Summer’s Hottest Trend: 5 Stylish Ways to Rock Boxer Shorts

Of course, as far as really pushing fashion to the edge goes, very few trends have been as intriguing or as bold as the “underwear as outerwear” movement. We’ve gone from iterations of Emma Corrin boldly wearing her Miu Miu pants at the Venice Film Festival to Bella Hadid pairing tighty-whities with UGG boots. While these fashion-forward choices have certainly been making a statement, not everyone feels comfortable strutting out in what amounts to essentially lingerie. Luckily, there’s a more laid-back—yet just as stylish—alternative that has taken the summer by storm: boxers.

Boxer shorts are the perfect blend of comfort and cool, offering something menswear-inspired but both on-trend and very versatile. These shorts bring together the best of your go-to sleepwear and fashionable streetwear, thus becoming the summer wardrobe essential. Boxer shorts are about to be this summer’s ultimate staple, whether you’re looking for classic boxer briefs, oversized fits, or luxe fabrics such as linen, cotton, or silk. They will give the relaxed vibe without having a blow to the style—something necessary for those sweltering days when dressing for the heat is the priority.


It’s this versatility that really lends charm to boxer shorts. They can be dressed up or down, depending on the occasion; although they do come with a couple of styling challenges. One example is that they could ride up when you sit down, which can get quite uncomfortable or sometimes even embarrassing. Also, as they were created initially as underwear, boxers might not be very fitting for all body types, and sometimes, they can appear way too casual for a specific situation. So, amidst all these potential setbacks, I decided to take matters into my own hands and see if I could style some boxers to work for all occasions so that I could see if it’s doable to wear them every day and stay stylish.

First, the classic combination: boxer shorts with a baby T-shirt. This pair screams summer like ice cream cones on a really hot day. Simplicity, in the form of a baby T-shirt, mostly with a graphic design, is casually matched with the easy, relaxed fitting of boxer shorts. I added tall boots and a metallic handbag to give some attitude. This overall is a great outfit to wear to everyday events, like music festivals or just hanging out with friends; you only really need to choose appropriate boots for the terrain involved, but other than that, this look is casual yet stylish.

For those working in a relaxed office setting, I did manage to get away with boxer shorts at work. Of course, this all depends on your office dress code, but these oversized, dark-colored shorts from Free People have a little something business casual about them. I added a crisp cotton shirt and leopard-print ballet flats to really dress it up. Add on a blazer or leather jacket for cooler days, and you not only get some added warmth but also layering to your outfit to really dress it up. Somehow, that proves that with the right accessories and layers, even boxer shorts can be viable in more formal settings.

One of the standout pieces I experimented with was a matching set from Pleasing. The set consisted of a pair of boxers and a matching vest in thick, heavy-feeling cotton fabric for the outside. The thing I enjoyed most about this outfit’s design is the fact that it’s simply so versatile. The matching vest really adds a little bit of sophistication that might otherwise have been lacking, especially while being worn with some structured blazer and bold accessories. This is a really nice ensemble for days when you would like to spend your time shopping or just having casual drinks with friends and not put so much effort into how you dress.

Wearing boxer shorts around for several days, I found them most useful for running errands, like juggling bags of groceries or simply grabbing a cup of coffee on the way. Boxer shorts offer that comfort and ease you need for a busy day. Here, for a basic, casual outfit, I matched the boxer shorts with some simple T-shirts, tank tops, and added a light button-down for extra coverage. Finally, add some sneakers to complete the look, and you instantly have something practical yet stylish. This works very well for those very busy days when you have so much to do but still want to look chic and relaxed in your outfit.

One of the most versatile looks I tried was a version of the waistcoat-and-boxers outfit that had seen on Pinterest. This quickly became one of my favorite combinations, which I’ll be wearing throughout the rest of summer and into early fall. This goes well with a few types of shoes, be it casual trainers or heeled sandals, even knee-high boots. That is the kind of look that will work for so many kinds of situations, from dinner to going out with the girls. It is the perfect blend of comfort and style that makes it one of those go-to outfits for this transitional season.

After playing around with different ways of styling boxer shorts, I grew to really love how versatile and comfortable they are. Initially being introduced to menswear, boxer shorts are undoubtedly finding their place in the fashion and functionality departments for women, too. Styled right, these shorts can be worn for nearly every occasion. So, if you are looking for some new trend to embrace this summer, then boxers are definitely the way. You will be surprised that they can fit in with refreshing fashion into your wardrobe for summer.

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