How to Look Good in Shorts – The Ultimate Summer Guide – Gemsman

How to Look Good in Shorts – The Ultimate Summer Guide

How to Look Good in Shorts

We’ve covered a lot of ground on the fashion section here at Gemsman. Everything from summer street outfits, varsity jackets, to athleisure wear. One thing we haven’t touched on, however, are shorts. Wearing shorts can either make you look like a casual dude who knows how to laugh and have a good time, or a slob who didn’t expect to be seen that day. And there isn’t much middle ground. Here’s the comprehensive guide on how to look good in shorts – just in time for summer.

The Right Shorts

Long shorts (below the knee) and cargo shorts are beginning to trend again in luxury fashion, but I’d wait a couple years before boarding that bandwagon. For Summer 2019, stick to casual shorts that hit just above the knee and athletic shorts that hit an inch higher than that.

Get yourself a couple of good pairs of denim shorts and a couple of good pairs of casual canvas shorts. Levi’s makes great denim, and they’ve got great denim shorts. These 502‘s are already rolled a bit, so you can adjust for the perfect fit. The 511 slim shorts are also a good choice for a basic wash, and they also come in black. Neither of them are cutoffs, so I’d recommend either cuffing the shorts over once or even taking off the bottom half inch of fabric to get that frayed summer-days look.


For your non-denim needs, you don’t need anything fancy. Length and fit are far more important than the brand in this case. Amazon’s basic 7” short will hit at the right spot on your leg. You can go for the 9” if you need a bit more fabric to feel comfortable. The khaki short is a versatile color that will go with almost any t-shirt you throw at it (please don’t do red though). Beyond that, you should invest in a black or navy for a darker color, and also one lighter-colored fun pair. Amazon’s bright blue will go great with a gray t-shirt and white shoes.

How to Look Good in Shorts

To really work all the angles this summer, you’ll need good casual shorts and some versatile running shorts. Don’t be afraid to pull up at a backyard barbeque with the right pair of athletic shorts to do athleisure right! For running shorts, try New Balance’s Accelerate. The 5” variety will be great for running, but the 7” might serve you better for brunch. 

If you’re hitting the beach or pool, please ditch the boardshorts. In fact, remove boardshorts from your vocabulary unless you’re using it ironically to refer to your new “swim trunks.” Check out Speedo’s Swim Trunks which offer a classic surf style in navy color. They hit at the perfect length. Pair with

Shorts Styling

Shorts should hit about an inch or two above the knee for casual wear, and an inch higher than that for athletic wear.

Your shorts should stay up without a belt, even if you wear them with a belt. Look for a waistline that fits comfortably without sagging, and stays high and tight without pinching.

Don’t obsess over chino shorts (or pants for that matter). Chino is just cotton twill fabric, it isn’t a cut or a style.

Cutoffs and cuffing are great ways to give your shorts an edge. If you have an old pair of jeans or khakis, turn those boring pants into a pair of broken-in cutoffs. Cutoff denim shorts and a white t-shirt is a classic look that can be worn once a week. If you have shorts that are a bit too long, try cuffing them in the same way you’d cuff a pair of pants. If the shorts are too baggy if might not work, but then again, if the shorts are too baggy they should be thrown away in the first place. Get shorts that fit.

Shorts with Closed Toe Shoes

Matching closed-toe shoes with shorts is a game of chicken with bad fashion. Low cut shoes are the safe bet, but high tops can give you some versatility if you’re creative.

If you’re going for high tops, you can’t beat Converse. The white high-tops will look great with every single color of casual wear short that you can find. Pair them with black cutoff denim and a horizontal-striped colorful shirt. The black-high tops can accent an outfit with a white t-shirt or light colored hat.

How to Look Good in Shorts

If you look up men’s shorts on Google, Pinterest, or nearly any clothing retailer’s website, you’ll notice that over half of the shorts are paired with white shoes. And that’s a conservative number. A couple of good pairs of white shoes will get you through an entire summer with fresh looks. I’d recommend one good pair of black sneakers and one pair of fitted sneakers.

Nike’s Air Max 90’s in the white/black/jade color scheme is a daring block sneaker that will pop the color on your outfit without additional help. The Puma smash v2 are a great fitted pair of white sneakers for any outfit.

If you insist on sporting non-white shoes with your shorts, grab a pair of black Vans slip ons. Pair with high white socks (push them down a bit), lighter colored shorts, and a black t-shirt. Brown boat shoes are a standby for the preppy college look, great with shorter shorts and a sweater. If you go for the darker shoes know that this changes the color gradient of your outfit. Most men’s summer outfits go from darker on top to lighter on the bottom. If you have dark hair, it accents the gradient; blond hair contrasts the gradient. When picking shoes, watch how the color affects the way the outfit moves as a whole.

Every pair of shoes will also need the right pair of socks. Invest in both some no-shows and some quality high socks. No-shows should be true to their name: they should stay on your feet but stay out of sight. Champion offers a nice set of no-shows in a clean white color.

High socks should go above your ankle without choking out your calves. White is a great color for high socks, as anything else puts you in clown and circus territory. Goofy high socks are great when they peak out of the space between your shoes and pants. But when you’ve got shorts, they’ve got too much exposure. Keep it simple, keep it classy. Get the white socks. Black is also a popular color, but I usually don’t see it done well.

If you need to mix it up, grab some tube socks that have stripes, like these white ones with retro horizontal block stripes.

