Building an outfit from the ground up mostly starts, literally, from the ground up–or rather, the top down, when you consider your basics drawer (it’s the first drawer in your dresser, right?). Consider boxer shorts. First crafted for the mainstream market by Everlast in the 1920s using an innovative elastic waistband, the boxer short offered better mobility and comfort than other undergarments at the time, and the best boxer shorts still do much the same today.
Boxer shorts are a garment defined by their inseam length–usually about mid-thigh on most guys–and their cut, which is much looser than form-fitting boxer briefs (which we’ll also cover at WERD sooner rather than later). The best boxer shorts can function as sleepwear as readily as they can work with pants that feature a more relaxed cut–airflow from top to bottom is crucial on hot days, or if you tend to run hot in the first place.
The best boxer shorts now even feature technical fabrics and moisture-wicking, temperature-regulating properties, something even Everlast didn’t see coming nearly a century ago. The key when shopping for boxer shorts? Looking for quality fabrics and designs, and being prepared to spend just a bit more for a top-notch pair–we’ve got picks for every price point below as you look to upgrade your basics drawer.
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. They’ve got as many pattern picks as you might expect from a brand that designs such a wide array of 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.
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?
If there’s one thing we love about a capsule collection–or a brand to begin with–it’s a sense of versatility and adaptability. The Everlane Uniform Collection, as we’ve talked about at WERD, takes everyday essentials and combines them in one offering that’s as easy to mix and match as anything out there (take the idea of pairing an Oxford shirt with chinos – or denim – and you get the idea). They’ve also got you sorted out in the basics department, using a blend of Supima cotton and elastane for laidback comfort and day-in, day-out wearability.
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. Specifically, they’ve got 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.
We here at WERD 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 normal, but they’re certainly worth it.
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. It’s the use of lightweight cotton, combined with prints that are engaging and appealing–but not over the top–that really won us 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.
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. 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.
Some guys just want only the best of the best in every category, and we’re certainly not going to blame you for seeking out upgrades aplenty from A to Z. If you want a pair of boxer shorts that rise above the rest in terms of pattern, print and fabric, the exceedingly soft and stylish woven boxer shorts shown here quite simply take the cake. Consider them a splurge for special occasions.
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