10 Best Classic Boxer Shorts for Men (Not the Tight Ones)

If you’re wearing boxers as sleepwear or if you want to incorporate some pattern into your routine in a fun, interesting way – these aren’t plain ole “tighty whities,” after all–a mix of eye-catching pattern options from J.Crew is a safe bet.

As with most menswear essentials, I find that J.Crew delivers quality and accessibility, right down to these boxer shorts.

They’ve got as many pattern picks as you might expect from a brand that designs such a wide array of men’s clothing, each more fun than the last. And they haven’t skimped on quality, either: Each pair is made from soft cotton with that classic, comfortable elastic waistband.

For as easygoing as it can be to wear boxers with a more relaxed cut, some still prefer a slimmer style of boxers, and that’s where Nice Laundry has options for your wardrobe.

As for me, I already appreciate and practically swear by Nice Laundry loungewear, which is super-soft to the touch and incredibly comfortable – that holds true for its lounge shorts and lounge pants in particular.

I also appreciate that they offer a timeless set of slim-fit boxers in Black, the kind of minimal pair you can wear if straightforward style is more your thing than a loud and flashy set of boxers.

Stretch pima cotton provides a soft feel against your skin, while the ribbed elastic waistband ensures a sleek fit, too.

There are only a few brand names that are synonymous with one key item of clothing for men – take Calvin Klein and boxer briefs, for starters.

The OG brand still makes some of the best men’s boxer shorts, and that includes every stitch of soft cotton construction and a durable, stretchy waistband.

Consider these a timeless choice that are also complemented by modern elastic leg openings.

At WERD, we appreciate when a brand sticks to its guns time and time again, like British outfitter Sunspel. They’ve been doing things carefully, stylishly and with exceptional quality in mind for decades, be it designing a James Bond-approved polo or perfecting the T-shirt.

Its Boxer Shorts are no exception – there’s no fuss, no frills, just the best materials on the planet and an eye for timeless design.

Using cotton poplin and double-turned seams–both for durability and to prevent fraying–sets these boxer shorts apart from the pack. They might be pricier than others, but they’re certainly worth it.

This NYC-based brand built its company on making the best underwear, from briefs to boxers, with a focus on soft, breathable fabrics and a range of cool colors and patterns.

In fact, my first introduction to the brand was buying a pair of both its famed boxer briefs and its traditional boxers, and the difference was immediate – they quickly became a favorite and soon took over my top drawer.

You get the best of the best with the 24/7 Woven Boxers, designed for all-day wearability thanks to the brand’s COOLMAX technology and anti-odor functionality.

The term “classic” might be right in the name of these Polo Ralph Lauren boxers, but that’s not the top reason we think they’re a truly iconic option when it comes time to shop for the best boxer shorts.

In fact, it makes sense to me that Ralph Lauren makes a high-quality pair of boxers, because they’re a traditional menswear staple every guy needs – like a Ralph Lauren polo shirt or logo T-shirt, for instance.

And take it from me: It can feel good to get a touch of value in your basics rotation for an agreeable price.

It’s the use of lightweight cotton, combined with prints that are engaging and appealing–but not over the top–that really won me over. The fact that they’re a nice value for a three-pack isn’t half-bad, either. Consider picking up a Ralph Lauren tee as you shop, too.

Seeking some bang for your buck when upgrading your basics drawer? Look to a retailer you can trust, like Banana Republic.

The brand’s cotton boxers come in a handy three-pack, all the better to keep you covered through at least part of your work week in comfortable, breezy style. The price is such that you could outfit yourself for more than a week’s worth of wear by purchasing multiple three-packs, and considering the all-cotton construction and stay-put elastic waistband, why wouldn’t you want to do that?

Menswear doesn’t always follow the old adage that what’s underneath really counts, especially when tailoring and refined staples are on full display. But there’s something to be said for a luxurious upgrade as far as the best men’s boxer shorts are concerned, and Derek Rose delivers absurd quality.

From cotton to silk satin, there’s a range of fabrics and styles for every taste.

When upgrading your top drawer, reaching for the classics is sometimes in order. Fruit of the Loom gets down to business with a lightweight cotton-poly blend featuring a comfortable tag-free design, and the affordable price for a multi-pack is another added bonus.

These are also designed with a leg opening that doesn’t bunch or bind, and the fit should prove classic and comfortable.

The best boxer shorts tend to come down to fabric and fit – after all, the layer closest to your body should perform, move with you and simply feel great to wear.

In the case of these classic men’s boxer shorts from Hanes, the difference is in the details, like a stretchy cotton-poly blend and a durable, comfortable waistband. A range of stylish colorways amp things up nicely, too.