Wondering What To Wear With Trending Ugly Sneakers?

Huge, chunky and colorful sneakers like those worn to the gym in the ’90s have been enjoying a resurgence in popularity and their appeal isn’t likely to fade any time soon. Are we crazy about them because the look is so contrarian or simply because they are so darn comfortable? Whatever the reason, you’ve got to have at least one pair of shoes that mimics your Dad’s. While they are irresistible, ugly sneakers do pose a dilemma. What to wear with them that will further enhance your hip image?

Of course you can wear them with Dad jeans. You can borrow Bella Hadid’s oversize jacket, don mini-skirts or go romantic with floral dresses. Balance the ugly sneaker with elegant pantsuits and tailored trousers or pair them with a nice striped dress and coat. Socks are the very foundation of the ugly sneaker look and mercifully, the natural choice is the geeky white sock that’s the pride of any nerd.

How did they become popular?

The current wave can be traced to the Céline sneakers that designer Phoebe Philo presented in her Spring 2013 collection. Soon after that, ugly sneakers started showing up on catwalks and the streets of NYC and LA and other fashion centers: London, Paris, Milan.

Ugly shoes been seen on sisters Kim Kardashian and Kendall Jenner, Bella Hadid, Hailey Baldwin and Jaden Smith. Popularity may have reached its height when Balenciaga’s chunky platform Crocs priced at $850 sold out even before their official release.

Ideally, the ugly sneaker should be an in-your-face attention grabber that throws your outfit slightly out of kilter. Here’s what to wear to make the most of the big, bulky, bold shoe.


Choosing the right sock is important for your total look when you’re wearing the ugly sneaker. White nerd socks are a match made in heaven for clunky footwear and they go with just about any nerd sneaker.

Save your cool patterned socks for Dad sneakers in white, black or other solid colors. A simple polka dot or stripe, or a plain color with a pattern would look good. If your sneakers are colorful, pair them with scrunched white socks or solid color socks.

Cropped socks and mid-length socks work with ugly sneakers, and you can also wear tights.

Here are styles of jeans and pants that wear well with these ugly sneakers.

Heavier shoes

Cropped vintage Levi’s would look cool with heavier ugly sneakers because these jeans bare the ankle. Pants that aren’t cropped at the ankle will puddle into your ugly sneakers and you’ll lose all cool. Also look for a wide leg crop utility pant to wear with heavier shoes. Emphasis is on baring the ankle.

Pointy toe and straight sole

Shoes with a pointier toe and straight sole such as the Nike Air Max 97 Ultra ‘17 SE Sneaker go well with slightly flared or subtly kick-flared, straight legged pants. Make sure the pants reveal the ankle and steer clear of pants that are too reminiscent of the ‘70s. The cropped pant has got to stop short of the ankle.

Funky, jagged-soled sneakers

Slim white pants are fitted enough to balance the bulkiness of ugly sneakers. Did I mention that they should be cropped above the ankle?

Slim-profile ugly sneakers

High-waisted and wide-legged pants make a great partner for the slimmer Dad sneaker.

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