How to Wear Boxers With Jeans

Trying to get your underwear to cooperate when you slide on your favorite pair of jeans is always a little harder than most expect.

For starters, boxers are generally pretty “loosey-goosey” kind of underwear to begin with.

Super casual, super laid-back, and super comfortable (for the most part), the only trick with boxers is getting them to stay in place when you tug on a pair of jeans.

As soon as the denim hits they start to go crazy, riding up, slouching down, or bunching in places you don’t want them to bunch – and that’s never a good time.

Luckily, though, armed with the inside information below you’ll be able to tame your wild boxers every time you wear jeans from here on out.

Let’s jump right in!

Boxers or Briefs with Your Favorite Jeans?

The first real piece of the puzzle you’ll want to get right is figuring out when to wear boxers and when to wear briefs (or boxer briefs) with the jeans that you choose to wear that day.

As we highlighted above, boxers are generally pretty loose, pretty comfortable, and pretty casual – and they go really well with looser jeans, shorts, and chinos.

You are going to get the world of support out of boxer shorts so you want to be sure that your days going to be pretty laid-back and you’re not going to be knocking things around when you run all over the place.

Boxer briefs are best with slimmer fitting jeans and active clothing when you expect your underwear to provide a little more support and a little more stability.

If you need to keep “the boys” nice and protected when wearing a pair of stretch fit jeans that you’ll be moving around in it’s not a bad idea to choose boxer briefs that day.

Pairing Boxers With Jeans

As far as general guidelines are concerned, it’s never a bad idea to match your drawers to your denim.

Below we highlight some of the more common types of jeans you’re probably going to find yourself wearing every now and again.

We also go over the types of boxers or boxer briefs you’ll want to wear when you have those jeans on, guaranteeing a fit that’s going to be a lot more comfortable and a lot more supportive than it could have been otherwise.

Here you go!

Traditional Fit Jeans

Traditional fit jeans are going to be a little bit boxy by nature. That means you’re going to have a lot more room in the front and the seat of these jeans to fit any kinds of boxers you want to wear.

You can go with boxer briefs if you’d like a little more support or you can go with full-blown silk boxer shorts, it really doesn’t matter.

The jeans aren’t going to force your boxers to move or ride the way they might have with a different kind of fit, and generally you’ll get just the right amount of support from your jeans and won’t need it from your boxers alone.

Go with what works best for you!

Relaxed and Straight Leg Jeans

Relaxed and straight leg jeans are (usually) a little bit tighter fitting than traditional fit jeans, and that means that your “wiggle room” is going to be a little bit limited.

Most people trend towards boxer briefs or tighter fitting boxer shorts when they find themselves wearing these kinds of jeans. That’s not always going to be the case (some relaxed fit or straight leg jeans have more room around the middle), but it’s a good rule of thumb to stick with.

Thankfully, these jeans aren’t so tight up against your body that you’re going to have to worry about “boxer boundaries”. You can wear whatever you like (for the most part).

Skinny Jeans

Skinny jeans are entirely different animal, though.

These jeans are going to fit right up against you like a second skin, many of them looking like they were painted on, with plenty of stretch and movement to make them (somewhat) comfortable – but they aren’t friendly to every kind of boxer out there.

You’re going to want something light, something thin, and something pretty discrete but you’re also going to want something that is super comfortable and supportive.

Expect a hunt for a while when you’re on the lookout for underwear to slide on when you are wearing skinny jeans.

Most of the time you’ll want to lean towards boxer briefs with a low profile, helping you to avoid your boxers “printing” on your jeans and looking a little silly in the process.

Fit is everything when you’re looking for boxers to wear with these super tight jeans.

You want something that conforms to the fit of your skinny jeans rather than something that fight back against them, causing all kinds of bunching and bulging that you’re probably not after.

Low Riders

Low ride jeans come into and out of style all the time, and if you’re feeling like showing up the sixpack that you been working hard on (or have recently landed a modeling gig at Abercrombie) you want to make sure you have the drawers in your drawers to wear with these pants!

Choose the wrong kind of boxer with these jeans and you’re going to be dealing with all kinds of bunching. Not only is that going to generate a world of discomfort but it’s also going to cause a really unattractive look – and slippage is always a problem, too.

The ideal here is to go with fitted boxers that have a longer leg, like boxer briefs with a low thigh to them.

Combine that with boxers that are low ride themselves to match the profile of your jeans and you shouldn’t have to terribly much trouble with these kinds of jeans (aside from wearing low ride jeans in the first place, anyway).

As always, shop around to find yourself a good pair of boxers that you feel comfortable in above all else.

It’s not a bad idea to have a couple of different types of boxers around with a couple of different fits to cover all of your bases when you pull different jeans out of your wardrobe.

How to Wear Boxers With Jeans

Boxers or Briefs with Your Favorite Jeans?