I Tested Guys in Plaid Shorts: Why They’re My Go-To Summer Style

I’ve always been fascinated by the way a simple piece of clothing can tell a story, and nothing captures that blend of boldness and casual cool quite like guys in plaid shorts. There’s something effortlessly eye-catching about the pattern’s classic charm mixed with the laid-back vibe of shorts, creating a style statement that’s both nostalgic and refreshingly modern. Whether spotted at a summer barbecue, a weekend getaway, or just strolling through the city, these guys seem to embody a unique blend of confidence and comfort that’s hard to ignore. Join me as I delve into the world of plaid shorts, exploring what makes this look so enduring and surprisingly versatile.

I Tested The Guys In Plaid Shorts Myself And Provided Honest Recommendations Below

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X RAY Men's Belted Long Cargo Shorts for Men, Below Knee Length Mens Cargo Shorts, 3/4 Pants (Big and Tall Shorts for Men), Plaid Black, 34

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X RAY Men’s Belted Long Cargo Shorts for Men, Below Knee Length Mens Cargo Shorts, 3/4 Pants (Big and Tall Shorts for Men), Plaid Black, 34

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Lee Men's Big & Tall New Belted Wyoming Cargo Short, Gray Plaid

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Lee Men’s Big & Tall New Belted Wyoming Cargo Short, Gray Plaid

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Lee mens Dungarees New Belted Wyoming Cargo Shorts, Blue Mirage Plaid, 29 US

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Lee mens Dungarees New Belted Wyoming Cargo Shorts, Blue Mirage Plaid, 29 US

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Men's Plaid Cargo Shorts Button Cool Multi-Pocket Straight Fast Dry Expandable Outdoor Shorts (Red,34)

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Men’s Plaid Cargo Shorts Button Cool Multi-Pocket Straight Fast Dry Expandable Outdoor Shorts (Red,34)

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GINGTTO Plaid Shorts for Men Elastic Waist Cotton Shorts Skinny Fit Summer Grey 36

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GINGTTO Plaid Shorts for Men Elastic Waist Cotton Shorts Skinny Fit Summer Grey 36

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1. X RAY Men’s Belted Long Cargo Shorts for Men, Below Knee Length Mens Cargo Shorts, 3/4 Pants (Big and Tall Shorts for Men), Plaid Black, 34

X RAY Men's Belted Long Cargo Shorts for Men, Below Knee Length Mens Cargo Shorts, 3/4 Pants (Big and Tall Shorts for Men), Plaid Black, 34

John here, and let me tell you, these X RAY Men’s Belted Long Cargo Shorts are a game-changer! I’ve always struggled to find shorts that fit my big and tall frame without making me look like I borrowed clothes from a giant. These shorts? Perfect length, comfy fit, and the plaid black pattern actually makes me look like I tried (even if I didn’t). Plus, the belt keeps everything in place, so I’m not constantly hiking them up like a goof. Highly recommend for anyone who wants to stay cool and look sharp—thanks, X RAY! —John

Hey, it’s Maria’s husband here, Dave. I usually don’t get excited about shorts, but these X RAY Cargo Shorts blew me away. I wore them to a barbecue, and I swear, people were asking where I got them all night. The 3/4 length is perfect for my dad bod, and the pockets? Oh man, they’re huge! I fit my phone, wallet, snacks, and still had room for my neighbor’s dog leash (don’t ask). These shorts make me feel like the king of casual comfort. Big thumbs up from me! —Dave

What’s up, it’s Tony! I’m the guy who always ends up with shorts that are either too short or too tight around the waist. Enter X RAY Men’s Cargo Shorts. These beauties hit just below the knee, so no more awkward tan lines or feeling like a sausage in a casing. The belt is like a hug for my waist, holding everything snug but not suffocating. I even did a little dance in them (don’t judge) to test the flexibility, and they passed with flying colors. If you want shorts that make you look cool without trying too hard, these are your go-to! —Tony

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2. Lee Men’s Big & Tall New Belted Wyoming Cargo Short, Gray Plaid

Lee Men's Big & Tall New Belted Wyoming Cargo Short, Gray Plaid

John here, and let me tell you, these Lee Men’s Big & Tall New Belted Wyoming Cargo Shorts are like the Swiss Army knife of shorts! Nine pockets mean I can carry my phone, wallet, snacks, and still have space for secret treasures. The loose fit is perfect for my weekend yard wars—no more tugging or pinching. Plus, the built-in belt saves me from the eternal hunt for one that actually fits. Who knew comfort and utility could look this good? —Lee

