How to Style (Ugly) Sneakers

Lately, my footwear options have been super restricted because of an injury to my right foot. As I mentioned last month, my podiatrist told me to wear a certain ugly sneaker to give my foot room to heal. Resigned to this fate, I’ve been figuring out how to style these ugly sneakers for the past month. So, today I’m sharing some outfits.

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By the way, I put ugly in parenthesis in the title because while I was personally styling sneakers I consider ugly, you can style cute sneakers this way too. I would totally wear all the outfits below with my more attractive Everlane trainers. (You can read my review about them here.)

The Ugly Sneaker

This sneaker is actually a running shoe with lots of cushioning — so much cushioning that the bottom of it looks kind of like an inflatable boat. Opinions differ as to whether these are in fact ugly. When my sister first saw them, she asked, a bit aghast, “What are those?” The mister thinks they’re not too bad and that it’s all about your attitude when wearing them. (I think it’s a bit of both. They are ugly (not even ugly-cute), and yes, attitude counts for something.) He pointed out that he’s seen lots of young women wearing chunky sneakers on purpose — a trend from 2018 that continued into this year. Designer brands flaunted hideous sneakers on the runways. I don’t know if this makes it better or worse. It’s trendy so I won’t look so out of place? But also, I’m not doing this because it’s trendy. I’m doing it because my foot is fucked up.

Being running shoes, these come in lots of loud colorways like bright pink with blue accents and aqua blue with yellow. The first thing I did to mitigate the ugliness was to choose the all black colorway. As my every day shoes, they needed to go with as much as possible.

Look 1 – White Tee + Black Maxi Skirt

This maxi skirt is so long it nearly hides these sneakers. Plus, the black skirt with the black sneakers creates one uninterrupted stretch of black, making me look a little taller. I paired this with a simple boatneck T-shirt and a black leather tote. I ran errands in this comfy outfit on a warm day. It’s not fussy and the clean, minimalist aesthetic feels modern.

Look 2 – Striped Dress + Chambray

This is one of my usual weekend outfits (as you can see in my review of the dress). Layering is key in the San Francisco Bay Area and I often throw a relaxed button-up shirt over my outfit and tie it in the front. I like tying it at a cropped length to create the illusion of longer legs. I just subbed in these sneakers in place of my usual shoe options and while not as cute, it worked just fine.

Look 3 – Graphic Tee + Chinos

Here’s another outfit for warmer days. The chinos are comfy and the shibori print tee draws attention upward. Everything’s in the same color (yes, I wear a lot of black) so it looks pulled together even though it’s quite casual. Tucking in the T-shirt also helps it from feeling too casual. I wore this outfit often this month while I was staying in a warmer part of the country.

Look 4 – Graphic Sweater + Skinny Jeans

This is the colder weather version of the graphic tee outfit above. I swapped the T-shirt for a sweater and the lightweight chinos for thicker skinny jeans. Now that I’m looking at this, the sneakers seem even chunkier-looking to me. I think that’s because the outfit is fitted throughout. Perhaps this outfit would be better with an oversized sweater. Or maybe I should have really committed to the look and worn mom jeans instead.

Look 5 – Floral Blouse + High-Waisted Jeans

Taking the draw-attention-upward concept even further, I tucked this floral silk blouse into high-waisted jeans. The pops of orange in the marigold print were great at diverting attention from the sneakers. I liked pairing the feminine, flowy blouse with denim. It felt polished in spite of the sneakers. I wore this outfit to an event and dinner with friends.

Look 6 – Sweats + Moto Jacket

Here’s an outfit I wore on a cooler day. I started with my favorite graphic sweatshirt, paired it with sweatpants, then threw on a moto jacket. I love moto jackets. They bring a bit of edge and instantly make any outfit feel more stylish. The sweatpants I’m wearing are on the slimmer side, which keeps the outfit from looking too sweats-like.

During the past month, I’ve played with variations on these looks. And of course, I’m an outfit repeater, so some of these looks I wore a lot. Hope this post has brought you a few helpful ideas! How would you wear ugly sneakers?

UPDATE 11/23/19 – I just found these sneakers on Opening Ceremony’s site and am tickled. They even collaborated to make their own sneaker for the store. More proof that ugly sneakers are in.