https://twitter.com/dieworkwear/status/1820623940110504242
The reason why guys are afraid of shorts is because 1) they’re shy and afraid of standing out, 2) they have pale legs, and 3) they don’t know how to style them. For the first, stop being a baby; for the second, go get at tan; and for the third, here are some styling ideas https://t.co/Pwdfk3HUTk
IMO, shorts are easier to wear then they’re obviously casual. That means avoiding things that look like slim chinos cut off mid-thigh (see pic 1). Instead, go for something more obviously casual, such as a pair of shorts that hover around your thigh like a hula hoop.
So let’s start with some simple styling ideas. These Imogene + Willie shorts have a nice cut and would look great with a t-shirt and some simple sneakers. The baggier cut is what makes this obvs casual and not like slim chinos cut off at the thigh (which is toddler-like)
Another easy styling idea: wear shorts with a long-sleeve knit. This can be a long-sleeve t-shirt, merino sweater, or even a hoodie if it gets cold enough. Again, notice these shorts are looser and cut a little shorter.
If you want to go a little sportier, you can also do something like Patagonia Baggies or a pair of sweat shorts. Again, wear with a long-sleeve knitted top, like a long-sleeve t-shirt, sweatshirt, or hoodie. Also sneakers (with or without socks, up to you).
For more of a workwear vibe, try a pair of shorts made from military sateen fabric or has camp pockets (including cargo pockets). Look up brands like Engineered Garments or Frizmworks. Wear them with parkas and hiking boots.
For more of a laid back 1970s California vibe, consider shorts made from needlecord (corduroy with fine ribs). These look great with t-shirts, Vans sneakers, and some retro-styled rugbys. Birdwell Britches and Save Khaki United have cord shorts (although SKU runs a bit slim)
You can also go bohemian with shorts from brands like Harago or Kartik Research. Wear with one of their embroidered tops, a simple t-shirt, or a guayabera. Also with huaraches while listening to Yusef Lateef or Alice Coltrane records.
Or you can channel the energy of Gary Cooper visiting Acapulco in 1953. Wear a pair of patterned shorts with some simple espadrilles and a guayabera.
It often helps to have some kind of layering piece, even if that’s just a chambray shirt layered over a t-shirt. Or a long-sleeve knit. Anything to make the outfit a little more interesting (along with using distinctive cuts).
Camp collar shirts are also an easy way to make a short outfit look a bit more interesting.
I can already heard the exhaustingly cliche line. “A don doesn’t wear shorts,” says a man standing in line at this Taco Bell inside a Target. First of all, you are not a don. Second of all, that episode was literally about a don (Tony) wearing shorts!
There are situations where shorts an inappropriate, but such situations are limited (weddings, funerals, and very conservative offices). But most people don’t spend all their time in those spaces. You have to figure out if shorts work for you.
The idea that men shouldn’t wear shorts seems weirdly Victorian. Even the king of Spain wears shorts! George Plimpton wore shorts! Just lean into the fact that they’re casual instead of doing the slim-fit, tidy aesthetic.
