Every Year, I Buy One New Pair of Baggy Shorts. Here’s What I Chose This Summer.

My baggy-shorts hunt begins on the Lower East Side with KOTN. Now, I openly admit this isn’t a brand I run to when in need of fashions: I’ve only ever purchased one thing from here, a striped short-sleeve ringer tee that I picked up and wore right away after spilling an iced coffee on myself. But I decided to give KOTN a go once I found out that it has a big breezy pair of linen shorts I could try on. Full disclosure that the Cairo linen shorts are the smallest pair of the bunch and also my least favorite, but that’s only by comparison. They are lightweight, breathable, and come in three colors: natural, dark taupe, and maritime (a dark blue). At $98, they are decently constructed and the bargain purchase of this group, so I’d still recommend them.

My wild-card entry comes from Ron David Studio. Not initially on my list, the Orchard Street shop caught my eye as I was walking from KOTN to Colbo, and I’m glad I took a peek inside. Upon entry, I was met by an array of colorful and vibrant pieces ranging from textured blouses, to cycling jerseys, to a wonderful pair of very large gymlike shorts that are the subject of this portion of my entry. The studio’s Oversized Wide Unisex shorts are 100 percent cotton and come in black and navy. They have a slight sheen similar to that of basketball shorts that give them a very athletic aesthetic. Like a lot of athletic shorts, they are “one size fits all” with a comically stretchy elastic waist that I estimate would suit anyone from a 26- to 40-inch waist. They areÜber-wide and make it more than halfway down my calf on my six-foot-one frame, easily making them the largest shorts I tried on during my shopping trip.

[Editor’s note: Ron David Studio’s website is under construction, so you can’t buy these online. But they are available in store, and we’ll update this link when the new site is up.]

The award for the most sophisticated shorts on this list goes to Colbo’s Linen Dress Shorts. They are the upscale version of the KOTN Cairo linen shorts, and at $410 they are worth every penny for someone looking to add a wide-fitting, well-tailored pair of shorts to their wardrobe. This pair is so well structured, luxurious, and soft to the touch that I would go so far as to say they’re even appropriate for a fancier occasion with a looser dress code despite their billowiness. Even with their lavish quality, I think their versatility is by far their best characteristic.

Every year a portion of my search is relegated to online shopping, and this summer I have narrowed it down to two brands that unfortunately don’t have New York City brick and mortars … yet. The first is Brigade. This Brooklyn-based streetwear brand run by couple Sarah and Aaron Maldonado has been making stylish and sporty clothing focusing on superb craftsmanship for just over a decade now. These shorts are no different. Made with 100 percent cotton, the raw denim bottoms are priced at $168 and come with some interesting embellishments, namely the pearl rivet-lined pockets, gemstone designs patterned down the front of each leg, and “Brigade” written in cursive and stitched across the rear under the back pockets. The fit is a very sturdy and wide one with the length just covering the entire knee. I would pair these with a simple white tank top or T-shirt, as the shorts will likely be the statement piece of any outfit they’re a part of.

For my second online option, we need to head across the pond to London to shop with SCRT Co., short for Screen Test. This is a brand I discovered while in Paris a couple of summers ago after stumbling upon its showroom during Paris Fashion Week, and I’ve been keeping up with it ever since. I was excited to see a big baggy shorts option hit the site this month, and as the name suggests, the gridstop pleated shorts have contrast grid stitched throughout the garment that give them a very technical look. The fit, of course, is big and baggy and finishes below the knee. While pretty lightweight, the ripstop fabric is woven with such tightness that they could block out cooler air, making them suitable for transitioning into the fall months. I could certainly see them paired with a heavier top or a water-repellant Arc’Teryx jacket to complete a stylish gorpcore fit.

Awake NY became one of the preeminent streetwear brands during the 2010s, amassing a large and loyal following based on a cool factor not seen since Supreme. The Classic Striped Shorts in green, also available in white, were my favorite shorts of the day. The cotton weave along with the stripes give this piece an interesting visual texture akin to something you might find at a brand like BODE, but the Awake shorts possess a little more street cred. After trying them on I was genuinely shocked by how soft and breathable they were. I mean, these shorts are great. They are perfect for the beach, for lounging around your apartment, for a quick errand; they would even be great for a night out with the right shirt and shoes. I could definitely see them paired with a crisp white Polo Ralph Lauren oxford, ribbed dress socks, and a pair of black loafers, juxtaposing their relaxed fit to complete a trendy downtown look.