So, You Bought Baggy Jeans. Now What Shoes Do You Wear?

The other day, a 35-year-old man asked me what kind of shoes he was supposed to be wearing with his baggy jeans. The sentiment he expressed was that although he knew baggy jeans were the trendy choice of the 2020s (thank goodness we’ve left our skinny jeans behind), when it came to styling them, he was at a loss. The footwear he was wearing with his straight-leg jeans just didn’t translate right to the wider, baggier pants.

It’s true that with baggy jeans your styling is going to be a little bit different from what it would be with a slimmer fit. For one, you’re working with a wider silhouette, so you’re already losing some shape in your fit. Plus, baggy jeans, in my experience, usually mean longer jeans. With more of a break in your pants and less shoe exposed, the shoes you might usually wear with jeans can look a little bit off.

Fear not, friends! I congratulate you on embracing the baggy jeans, and I’m here to guide you through how to wear them—specifically, how to wear shoes with them. In my books, there are three types of shoes that’ll work best with your baggy jeans: sneakers, boots, and anything with a pointed toe. (Timothée Chalamet, who it seems has recently embraced the baggy jean wholeheartedly, has experimented with all of the footwear in question, so you’ll see him a few times below. Thanks, Timmy.) It’s all about creating some semblance of a good flow between your jeans and your shoes, and these are the best ways to do it.

When I was scouring the Internet to see what questions people had about the appropriate footwear for baggy jeans, by far the most common shoe people advocated for were Nike AF1’s. Now, in my books, AF1’s are shoes of the past. We left those behind in, like, 2o20. But the idea persists: With baggy jeans, sneakers are a great choice, especially sneakers with a bit of bulk to them. I’m not saying to go out and buy a super-chunky pair of kicks, but opting for a regular sneaker that has a little bit of height to it will serve you well. Pretty much anything above a Chuck Taylor is a good rule of thumb for making sure your jeans aren’t eating up your shoes and dragging on the ground.

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Boots and baggy jeans are a match made in heaven. Doesn’t matter if we’re talking about Chelsea boots or Timberlands; the shapes just work together. Baggy jeans are casual as it is, and pairing them with sneakers can amplify that effect. But opting for boots is a great way to elevate your look. Plus, most boots have a slight heel or platform, which gives you a literal boost and prevents the jeans from wearing you instead of the other way around.

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A shoe with a pointed toe does wonders in creating some dimension and shape for your baggy jeans look. Whether you’re opting for cowboy boots or Chelsea boots, giving all the bagginess of your pants somewhere to sharpen and taper makes your whole silhouette a little bit more refined. Plus, with baggy jeans, usually the toe of your shoe is going to be the only part that shows. A round toe might look good, but a pointed toe sticking out from beneath your hem will look even cooler.

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I really, really hate to be the bearer of bad news, but slim sneakers with baggy jeans tend to have a shortening effect on your frame. The combination of swaths of denim enveloping most of your shoe’s sole, by nature of it being flat, doesn’t really offer much in terms of creating height or shape. *But! There are ways you can work around this if you really, really want to wear your Adidas Sambas or Gazelles or Onitsuka Tigers with some baggy jeans, because they can offer a cool streetwear vibe.

If you’re pairing baggy jeans with slim sneakers, go for a cropped pair of jeans. Create a break between the hem of your pants and the top of your shoe, as Paul Mescal exhibits in the picture above. Showing even an inch of ankle will subtly add some height back to your frame, and the shoe won’t get swallowed up by the bagginess of your pants, either.

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