Shorts with Open Toe Shoes

Open toed shoes are the easiest type of shoe to match with shorts. There are two kinds of primary open toed shoes that you should invest in to make the most of your shorts.

Every guy should have a basic pair of Rainbow’s. They make summer outfits easy, and the brown looks good with every color. Get the dark brown. The lighter colors get dirty, and black flip flops probably shouldn’t be worn in any context. Rainbows will give your outfits a west coast, beachy vibe. Try your Rainbows with athletic shorts for casual days and sweatshirts for cool summer nights.

How to Look Good in Shorts

Also look for a pair of quality Birk’s. The brown are a classic look, but the white Birkenstocks are having a moment right now. Birkenstocks are a hip sandal that will last you for years. Use Birkenstocks for a retro hipster vibe. When you pop on the Birkenstocks, complete the look with a long sleeve and a dad hat.

If you insist on getting away with socks and sandals, you’ll need an athletic slide and a good pair of athletic shorts. Nike’s black slides will play well with white high socks and most pairs of athletic shorts. You might be able to swing socks and Birks, but for the most part, leave the socks for the closed toe shoes.

Completing the Outfit

For the most part, we’ve talked about shorts and shoes because it’s harder to match shoes with shorts than matching a shirt with shorts. Once you’ve got some shoes and shorts combinations in your wardrobe, it’s fairly easy to build out the shirts, hats, and accessories from there.

The perfect t-shirt for your shorts has a hemline that hits right at the bottom of your fly. The shirt should cover part of the shorts without covering your legs. That’s the rule. But once you know the rules, they can be creatively broken to make fashion statements. Get a great belt and tuck your white t-shirt into light washed denim cutoffs. Grab an extra long t-shirt that drops just above the bottom of your athletic shorts to make an entrance on the soccer field.

T-shirts aren’t the only tops you should look to match with shorts. Tanks and long sleeves have the same color principles, but can emphasize the outfit differently. If you go with a tank top, open toed shoes are the safer choice. Long sleeves pair great with Birks or closed toed shoes.

Collared shirts can give you a preppy flair. A patterned short sleeve button-up, like this zebra one or this pizza one, goes great with denim shorts. If you’re picking a button-up for shorts, you want something baggier than the fitted button-ups great for pants. Shorts and button-ups need some flow, and they need accessories. Pair the baggier button-up with tight-fitting shorts, sunglasses, and a strapped hat.

For summer nights and early breakfast, grab a crew-neck sweatshirt or bomber jacket. Keep the crew-necks with the same hemline as a t-shirt, hitting just at the bottom of the fly. You may have to purchase a size bigger to get the ideal length. Bomber jackets pair nicely with a t-shirt and shorts. Make sure there’s about one to two inches of t-shirt peeking out below the bomber, and another couple inches of shorts below that. The right layering will make the shorts, shirt, and bomber flow perfectly.

Playing With Colors

As a general rule, don’t match colored shorts with colored shirts. Black shorts and a gray shirt is fine, but blue shorts and a red shirt makes you look like you’ve put on your team colors for a local sports game. You usually want to create contrast between the shorts and shirt (unless you’re going for a monochrome look). If you have darker shorts, pick a lighter shirt; if the shorts are lighter, go for a darker shirt.

Blue shorts look amazing with light gray shirts and white shoes, or black shoes and a white shirt. Blue is a peaceful, vibrant color that will bring up the volume on your basics without drowning them. Mix blue with white shirts that have a touch of yellow or green for a casual look.

Green shorts have a lot of room to play. They go well with brown boat shoes or Rainbows for an earthy base. Try green shorts with white shoes and a white top for a clean look (accent with a yellow dad hat).

White and black shorts can be paired with nearly any colored t-shirt. Don’t waste the black and white shorts on neutral shirts, use them to bring out the heavy hitters in your quirky t-shirt and quirky button-up collections. Pair with brown Birks or Rainbows.

Denim shorts vary a lot depending on the wash. For a black wash, wear them like any black shorts–although definitely head for high top white converse with the black denim shorts. A light wash denim short creates a great monochrome outfit with gray t-shirts and white shoes. Regular blue wash denim shorts work well with neutral colors, hoodies, and white shoes.

How to Look Good in Shorts: Conclusion

If you got lost in the shuffle, here’s what you need to know:

  • 7” and 9” shorts are great for casual wear, 5” and 7” shorts are great for sports. Your shorts should hit above your knee unless you’re playing around with recent luxury fashion trends.
  • Invest in denim shorts, khaki shorts, and one darker color (navy or black) or one brighter color (blue, salmon, white).
  • A good pair of brown sandals (Rainbows or Birkenstocks) and a good pair of white shoes (Converse, Nike, Puma) are the only two footwears you really need for a summer of shorts.
  • Get tops that have a hemline hitting right at the bottom of the fly of your shorts.
  • Use your shirts to contrast with shorts. Lighter shorts should be paired with darker shirts, and darker shorts should get lighter shirts.

All of the rules were made to be broken. Once you know the basics, venture into monochrome combinations and harsher contrasts! Make this summer the season that you do shorts right.

About the Author: Ben Martin

Ben Martin is a contributing writer for Gemsman with a taste for good vibes and a heart for searching out the mysteries of life. He specializes in philosophy, humorous banter, and overanalyzing pop music. Often found typing during sunrise and skating during sunset