Top 10 Shorts Wearing Do’s & Don’ts! | How to PROPERLY Dress Up Shorts

May 2, 2022
Shorts are a men’s summer essential that cause the most problems when trying to look sexy. The truth is a razor thin line exists between looking amazing and looking like a huge dork. With that, I’m going to go over shorts wearing rules plus a few ways you can rock shorts better. After that, I am going to show you some of my favorite ways to dress them up.  Check out this other summer essentials video!

Rock your shorts better

  1. Nail the fit – The legs should not be too big or baggy, the leg should not be skintight, and you should be able to pinch about an inch on each side.
  2. Don’t wear pleats – pleated shorts are a deal-breaker. Find shorts that have a clean flat front for a better aesthetic.
  3. The length matters – do not wear shorts that touch your knee or cover your knee. Have at least one or two inches above your knee. Keep in mind that 5″ shorts look different on a shorter man than a taller man and are a more casual look (also for working out). 7″ shorts are better for dressing up. 
  4. Be choosy with your colors – if you’re going to be dressing up your shorts, stick to the solid pallets. Tans, navy blue, grays, and blacks are great choices.
  5. Experiment with more bold and playful shorts — step outside of your style box with vibrant colors and patterns. Make sure to pair these bolder shorts with a more muted shirt.  I pair my camo shorts with a black top and sneakers. 
  6. Say ‘no’ to cargo shorts — they are a bit longer, and the pockets are bulky.
  7. Say ‘yes’ to jean shorts or jorts — both are stylish, and jorts look great cuffed.
  8. Upcycle your old jeans — create shorts from your retired denim. 
  9. Cuff longer shorts — the cuff is an appropriate style and an easy way to shorten the length of your shorts.
  10. Learn to dress your shorts up and down — switch from casual to next level by simply changing shoes, belt, and/or shirt.

My favorite ways to dress up shorts

  • Simple, clean summertime perfection – minimal leather sneakers + a pair of flat front tan shorts + a polo untucked. To take this outfit next level, tuck the polo in, switch out the sneakers for some loafers, and add a belt. This outfit is great for an evening out.
  • Dressing up shorts for date night – with the same shorts and loafers first from the previous outfit, wear a simple t-shirt with a cardigan. If the temperature gets too warm, take off the cardigan.
  • Fun and sporty summertime look – 5-in shorts with fashion sneakers and a black hoodie makes a sexy and fresh outfit.
  • I’m in love with this outfit – navy suede slip-on sneakers + a navy-blue sweater + light gray shorts is playful, fun, and fresh.
  • James Bond on vacation – simple black loafers and a matching belt with shorts and a polo.

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