Ask a Fashion Editor: What Kind of Shoes Should I Wear with Sweatpants?

Dear Fashion Editor,

I’m not ashamed to admit that I wear sweatpants all the time. Like, from the second I wake up to the minute I go to bed, I’m wearing these cozy pants. OK, I also wear them while I’m sleeping. The only issue? I have no clue what kind of shoes to wear with them when I have to leave the house. Are sneakers the only option? Or are boots OK? Nothing that I pair with my sweats looks right. Help!

From,
Seriously Confused But Comfy

Hi there SCBC,

I’m going to go ahead and say it: You speak for us all with this question. And I’m not going to lie, it stumped me for a bit. Because I couldn’t, in good conscience, tell you to put on any ol’ pair of comfortable sneakers with your go-to sweats and call it a day.

But after doing a bit of Instagram stalking (after which I can confirm Hailey Bieber is the queen of making sweats look unbelievably cool) and some masked street stalking, too (I only got a few weird looks), I discovered one common thread among the cute looks. It’s all about highlighting the ankle! It sounds simple, but there’s something about a flash of skin (or sock) at the bottom of a loose, casual pant that makes this piece of loungewear feel more like a cool streetwear look and less like something tossed together from the dirty laundry pile.

However, it’s worth noting that this advice works with a pant that’s cinched at the ankle—and doubly so if said pant is slightly cropped to or right above the ankle. This ensures there’s no mess of fabric pooling above the shoe, creating a slightly more streamlined effect while offering plenty of opportunities for bypassers to peep at your purposely exposed ankle.

This leads us to the number-one most flattering kick to wear: the semi-clunky, vintage-inspired sneaker. Not quite a dad sneak, these are more of the technical kicks that are akin to a New Balance 990v5 ($175) or even the thick-soled Nike Air Force 1s ($110). To really maximize the effect and, make you look like Mrs. Beiber, you’ll want to acquire a pair of white tube socks ($15). Not into a statement sock? Try a retro-chic high-top sneaker, like the Reebok Lifestyle F/S Hi ($70) which will most definitely do the job of drawing attention to your lovely ankles.

Another clunky shoe option (that’s pretty in for 2021) is a shorter combat boot. We’re talking a lace-up that ends right above the ankle bone and is finished off with a healthy lug-sole detail. This adds an edgy touch to your sweats, highlights the slimmest part of your leg and offers a little weatherproofing if you’re venturing out into the cold. Finally, if you’re looking to go the dressy route (the best way to wear sweats when you have a dinner reservation), I’d suggest reaching for your pointiest heels. These can be kitten heel mules or a classic pump with a six-inch stiletto, but you’ll want to be working with sharp point. Why does that work? Well, similar to the clunky-ish sneaker, it plays up a healthy juxtaposition. But this time it's between soft sweats and sexy shoes.

Now that we’ve got that down, let’s go over the shoes you shouldn’t wear. I’d suggest refraining from rocking your ankle booties or anything that looks too polished, especially if it has a heel, since it just doesn’t provide the right contrast between of high/low. Nor does it look particularly right. (It’s one of those ‘when you see it, you get it’ situations.) I’d also recommend staying far away from any shoe that climbs two inches above the ankle. You should also leave some of the more streamlined or slimmer silhouette sneakers behind, since, as we mentioned, sweats do look nicely balanced when worn with a chunkier sole.

And, because I know you want to see them, here are three sweatpant outfits that perfectly demonstrate my tips.