Summer has arrived, bringing scorching temperatures across much of the country. In this heat, shorts are a sensible choice for men. However, some men still manage to tarnish the reputation of shorts, making them seem “too casual for gentlemen.” These are often the same individuals who ruined sandals by pairing them with bright white ankle socks.
gentleman’s guide to wearing shorts
Seriously, Jerry. Jean shorts, socks and sandals, and, my goodness man – are those BluBlockers? We’re no longer friends.
Don’t worry; you can avoid looking like Jerry by following a few key principles. Recently, there have been many articles discussing the appropriateness of shorts for men. Some offer good advice, while others suggest terrible faux pas as acceptable. I particularly disagree with the ideas of high costs and cutoffs. Here’s The Sharp Gentleman’s guide to wearing shorts with style.
*If your name is Jerry, no offense intended. It’s just a random name.
When Can You Wear Shorts?
This is a fundamental question that deserves attention. Lately, there’s been a trend of pairing shorts with a full suit, which is not suitable for a modern gentleman. While celebrities or performers at events like MTV galas can pull off such outfits, it’s not a look for everyone. You are not Pharrell Williams, so it’s best to avoid this fashion choice. A quick Google search will show you many men attempting this look—and failing miserably. Trust me, this advice is for your benefit.
- When the location, event, or temperature is appropriate and
- When you are intentionally dressing casually (not conducting business or attending a formal event)
The key point here is that shorts are appropriate only when the situation calls for it. Note the “and” instead of “or” between the two points above. Let’s walk through a few scenarios to illustrate:
- You’re at an outdoor summer (yes) wedding (NO).
- You’re on vacation in Key West (yes) and invited to a beach dinner to discuss business with another executive (no).
- You’re golfing in July (yes, but be mindful of the Do’s and Don’ts).
The appropriateness of wearing shorts hinges on the context and the casual nature of the situation.
The Do’s and Don’ts of Wearing Shorts
DON’T: Wear Jean Shorts (Jorts)
Jean shorts are never appropriate. Despite some recent articles suggesting they’re back in style, they’re not. Wearing jean shorts is a surefire way to look like a dad on vacation at Disneyland or, worse, a Joe Dirt lookalike. Avoid cutting your jeans into shorts too—this is never a good idea.
DO: Wear Flat-Front, Tailored Shorts
Flat-front shorts offer a modern, sleek look that pleated shorts just can’t match. Pleats have been out of style for years and, while they’re starting to make a minor comeback, they were overdone in the 90s. Today’s gentleman should opt for flat-front shorts that fit like dress trousers, ending at or near the knee. Baggy shorts will make you look younger in an unflattering way and can give you that dreaded chicken leg appearance.
DON’T: Wear Shorts with Strings or Giant Pockets
Cargo shorts are debatable, but the older you get, the smaller your cargo pockets should be. By your 40s, avoid them altogether. Stay away from shorts with tassels, strings, or unnecessary pockets and loops—carpenter shorts are a no-go unless you’re actually a carpenter. Also, avoid convertible pants that zip into shorts unless you’re on a camping trip.
DO: Show a Little More Leg
Showing a bit more leg can be stylish. Shorts with a 9.5″ tailored fit or an 8″ Euro fit will sit just above the knee for most men, providing a modern look. While a 5″ inseam might be too short for some, avoid the overly long shorts we wore in the 90s.
DO: Embrace More Color Than Simple Khaki
Step out of the monochromatic khaki comfort zone and embrace colorful and patterned shorts. These aren’t just for golfers anymore. A more vibrant wardrobe is a sign of a modern gentleman.
DON’T: Wear Gym Shorts or Board Shorts in Inappropriate Settings
Athletic shorts belong in the gym, and board shorts are for the beach. Californians might wear board shorts everywhere, but that’s an exception. Choose classic chino shorts for most settings. Athletic shorts should sit just above the knee, and running shorts are shorter for practicality. Swim trunks and board shorts should also be above the knee and worn only near water.
Further Considerations
Now that your shorts game is on point, let’s talk footwear. The right shoes can make or break your outfit, but fortunately, this part is straightforward. You’ll need three types of shoes to pair with your shorts:
- Boat Shoes – Sperry Topsiders are an excellent choice.
- Canvas Shoes – Opt for styles that are lighter in color than your boat shoes.
- Athletic Shoes – Use whatever you wear for working out, running, or casual activities.
Start with a pair of brown or tan boat shoes and lighter-colored canvas shoes. Mix and match these with your shorts and shirts to create stylish summer outfits. Don’t forget to add some color to your shirts and shorts to make your look pop.
Lastly, be cautious of brand recommendations in other fashion articles. There’s no need to spend $300 on a pair of shorts just because it’s trendy. You can look fantastic without breaking the bank. Stay smart about your choices, and you’ll find that good fashion and savings can go hand in hand. There are plenty of resources to help you improve your style, so don’t hesitate to seek advice if needed.
