How Men Should Wear Shorts

Wearing shorts is one of the best ways to beat the summer heat and look stylish while doing so. Whether you’re lounging around the house, walking on the boardwalk or heading to the beach, you can look great in a pair of shorts.

How Shorts Should Fit

Shorts should lean towards a slim fit.

The key here is to buy a slim fitting pair of shorts that don’t bloom out at the bottom. You want your short to be consistently slim. You should have a bit of space to breath but not a lot of excess material flapping around.


If you’re more on the modest side, opt for a pair of shorts that end right at the knees. Otherwise, you can go up a few inches (not too much) right above the knee caps. Both styles work depending on what you prefer. Just make sure you don’t go too far down or too far up.

Key: Be objective, if you got chicken legs don’t go for a super short pair of shorts. 

What Styles To Wear

There are a ton of different styles to choose from. My top 4 picks for the best summer shorts are:

  • Chino Shorts
  • Denim Shorts
  • Athletic Shorts
  • Patterned Shorts

How NOT To Wear Shorts

Now that we’ve covered the way a pair of shorts should fit, the length, and the different styles to choose from, it’s time to go over some of the do not do’s of wearing shorts. 

Keep this handy image in mind when choosing your next pair of shorts.

Summer Shorts Go Great With

Now that you know the rules of picking our a great pair of shorts, it’s time to go over other clothing pieces that compliment a pair of shorts really well. Really the most important thing you need to pick out to go wish your shorts is your choice of footwear. The best shoes that go with summer shorts are:

  • White Leather Sneakers (Low Top)
  • Boat Shoes
  • Slip On Shoes
  • Canvas Shoes

Make sure with all your footwear you’re wearing a pair of no show socks. Trust me you don’t want to go sock-less.

Shorts Recommendations

Here are a number of shorts I highly recommend you check out that meet all the specifications of a great looking pair of shorts. (You can find a bunch of discounts for all these brands at our coupons page)

$: ASOS Skinny Chino Shorts

$: Dickies Slim Fit Shorts

$: Levi’s Slim Fit Denim Shorts

$: Nike Tech Fleece Shorts

$: Polo Ralph Lauren Shorts

Outfit Examples

Let’s end it off with some amazing outfits that really incorporate shorts properly. Hopefully this will give you some ideas on how to wear shorts.