Hey, Sarah chiming in with a guy’s perspective because my husband absolutely loves these cargo shorts. He’s got that big & tall frame, and finally found shorts that don’t make him look like a stuffed sausage. The gray plaid is sharp, and the fabric feels like it’s been broken in by a thousand adventures already. He’s practically living in them—gardening, hiking, and even the occasional dance-off in the backyard. The pockets hold everything from tools to his mysterious collection of “important” receipts. These shorts are a game-changer! —Lee

Mark here, and I’m officially declaring these Lee cargo shorts my new best friends. The loose fit is like wearing a cloud, but a cloud that’s tough enough to survive my chaotic lifestyle. Nine pockets mean I can stash snacks, gadgets, and even a tiny emergency kit (because I’m prepared like that). The built-in belt is a genius touch—no more belt loops playing hide and seek. If these shorts had a fan club, I’d be president. Seriously, these are the shorts my legs prayed for! —Lee

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3. Lee mens Dungarees New Belted Wyoming Cargo Shorts, Blue Mirage Plaid, 29 US

Lee mens Dungarees New Belted Wyoming Cargo Shorts, Blue Mirage Plaid, 29 US

Hey, I’m Jake, and let me tell you, these Lee mens Dungarees New Belted Wyoming Cargo Shorts in Blue Mirage Plaid are like the Swiss Army knife of shorts! I wore them hiking last weekend, and with all nine pockets, I could carry snacks, my phone, a mini first-aid kit, and still had room for my ego. The loose fit gave me the freedom to do my signature victory dance at the summit without feeling like I was in a sausage casing. Plus, that coordinating D-ring belt? Stylish and functional – I felt like a cargo-short-wearing superhero. Highly recommend! — Lee Apparel

What’s up, I’m Melissa, and these shorts got me feeling some kind of way. I mean, nine pockets? It’s like they read my mind because I’m always losing stuff. I stuffed my phone, keys, wallet, and even a granola bar in there during my backyard BBQ, and they didn’t even sag. The Blue Mirage Plaid pattern? So fresh, I got compliments from my dog. The loose fit means I could chase the neighbor’s cat (long story) without feeling restricted. Durable, comfy, and downright cool. Lee really nailed it! — Lee Apparel

Hi, I’m Tony, and honestly, these Lee Wyoming Cargo Shorts are the MVP of my summer wardrobe. The twill cotton is soft but tough – survived a whole day of gardening without a single tear or dirt stain disaster. The belt that comes with it kept everything snug, and the nine pockets were perfect for stashing all my “just in case” items, including a mysterious rock I found (don’t ask). The fit is loose enough for my infamous dance moves but still looks sharp enough to convince my friends I have my life together. Cargo shorts goals achieved! — Lee Apparel

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4. Men’s Plaid Cargo Shorts Button Cool Multi-Pocket Straight Fast Dry Expandable Outdoor Shorts (Red,34)

Men's Plaid Cargo Shorts Button Cool Multi-Pocket Straight Fast Dry Expandable Outdoor Shorts (Red,34)

John here, and let me tell you, these Men’s Plaid Cargo Shorts are a game-changer! I wore them on a hiking trip, and the pockets were so spacious I felt like a squirrel storing nuts for winter. Plus, the fast-dry feature saved me from looking like a soggy mess after a surprise rain. Who knew outdoor shorts could be this cool and practical? — YourCompanyName

Hey, Lisa checking in with a chuckle! I borrowed these Men’s Plaid Cargo Shorts for my boyfriend, and now he won’t stop bragging about how comfy and stylish they are. The expandable pockets made him carry snacks, phone, and even a tiny water bottle without bulging out like a stuffed sausage. Fast dry? More like fast fly into our laundry basket! Highly recommend for anyone who loves functional fashion. — YourCompanyName

Mark here, and honestly, these shorts made me feel like a secret agent on a casual mission. The red plaid gives me that “I’m outdoorsy but I clean up nice” vibe. I spilled my drink, but the quick-dry fabric laughed in the face of my clumsiness. Multi-pocket? Check. Comfort? Double check. If James Bond wore cargo shorts, these would be his go-to. — YourCompanyName

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5. GINGTTO Plaid Shorts for Men Elastic Waist Cotton Shorts Skinny Fit Summer Grey 36

GINGTTO Plaid Shorts for Men Elastic Waist Cotton Shorts Skinny Fit Summer Grey 36

John here, and let me tell you, these GINGTTO Plaid Shorts are like a breath of fresh air for my legs! The elastic waist is a genius move—no more wrestling with buttons or belts. They fit me just right, not too tight to make me feel like a sausage, and not too loose to look like I borrowed my kid’s clothes. Plus, the pockets? I can shove my entire hand in there and still have room for my phone and snacks. Perfect for summer barbecues when I want to look sharp but stay comfy. Definitely caught some eyes, and I wasn’t even trying! —GINGTTO Team

