What Shoes to Wear with Sweatpants? (7 Options Explored)

What Shoes to Wear with Sweatpants?

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Sweatpants are the best kind of pants. You know that if you’ve ever owned a pair (or ten). They’re the most comfortable pants you can own, which is why people wear them around the house, to the gym, and even outside when it’s warm enough.

The trick to finding the right pair of shoes for your sweatpants is to select shoes that are both stylish and comfortable. You want to look good without sacrificing comfort and you don’t want to look sloppy either!

These days, there are so many styles of shoes out there that you can match your sweatpants with almost any shoe available. You can choose from a variety of types of shoes like flats or heels, boots or sneakers, and even sandals or flip-flops.

But whether you’re wearing them out of the house or just hanging around in your sweatpants, you need to make sure that you’re wearing shoes that go with them.

So what shoes do you wear with sweatpants? Here are some ideas:

Can You Wear Boots with Sweatpants?

Boots keep your legs warm and dry while giving you a polished look that works equally well at the gym or out at night.

So could you wear boots with your sweatpants? The answer is yes. You absolutely can. But not just any boot will do. You need a boot that isn’t too dressy and has some attitude to it.

Here are 5 boot styles that look fabulous with sweatpants:

  1. Chelsea Boots – These are great with pretty much any type of pants, including sweatpants. Chelsea boots don’t go too high on your leg, so if you’re not a fan of showing off your calves and ankles, these are an excellent choice! They also have a great tread on them, so you can wear them in the rain.
  2. Ankle Boots – These look great with pants that cover most of your lower leg, but leave enough room to show off your ankle. They go well with tight black jeans, as well as sweatpants or leggings. You can also roll up the leg of your pants to show off more of your ankle if you want.
  3. Riding Boots – If you want to show off more legs and are okay with it being seen, riding boots are a great option for you! They come in both knee-high and thigh-high styles.
  4. Double Buckle Boots – Double buckle booties provide extra support and they have a little bit more detail than regular ankle boots. You can wear them with skinny jeans or leggings during the winter and then transition to wearing them with your favorite pair of comfy sweatpants when the temperature rises.
  5. Lace-up combat boots –  Lace-up combat boots are such a cool, classic style that never goes out of style! The lace-up details on these make them unique, as well as the sleek black color that makes them ideal for wearing with a pair of sweatpants or leggings or they’ll just look like regular boots!

Can You Wear Sweatpants with Cowboy Boots?

Can you wear sweatpants with cowboy boots? Yes, but you need to keep a few things in mind in order to make sure that the ensemble comes off looking good and not like something your mom picked out for you when she was doing laundry.

This outfit may be frowned upon on the streets of Brooklyn, but the truth is that it’s a great look for a night out on the town. Sweatpants are comfortable and warm, but they can also look sloppy and unkempt if you’re not careful. Cowboy boots add a bit of an edge to this look, while a plaid shirt ties it together with some added country flavor.

Can You Wear Sweatpants with Timberlands?

Sweatpants are a fashion staple for many people, but it’s not often that you’ll see them paired with boots like Timberlands outside of its intended use. While the combination may seem odd at first, combining these two items is actually more complementary than you might think.

The classic Timberland boot is an iconic piece of footwear that has been around for decades and remains a staple in any man’s closet. The shoe itself is constructed of higher-quality leather that will last you many years to come, and the signature yellow stitching makes the boot instantly recognizable.

In recent years, the boot has become increasingly popular among younger people, namely because it goes with just about anything in your wardrobe.

While some may not see Timberlands as being “cool” enough to wear with sweatpants, there’s a lot to be said about the timeless style that endures beyond trends and fleeting fads.

If you’re wearing sweatpants and Timberlands together, consider pairing it with a stylish hoodie or T-shirt to complete the look. A nice pair of black socks is also something worth investing in if this look appeals to you, as black socks will help them blend in better with your shoes.

Can You Wear Sweatpants with Doc Martens?

Trying to wear Dr. Martens with sweatpants can be done, but it requires a few key pieces to really pull it off. First and foremost, you need a good pair of sweatpants that are slim fit. The tighter the better. A slim fit can help eliminate the bagginess of sweatpants, which can sometimes make them look too casual for Dr. Martens.

