or rolled-up pants and you’ll see what we mean. (The style is similar to oxford shoes except with an open-faced lacing system).

H by Hudson Hadstone Derby Shoes

Buy now for $160 at Amazon

Black Leather Derby Shoes

Buy now for $130 at Topman

Rockport Refinement Plain Toe

Buy now for $160 at Amazon

Chelsea Boots

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This is a style of shoe that has become synonymous with artists and rock starts (namely The Beatles). The Chelsea boot, with its heritage-inspired look, adds dimension to a man’s wardrobe, with its sleek, clean lines lending themselves nicely to the fitted attire that is so prevalent in menswear today. It’s an old school shoe with new school swag.

Dr Martens Original Chelsea Boots

Buy now for $130 at Asos

Wolverine 1883 Garrick Chelsea Boots

Buy now for $165 at Amazon

Base London Combust Leather Chelsea Boots

Buy now for $135 at Asos


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We don’t recommend you wearing sandals and/or slip-ons on the daily. In fact, we insist that you don’t. BUT, there will be times this summer when a nice pair of Birkenstocks or slip-on boat shoes will come in handy. Whether you’re heading out to the park for a booze-filled picnic or hitting the beach, this is your solution to staying casually stylish without having to get sand in your clean sneakers.

Birkenstock Soft Arizona Sandals

Buy now for $120 at Amazon

Flossy Grey Jersey Plimsolls

Buy now for $40 at Topman

Sperry Top-Sider Classic Boat Shoes

Buy now for $88 at Amazon

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