Summer is for short shorts. If you’re not sure how to style short shorts for men, we’re guiding you through the basics.
Skies out, thighs out, right? In a world where pants keep getting bigger, shorts go the opposite direction.
Letting your thighs out to breathe feels risque, but it’s actually not totally new to men’s fashion. In fact, short shorts are rooted in 70’s and 80’s fashion.
In this guide, we’ll introduce you to short shorts and show you how to effortlessly style them. By the end of this, you’ll feel confident rocking out with your thighs out.
A Brief History of Men’s Shorts
British soldiers wore shorts in World War 1. Shorts were born out of military uniforms cut to length due to heat.
In the 19th and 20th centuries, shorts (or knickerbockers) were mainly reserved for young boys. Outside of sports, men wouldn’t wear shorts because they were considered particularly immature and casual. Overall, shorts were donned out of necessity and on very rare occasions.
What Is a Short Short?
Everyone has their comfort level when it comes to how much thigh they’re willing to expose in a pair of shorts.
For some, any shorts with inseams shorter than 9” feel pretty cropped. For the average guy, 9” hits right around or just past the knee. For the record, the average height in the US is right around 5’9”.
However, shorts with 7” inseams are fairly average and mainstream nowadays. That inseam hits right above the knee. If you’re a true short-shorts aficionado, a 5” inseam is the true benchmark. That length hits right around mid-thigh.
For this guide, we’ll call anything shorter than 7” a true short-short. Anything over 9” might as well be a capris pant.
How Men’s Shorts Should Fit
The way your shorts should fit is completely dependent upon how comfortable you feel, showing some extra leg. Still, there are a few other things to think about in terms of fit.
Tapered shorts with slim leg openings will feel tight in the thigh. If they’re too tight, they restrict mobility. This usually happens with cut-off or DIY shorts.
Quite frankly, a tight short-short isn’t flattering.
Your shorts should be easy to move in. Comfort is a top priority for casual clothing items.
A straight or a-line fit is the most flattering cut for most guys. A straight fit, just like pants, means no taper in the leg.
An A-line fit means that the leg opening gets slightly wider at the bottom of the shorts. A-line fits are particularly flattering when you’re pairing them with a structured top (think little shirt, big pants).
The actual length of your shorts is a matter of preference. Since this is a short-shorts guide, stick to inseams that are at least 2” above your knees to get your desired look.
Shorter guys can go even shorter to show off more leg. It actually balances you out and makes you appear taller. If you’re proud of your legs, show them off!
When To Wear Short-Shorts
All shorts are inherently casual. Unless you live in Burmuda, don’t plan on wearing them to any formal events.
The shorter you go, the more casual the shorts become. Reserve shorts for your casual daytime events, outings, or errands.
There are a few different types of shorts to consider as well.
Running and athletic shorts come in very short inseams. While they can be styled outside of the gym and sports, it’s also important to have shorts that aren’t made out of sports fabrics.
Balance your casual wardrobe with higher quality materials like cotton and linen blends as well.
How To Wear Short-Shorts
You’ll see that styling short shorts isn’t hard. It’s about your comfort level in them and balancing out the rest of your outfit. This will give you several options.
Tee and Short Shorts
Start simple. Pair short shorts with any tee shirt you already own. There’s no special trick to styling short shorts; you can just start.
Stick to structured tees that aren’t too long. An untucked shirt that extends beyond your shorts will look a little wonky. Try tucking in the tee to create more structure.
Substitute a polo here if a shirt feels too boring. Polos offer nice added detail and pair well with shorts, too.
Tank Top and Short Shorts
It’s the ultimate summer uniform. While it seems simple, there’s a lot you can do with just a tank and a pair of shorts. This allows you to experiment with different styles of tanks and different styles of shorts.
These shorts aren’t the shortest, but they had room to pull up on the waist. That reveals more leg and creates a shorter look. Feel free to do that with shorts you already own.
Tighter-fitting tanks with wide-leg shorts look totally different than a loose tank and straight-legged shorts. Accessories also add more personality to simple outfits like this.
Button Downs and Short Shorts
A little light layering goes a long way.
Throw a short-sleeve or long-sleeve shirt over a tank or tee with your short shorts, and you create a slightly layered look. Or experiment with different tuck styles.
Doing a half tuck or a front tuck adds structure. It’s a fun way to compliment short shorts and create a new look.
Sweater Polos and Short Shorts
Sweater polos are the rage right now. The added texture and higher quality elevate a short-shorts outfit. They are also great for light layering.
Button-down knit polos are the best for this. You can wear them like a button-down shirt or like a traditional polo, depending on what you feel most comfortable in.
Long Sleeves, Short Shorts
This is my favorite combo, and Spring feels like the best season for it. You can pair your light sweaters with your short shorts.
The two balance themselves out. The fabric you’re missing on your legs shows up on your arms. Well, not actually, but you get the point.
It also helps you look taller (the short shorts) and broader in your shoulders (push up your sleeves).
Patterned Short Shorts
Short shorts are a great excuse to experiment with bold patterns. Because they take up such little real estate, go for bigger and bolder pops.
These look great with solid color tees, tanks, or any other tops. If you’re not sold on short shorts yet, try a fun pair that you can break out when the warm weather hits.
Patterned sets with short shorts are great to experiment with as well. The shorts are short, but the overall pattern creates unity.
Athletic Short Shorts
The 70s and 80s style athletic and basketball short shorts made a comeback. Rather than being decked out in sports lettering and numbers, they have cool designs that make them more fashion-forward.
These ones from Abercrombie are a perfect example. The floral embroidery makes them more interesting than just a pair of retro basketball shorts. But they’re definitely still short!
Short Shorts Swim Trunks
If showing a little extra thigh on the street isn’t your cup of tea, start poolside. Swim trunks typically come in shorter inseams, which makes them great entry points.
You can style them with tanks, button-down shirts, and more while hanging poolside to test your comfort level. They also typically come in brighter colors and patterns, leaving more room for experimentation.
Short Cargo Shorts
These are a new favorite. Even just a few years ago, you wouldn’t see many menswear experts advocating for cargo shorts. Typically, they’re shapeless and unflattering.
Just as the oversized, structured cargo shorts re-entered the scene, so too are short cargo shorts. The key is structure. They can’t be loose or shapeless. The shorter length gives them more structure and makes them worth trying again.
Will You Try Short Shorts?
Are you ready to style short shorts? Remember, short doesn’t have to mean an obscenely tiny inseam. Start with shorts that end about 2” above your knee and test your confidence level.
If you have any questions or comments, leave them down below!
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