Some fashion mistakes are forgivable, but when it comes to men’s shorts, the wrong pair can ruin an otherwise solid outfit. Shorts are tricky—they’re casual by nature, but that doesn’t mean anything goes. The length, fabric, and fit all reveal something about the thought you put into getting dressed. Wearing the wrong shorts can make you look sloppy, dated, or like you’re trying too hard. If you care about style and comfort, it’s worth knowing which ones to leave behind. Here are seven types of shorts men should never be caught wearing.
1. Cargo Shorts with Bulging Pockets
Cargo shorts were once practical, but they’ve become the poster child for lazy dressing. Those oversized pockets make your silhouette bulky and unflattering. Even worse, they sag when stuffed with keys, wallets, and phones, making you look like you’re carrying camping gear to brunch. Streamlined styles with slimmer cuts do the same job without the extra fabric. If you need storage, try a lightweight crossbody bag instead of turning your shorts into a utility belt.
2. Extra-Short Gym Shorts
There’s a fine line between athletic and awkward. The super-short gym shorts some men wear outside the gym cross that line fast. They might work for running laps, but not for grabbing coffee or running errands. The thin material clings, rides up, and leaves little to the imagination. A mid-thigh cut with a structured fabric looks sharper while still keeping you cool. Save the micro lengths for workouts or the beach—anywhere else, they just look like you forgot your pants.
3. Denim Shorts That Look Like Cutoffs Gone Wrong
Distressed denim shorts can easily go from edgy to embarrassing. Jagged hems and random rips might look rebellious in theory, but they often read as careless. If they’re too tight, they highlight all the wrong areas; too baggy, and you look like you’re stuck in a 1990s music video. A cleaner, well-fitted denim short can work, but only in darker washes and tailored shapes. Think polished, not punk.
4. Board Shorts Outside the Beach
Board shorts have a time and place—on the sand, near water, or at a pool party. Anywhere else, they look like you’re lost on your way to surf practice. The shiny, synthetic fabric and long, wide legs make them hard to style with anything other than flip-flops. They also tend to sit low on the hips, which throws off proportions. If you like the relaxed vibe, opt for chino shorts instead. They’re casual but still look intentional. Brands like J.Crew and Bonobos offer versions that work for both weekends and travel.
5. Pleated Shorts That Belong in the Past
Pleated shorts were once a standard in the 1980s, but fashion has since evolved. The extra fabric at the waist adds unnecessary volume, especially if you’re not wearing a tucked-in shirt. They make your midsection look larger and your outfit dated. Flat-front shorts with a clean waistband are the modern alternative. They give you a sharper, more balanced look without adding bulk. If you still have pleated pairs in your closet, it’s time to retire them.
6. Super Long, Baggy Basketball Shorts
Basketball shorts have a comfortable appeal, but when they hang past your knees, they distort your proportions. The baggy fit makes your legs look shorter and throws off the rest of your outfit. They also tend to be made from shiny polyester that clashes with streetwear or casual looks. If you’re looking for sporty comfort, opt for athletic-inspired shorts that hit just above the knee. They maintain a relaxed vibe without appearing sloppy. Wearing them the right length instantly sharpens your silhouette.
7. Novelty or Joke Shorts
Shorts covered in cartoon prints, neon flamingos, or ironic slogans might get laughs, but not for the right reasons. They make you look like you’re stuck in a college dorm phase. Clothing should say something about your style, not your sense of humor at a backyard barbecue. If you want to show personality, do it through color or subtle patterns. A tasteful stripe or earthy tone adds character without crossing into costume territory. The goal is effortless confidence, not attention for the wrong reasons.
Why the Right Shorts Matter
Choosing the right pair of shorts isn’t about following strict fashion rules—it’s about respect for fit and occasion. The best shorts for men balance comfort, proportion, and context. You can still be casual without looking careless. Shorts that flatter your frame and suit your lifestyle send the message that you pay attention to details, even when it’s hot outside.
When you avoid the shorts men should never be caught wearing, you instantly elevate your summer wardrobe. The right choices make transitions from errands to social events effortless. It’s not about being trendy—it’s about looking put-together without trying too hard. So next time you reach for a pair, think about length, fabric, and shape before stepping out the door.
What’s the worst pair of shorts you’ve ever seen someone wear in public?
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