Shorts can be divisive. Some men live in them despite freezing temperatures. Others, like famed menswear designer Nicolas Gabard, refuse to wear them. In fact, there’s an entire subculture of men who won’t wear shorts at all. For some, it’s a fear they will look too casual, too juvenile, or simply not stylish enough. But shorts can be a part of men’s summer fashion. When worn well, shorts can look as polished and intentional as pants. In this guide on how to style men’s shorts, we’ll walk through fit, fabric, and styling tips to help you confidently wear them.
Fit Comes First: Avoid Sloppy Silhouettes
You’ve probably seen photos of Adam Sandler on the red carpet, rocking massive gym shorts that make him look like he’s in the NBA in the mid-2000s. This look works for Adam Sandler because he’s in the midst of a two-decades-long campaign to craft an I-don’t-care-about-conventional-style aura. If you’re not Adam Sandler, we recommend a different approach to shorts.
The measurements are important. If the inseam is too long, the proportions get clunky. If it’s too short and the leg is wide, it can feel awkward. Aim for a tailored shape that sits cleanly at the waist. Common inseam lengths range from 5″-9″ above the knee—long enough to feel grown-up, short enough to avoid bulk. If you have wider legs, you can get away with a wider leg opening; if you have skinnier legs, you might want something more tapered. It’s also good to give thought to the entire silhouette of an outfit. Short shorts are enjoying a renaissance, and we like a nice 5″ or 6″ inseam. While there’s no rule, if you go for something shorter, it’s worth considering the length of the shirt. Something that’s extra long and covers up a lot of the shorts can look awkward.
Context Matters: From Beach to Dinner Table
If you’re confident and have a good eye for styling, you can make any short work in any setting. But not everyone knows how to make swim trunks work away from the pool. A safer strategy: invest in elevated shorts that work in the most relaxed settings (poolside) to more polished settings (brunch at a beach club). Chino-styled shorts in classic colors (navy, beige, grey, sand, etc.) are always a safe bet. They are easy to pair with tees, long-sleeve button-ups, Hawaiian shirts, sweaters, and tanks, conveying a polished and thoughtful feel. Drawstrings are considered more casual. In a laid-back setting, they’re great. But even the right drawstring shorts can look elevated. A t-shirt tucked in creates a clean break. A tasteful untucked button-up shirt covers the drawstring, making them feel less casual.
Fabric Makes the Difference: Choosing the Right Materials for Summer Shorts
Breathable fabrics are a hallmark of modern men’s summer fashion, and shorts are no exception. Natural fibers like linen and cotton are go-to choices for their breathability and lightweight feel, especially in humid climates. Linen offers a laid-back, airy drape that pairs well with tailored tops, while cotton twill has more structure and polish, making it ideal for occasions where you want a more crisp look.
Texture, pattern, and comfort-enhancing flexibility give shorts another dimension beyond the material. Seersucker offers a puckered texture that’s both breathable and visually intriguing; jacquard’s unique weave creates beautifully complex patterns; stretch-blends provide comfort for more active days. Use these materials to add dimension to your look without sacrificing comfort or function. If you’re unsure where to begin, explore some of our thoughts on fabric and fit in our Summer 2025 Menswear Trends post.
Men’s Shorts Outfit Ideas: From Dressier Moments to Casual Days
- Relaxed but Polished – Pair cotton twill shorts with an untucked Oxford shirt and loafers. Add a lightweight jacket if the weather calls for it. Since pants and short-sleeve shirts are a more popular pairing, the reverse (shorts with a long-sleeve) creates a less-common-yet-balanced look.
- Textured & Patterned – Try a jacquard or patterned short with a solid linen shirt and leather sandals. This is a great way to create dimension without going overboard. Textured fabrics create visual intrigue, offering an easy way to give an outfit depth.
- Smart Casual – Combine shorts with a knit polo and suede loafers for a look that could handle a dinner reservation.
- Dress It Down – Swap out the polo or dress shirt for a Hawaiian pattern camp collar shirt. Give it more depth by layering it over a knit tank.
How to Style Men’s Shorts Like You Style Trousers
One approach to styling men’s shorts is to treat them like a core piece of your outfit, not an afterthought. While not universal, there are plenty of looks where you can treat your shorts like pants. When it comes to men’s summer fashion, bring the same mindset you would to the formality of an outfit with pants. In other words, if you want a more relaxed look, skip tucking in your pants. But don’t be afraid to tuck your shirt in with shorts. Doing so creates a nice break in the overall look. A belt can help emphasize that break, but a belt-less look can also add a sense of intentionality to the final outfit.
Final Thoughts on Men’s Summer Shorts Style
Men’s summer fashion doesn’t have to feel restrictive. And shorts shouldn’t be limited to a functional garment that lets the bottom halves of your legs breathe. Styled well, you can create an elegant silhouette and explore the idea of balance. Well-constructed, well-fitted shorts—paired with the right shirts and accessories—can result in some of the most stylish outfits you’ll wear all summer.
Looking for more style advice for the summer? We break down similar warm-weather outfit strategies in What to Pack for Europe in Summer and Warm-Weather Vacation Outfits.
If, after all that, you’re still wondering how to style men’s shorts, the fashion blogger Style Girlfriend wrote a guide to men’s shorts and men’s summer fashion.