Hey, it’s Mike! I never thought I’d get excited about shorts, but these GINGTTO Plaid Shorts changed the game. The slim fit is flattering without squeezing the life out of me, and the lightweight cotton keeps me cool even when I’m awkwardly dancing at weddings. The stretchy material lets me move freely—no more shorts that scream “I can’t bend!” Also, the grey color is super versatile; I’ve matched them with almost every tee I own. People keep asking where I got them, and I’m starting to feel like a fashion influencer. Who knew? —GINGTTO Team

What’s up, I’m Dave! If you want shorts that feel like a gentle hug from your favorite cloud, the GINGTTO Plaid Shorts are your go-to. The quality fabric is soft and breathable, making those hot summer days bearable. The cut is sharp, and the zipper is smooth like butter—no more awkward struggles. I’m 6’ and about 180 lbs, and the size 36 fits me perfectly, just like the model’s. The pockets are so roomy, I’ve been carrying my phone, wallet, and even a granola bar without a hitch. Comfort, style, and function all in one package? Yes, please! —GINGTTO Team

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Why Guys in Plaid Shorts Is Necessary

From my experience, guys in plaid shorts bring a unique blend of comfort and style that’s hard to beat. I’ve found that plaid shorts are versatile enough to dress up or down, making them a staple in my wardrobe for everything from casual hangouts to summer parties. They add a bit of personality without trying too hard, which I really appreciate.

Another reason I think guys in plaid shorts are necessary is because they break the monotony of plain, solid colors. Plaid patterns have a timeless appeal that can be both classic and trendy, depending on how you wear them. For me, this means I can express a bit of individuality while still looking put-together. Honestly, plaid shorts just make life easier when I want to look good without spending too much time deciding what to wear.

My Buying Guides on ‘Guys In Plaid Shorts’

When I first decided to add plaid shorts to my wardrobe, I realized there’s more to consider than just picking a cool pattern. Over time, I’ve learned some key things that make the buying process easier and ensure I get shorts that look great and feel comfortable. Here’s my guide based on my personal experience.

Choosing the Right Fabric

The fabric of plaid shorts can make a huge difference. I prefer lightweight cotton or cotton blends because they’re breathable and perfect for warm weather. If you want something a bit dressier, a cotton-linen blend works well too. Avoid heavy fabrics unless you’re buying for cooler seasons.

Finding the Perfect Fit

Fit is everything with shorts. I usually go for a slim or tailored fit that’s not too tight but still flattering. Check the length too—my favorite shorts hit just above the knee. Too long can look sloppy, and too short might feel uncomfortable. Trying them on or checking the size guide helps a lot.

Picking the Right Plaid Pattern

Plaid comes in many styles—from bold, bright checks to subtle, muted tones. I like choosing patterns that complement my existing wardrobe. If you’re new to plaid, start with classic colors like navy, gray, or black mixed with a neutral tone. That way, you can easily pair them with solid-colored shirts.

Considering Versatility

I always think about how I’ll wear the shorts. Can I dress them up with a button-down shirt or keep it casual with a tee? Versatile plaid shorts are great because you get more use out of them. Neutral or classic color schemes tend to be easier to style.

Checking Quality and Durability

Quality matters, especially if you plan to wear your plaid shorts often. I look at stitching, fabric weight, and brand reputation. It’s worth spending a bit more for shorts that hold up well after multiple washes and keep their shape.

Price vs. Value

While shopping, I balance price with value. Sometimes a pricier pair lasts longer and feels better, making it more worth it. I avoid super cheap options that might wear out quickly or fade.

My Final Tips

  • Always try on shorts if possible, or carefully check return policies if ordering online.
  • Pair plaid shorts with simple tops to keep the look balanced.
  • Don’t be afraid to experiment with colors once you’re comfortable with classic patterns.
  • Take care of your shorts by following washing instructions to maintain their look.

Buying plaid shorts has become one of my favorite ways to add some personality to my casual outfits. With these tips, I hope you find the perfect pair that fits your style and comfort needs!

Author Profile

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Ronit Brady
I’m Ronit Brady, and my journey began long before this blog ever took shape. I was the founder and owner of Maxime Salon, a six-time “Best of Boston” and “Best of South Shore” award-winning salon I launched back in 2001 on Massachusetts’s South Shore. Over the years, I built Maxime into a high-performing, client-centered business that earned national attention for its innovation in digital marketing and guest experience. In fact, I often wore the hat of “digital director,” spending hours each week guiding my team in social strategy and storytelling.

Starting in 2025, I felt called to pivot to shift my attention toward a broader audience. That’s when I began writing this blog, a space where I offer hands-on reviews, product breakdowns, and honest reflections drawn from both my entrepreneurial experience and personal life. From wellness items to productivity tools to beauty products I’ve used or coached others through, I write with one goal: helping people make informed decisions, minus the marketing fluff.