7 Shorts a Man Should NEVER Wear

May 1, 2023
Today we are talking about a men’s summer style essential, shorts. Shorts are one of those items that cause a lot of men stress and anxiety because they either hate their legs or don’t know how to rock shorts properly (looking like a dorky dad). A man’s style sensibility is destroyed if the shorts are not appropriately paired or not the correct length or pattern.

I want to get a couple of things out of the way first. (a) Yes, I shave my legs. (b) I have small calves because I ruptured my Achilles tendon years ago, and no matter how many calf raises I do, my calves will not grow. (c) Also, check out the most amazing shorts on the market: Cuts Clothing. They also have sexy Henleys, polos, tees, hoodies, and joggers.

Avoid dressing in these types of men’s shorts

  1. Big and baggy. This includes the leg and also the crotch. A super long rise will make your legs look extra short. Baggy shorts will also make small legs look like toothpicks. Upgrade the quality and style of shorts; they will fit better and look better. You can dress them up as well.
  2. Pleated. Pleats will make you look heavier in the midsection. Choose instead a clean flat front that you can dress up or down.
  3. Too long. The length can go anywhere from 5 to 11 inches and everything in between. One rule of thumb is if your shorts are passed the top of your kneecap, they’re too long. They must be at least three fingers above the top of your knee for the most aesthetic short length. If you’re 6 ft tall, 11-in shorts may land 3 inches above your knee which would be the appropriate break in your leg length. When shorts are super high, legs will look a lot longer. Wearing high shorts is a good thing if you’re a short guy. Check out my demonstration. Now, if you’re really tall and you have really thin legs, 5-in shorts will look a bit funny. Hike those shorts up a bit if you want to show off your quads. But it’s all personal preference.
  4. Without underwear. Nobody wants to see your Big Al, so don’t wear mesh shorts without underwear. Also, if you’re not wearing underwear, everybody can tell if you are circumcised or hung.
  5. Dressed up casual. Some shorts can be dressed up if they are the appropriate shorts. Check out my demonstration. Shorts with a drawstring and elastic waistband are not okay to be dressed up with a polo and loafers. But shorts with a flat front, zipper, button, and belt loops can be dressed up by tucking in and throwing on a belt. You could choose between minimal leather sneakers, flip-flops, or simple loafers.
  6. With socks. Sure, you can wear a pair of Jordans with casual athletic shorts. You can also wear a taller pair of socks when working out. But wear no-show ankle socks if you’re wearing minimal white sneakers or trying to elevate your shorts’ aesthetic. Also, there is no such thing as shorts in business casual. Nobody needs to see your calves and socks when you are rocking shorts.
  7. Not coordinated both ways. (a) When wearing bold shorts, do not pair them with a bold top. In other words, if you choose bright-colored or patterned shorts, go subtle or subdued with your top. (b) Ensure your outfit is coordinated top and bottom (color, pattern) while matching the level of casual vs. dressiness when pairing with shoes (flip-flops vs minimal leather sneakers vs loafers).

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