Hello, my name is Lily and I am a men’s shorts expert. Ever since I was just a young don, I’ve been thinking about shorts 24/7. One of my earliest fashion meltdowns was in a Boston Filene’s Basement (RIP) over a matching Phoenix Suns jersey and shorts set I needed my mom to get me. (As a confused 10-year-old, I was obsessed with Charles Barkley and wanted to live with him in a McMansion in Phoenix.) This was the beginning of a lifelong search to find my masculine identity, all while being blessed with childbearing hips and the massive sweater puppies that my Sicilian grandmother passed down to me.
I’ve always thought that each pair of shorts had the potential to change my entire personality — no, my entire life. To me, shorts are easier to shop for as a transmasc-presenting person because, compared to regular pants, there is a bigger diversity of style to play with. Certain types of shorts can take on an almost costumelike quality, letting me experiment with some of my favorite masc identities. Shorts make me feel like a man, but not just any man — every type of man I want to be. Depending on the fit, shorts can transform someone into a soccer player from Real Madrid, an ’80s surf instructor, a seasoned hunter, all the fab skater boys from Clueless, or even a kindly gay uncle. Over a year ago, I had top surgery to give me the beach-dad bod I’ve always wanted, and this has only fueled my desire for more shorts.
For some of us bad boys, classic beach-body insecurities mixed with run-of-the-mill gender dysphoria can interfere with summer fits — but don’t fear the short. There are options for all types of bodies on this list, whether you want to look taller, hide the hips, or generally look like the coolest person on planet Earth.
There are many shorts-related identities I crave, but one of my most treasured has always been a teenage boy who wears Dickies and can do a sick ollie. The only problem is that whenever I try on the classic work shorts, I look like a tree stump because they are so wide and long. Meet the Slim Skateboarding Shorts — still the same baggy look but just a little slimmer in the leg and with a shorter, 11-inch inseam. Dickies fabric is sturdy, which lends itself to a straight, boxy, masculine silhouette that hides curves. I’m five-foot-five, if you were wondering, and I usually size up in the waist with Dickies because of the aforementioned hips that don’t lie.
To me, the crinkly nylon shorts from Champion are what an extra in GoodFellas would wear to power-wash his driveway. The leg width is, ahem, wide, making you look slender. They fit a bit above the knee to give you a longer silhouette. And they won’t break the bank. The bright red is my fave, but they come in several colorways, so collect them all. These can be worn to the beach or to an alfresco trattoria paired with a funky Hawaiian shirt. Okay, now I’m craving Italian ice.
Make the deli guy think you walked right off the goddamned runway. These are sweat shorts you can wear to the club or to a cozy Ultimatum: Queer Love viewing party. Eckhaus always got those funky earth-tone patterns. Waterworld, but make it Milan. These investment shorts that range from $150 to $250 will fit a variety of body types. An international DJ I know wears them every day.
Did you ever think it was possible to look crazy/sexy/cool while kayaking? I’m here to tell you that it’s possible with these water-repellent hiking shorts that look good on everybody. Shorts this durable will allow you to paddle right up to a vegan BBQ–poetry reading. Bonus points for the chic gorpcore belt.
Fucking Awesome is a skatewear brand out of L.A. that makes high-quality clothing with ferociously cool patterns. These shorts are going to set you apart from the rest of the queers rocking Realtree camo this summer. The print is a little diff — it’s still giving hunter, but this hunter is also an award-winning photographer. Relaxed fit.
Be the sexy surfer of your dreams in these classic ’90s-influenced trunks. Personally, I have zero balance, so I’m relegated to rocking them while boogie boarding, but don’t worry I still look cool … I think. There’s a reason why Stüssy is a classic — it continuously puts out sick shorts every season, plus they’re mid-price, clocking in at 70 bucks, and will last you many a summer.
I bought my first Polar pieces as a treat to myself after doing five years of back taxes, so that should tell you something about how inspiring these shorts are. All of Polar’s clothes fit oversize and boxy for a straight manly silhouette. These are Y2K-style boardshorts with some goth contrast stitching. You will be respected and feared in these!
These are for my short kings who want to look taller or for anyone who wants to show off their gams at the pool. These will make you look like a hot gay guy from the ’70s. Fit, mate!
eBay is where I primarily live my life — we all want jorts, and every pair of jorts is better used, worn, and broken in by a random man from Ohio. eBay is always a bit of a gamble size-wise, so buy a tape measure and get all tinker-tailor-soldier-spy on your ass. Here are some things you will want to search for: “LEVI’S 505 SHORTS,” “WRANGLER SHORTS,” “OCEAN PACIFIC, SURF VTG NWT,” “90S TOMMY/POLO,” “AGASSI,” “JNCO” — if you nasty.
The Strategist is designed to surface the most useful, expert recommendations for things to buy across the vast e-commerce landscape. Some of our latest conquests include the best acne treatments, rolling luggage, pillows for side sleepers, natural anxiety remedies, and bath towels. We update links when possible, but note that deals can expire and all prices are subject to change.