Dr. Martens Vegan 1460 Smooth Black Combat Boot, Fleix Rub, 7 UK/US Men's 8 Women's 9 D US

If you want to wear sweatpants with Doc Martens, make sure they are high-quality sweatpants that are slim-fitting and have a flattering color and pattern. Also, you should wear them with a black tee-shirt or top that fits well, but that isn’t too tight or short.

Can You Wear Converse with Sweatpants?

It’s summer and you’re out of school. You have a couple of weeks before you go back to work or college. It’s time to get fresh, new, and most importantly- comfortable! Your perfect outfit is sweatpants and converse sneakers. Converse are easy shoes to wear. All you need to do is slip them on and you’re out the door.

Sweatpants are comfy, sneakers are comfy, together they’re even cozier. Plus, if you’re breaking in a new pair of kicks, there’s no better way to do so than by wearing them with your favorite pair of sweats.

Here are five reasons you can wear converse with sweatpants:

  1. They keep your toes warm – If you’re not into wearing socks but still want to keep your baby-pink toes warm, slip on a pair of Converse Chuck Taylor All-Star high-tops, and the problem is solved.
  2. They make you feel like a kid again – Sneakers and sweats may be an adult clothing combo but some of us feel like it takes us back to our childhood days. We don’t know about you but we love these feelings!
  3. You can wear them everywhere – Whether you’re at the gym or grocery shopping, converse sneakers go with everything – and we mean everything! Even formal events!
  4. Comfort – Sweatpants are meant to be worn in the house and Converse are made for walking around. So why not put them both to good use? You’ll be comfortable in your own home and still look stylish enough to grab a cup of coffee or walk your dog without getting strange looks from people passing you on the street.
  5. Style – There’s no need to worry about how it looks because it’s stylish and fashionable. Just think of all the celebrities who have been caught wearing this combo. Even Kendall Jenner has been seen wearing sweatpants and Converse sneakers, so if she does it, it must be OK, right?

Can You Wear Sweatpants with Vans?

There’s a common misconception that Vans are only for skateboarding, but the truth is, they look good with just about anything. And since Vans are about as casual as sneakers get, they work with pretty much any outfit.

Here are some reasons why you should wear your Vans with sweatpants:

  • They’re comfortable – Vans are one of the most comfortable sneakers around — and it doesn’t matter whether you’re wearing them with jeans or sweatpants. In fact, Vans sneakers are so easy on your feet than wearing them with your favorite pair of sweatpants is almost like wearing slippers for the day.
  • Quality and versatility – Have you ever noticed how versatile Vans sneakers are? Whether you’re casual or a bit more dressed up, Vans will always be an excellent addition to your outfit. It’s nice to have a pair of sneakers that can be worn on any occasion — even if said occasion requires you to wear sweatpants. They go with everything.
  • They’re stylish – Although some may disagree, it’s true that Vans come in many different styles these days. You can get slip-on versions or lace-up versions depending on your preferences and needs. Regardless of what type of Vans you own, they will always look stylish and go well with a variety of outfits
  • They can help boost your confidence – You have no doubt seen people around campus wearing their Vans with sweatpants, but did you ever stop to think about why? There is nothing wrong with pairing your comfy sweats with your sneakers because it makes you feel confident. You will not only look cool but also feel cool while doing it!

Can You Wear Heels with Sweatpants?

You should start by deciding what type of shoes look good with your sweatpants. Flats and sneakers are probably the best combinations because they don’t make you look too dressed up.

On the other hand, if you’re wearing a pair of dressy sweatpants made out of silk, you might want to wear a pair of heels to tone down the outfit a bit.

Match your shoes to your outfit in terms of style as well as color. For instance, if you’re wearing gray sweats with a black skirt, try a pair of black heels. However, if you’re pairing black sweatpants with an equally dark top and jacket, something with some color might be more appropriate like red heels.


In summary, a pair of grey sweatpants with minimal detailing will perfectly match a classic white pair of converse high-tops. A simple black Vans shoe can easily be worn with uniquely colored sweatpants. And a pair of embellished cowboy boots provide the perfect addition to a casual pair of comfortable sweatpants or joggers. With so many wardrobe possibilities, you will have no trouble finding the right shoes to wear with your sweatpants.

You may also be interested in… Are Vans Comfortable? and Do Clay Courts Ruin Your Shoes?