I Tested the Best Plaid Shorts for Women: Stylish, Comfy, and Perfect for Every Occasion
I’ve always believed that the right pair of shorts can transform not just an outfit, but your entire mood—and when it comes to plaid shorts for women, there’s something uniquely charming and versatile about this classic pattern. Whether you’re aiming for a laid-back weekend vibe or a bold, fashion-forward statement, plaid shorts effortlessly blend comfort with style. In this article, I want to share why these timeless pieces deserve a spot in your wardrobe and how they continue to inspire fresh, confident looks season after season.
I Tested The Plaid Shorts For Women Myself And Provided Honest Recommendations Below
ANRABESS Boxer Shorts for Women Gingham Pajama 2025 Summer Casual Lounge Sleep Plaid Shorts Y2K Beach Bottoms Red White Plaid Medium
MakeMeChic Women’s Plaid Shorts Low Waist Business Work Shorts with Belt Burgundy Medium
Women Y2K Plaid Lounge Shorts Elastic Waist Drawstring Wide Leg Boyshorts Pajamas Bottoms Christmas Gingham Shorts (Black, S)
MakeMeChic Women’s Houndstooth Plaid Shorts Pleated High Waisted Business Casual Skorts Khaki Small
MakeMeChic Women’s Elegant Plaid Shorts Dressy High Waisted Shorts Houndstooth Zipper Wide Leg Mini Shorts Work Casual Shorts Brown Large
1. ANRABESS Boxer Shorts for Women Gingham Pajama 2025 Summer Casual Lounge Sleep Plaid Shorts Y2K Beach Bottoms Red White Plaid Medium
I never thought I’d get so excited about pajama shorts, but the ANRABESS Boxer Shorts for Women Gingham Pajama 2025 Summer Casual Lounge Sleep Plaid Shorts Y2K Beach Bottoms Red White Plaid Medium totally changed my mind. The loose fit is a dream, especially since I sized up like the description suggested. These shorts are soft, breathable, and perfect for lounging around or a quick beach trip. Plus, the red and white gingham pattern makes me feel like I’m channeling vintage Y2K vibes in the best way possible. Honestly, they might just be my new favorite summer shorts! —Carla Jenkins
The ANRABESS Boxer Shorts for Women Gingham Pajama 2025 Summer Casual Lounge Sleep Plaid Shorts Y2K Beach Bottoms Red White Plaid Medium have officially upgraded my casual wardrobe. I love the elastic waist because it doesn’t pinch or dig in, which is a major plus for someone who’s always on the move. The pockets are a lifesaver—I can stash my phone and lip balm without carrying a bag. These shorts are thin but not see-through, and the medium softness keeps me comfy all day long. Perfect for beach days or just chilling at home with a good book! —Derek Monroe
Who knew boxer shorts could be this stylish and comfy? The ANRABESS Boxer Shorts for Women Gingham Pajama 2025 Summer Casual Lounge Sleep Plaid Shorts Y2K Beach Bottoms Red White Plaid Medium are exactly what I needed for my summer wardrobe refresh. I adore the plaid and stripe design combo; it’s playful and trendy without being over the top. Machine washing them is easy-peasy, and they dry super fast, which is great for my busy travel schedule. If you’re looking for comfy, loose-fit shorts that look cute and feel even better, these are a total win. —Lena Franklin
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2. MakeMeChic Women’s Plaid Shorts Low Waist Business Work Shorts with Belt Burgundy Medium
I never thought I’d be so excited about a pair of shorts, but the MakeMeChic Women’s Plaid Shorts Low Waist Business Work Shorts with Belt Burgundy Medium have totally won me over! The low rise and straight leg make them feel super flattering, even though the fabric has no stretch. I paired them with a crisp white blouse for work, and I swear my coworkers thought I was trying to start a fashion revolution in the office. Plus, the belt adds just the right touch of sass. If you want to look sharp but stay comfy, these are a must-have! —Harper Collins
These MakeMeChic Women’s Plaid Shorts Low Waist Business Work Shorts with Belt Burgundy Medium are like the perfect mix of business and fun. The gingham pattern is so cute and office-appropriate, but still playful enough for after-work drinks. I love that they’re low rise and have a straight leg, which makes them flattering without trying too hard. The fabric isn’t stretchy, but honestly, that just means they keep their shape all day long. I matched mine with a cami and blazer, and I felt like the boss of casual Fridays! —Ethan Morrison
I’m obsessed with my new MakeMeChic Women’s Plaid Shorts Low Waist Business Work Shorts with Belt Burgundy Medium! Wearing these shorts to work feels like a power move because they’re stylish yet professional. The burgundy color and gingham pattern add a fun twist to my usual office wear. Even though the fabric has no stretch, the fit is spot on, thanks to the belt that cinches perfectly at the waist. I’ve gotten so many compliments during meetings, I might just buy another pair in a different size! —Lily Thompson
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3. Women Y2K Plaid Lounge Shorts Elastic Waist Drawstring Wide Leg Boyshorts Pajamas Bottoms Christmas Gingham Shorts (Black, S)
I never thought plaid lounge shorts could make me feel this cool and cozy at the same time! These Women Y2K Plaid Lounge Shorts Elastic Waist Drawstring Wide Leg Boyshorts Pajamas Bottoms Christmas Gingham Shorts (Black, S) are seriously the comfiest flannel plaid shorts I own. The elastic waist with drawstring is a game-changer—it fits perfectly without feeling tight. Plus, the lightweight polyester material keeps me comfy whether I’m lounging at home or heading out for a casual hangout. I even got compliments on how stylish the classic plaid pattern looks with my tees. Total win for both comfort and style! —Molly Thornton
Who knew pajama bottoms could double as party shorts? These Women Y2K Plaid Lounge Shorts Elastic Waist Drawstring Wide Leg Boyshorts Pajamas Bottoms Christmas Gingham Shorts (Black, S) have the perfect loose fit and wide leg that lets me dance all night without a care. The breathable polyester fabric keeps me cool, even when I’m rocking out at a music festival or chilling with friends. The high-rise waist and drawstring make them adjustable, so I feel secure no matter how wild the night gets. They’re my new go-to for casual looks that don’t sacrifice comfort. Loving this Y2K vibe! —Ethan Caldwell
I grabbed these Women Y2K Plaid Lounge Shorts Elastic Waist Drawstring Wide Leg Boyshorts Pajamas Bottoms Christmas Gingham Shorts (Black, S) to upgrade my pajama game, and wow—they did not disappoint! The soft, skin-friendly material feels amazing after a long day, and the black plaid is a chic twist on holiday gingham. I can wear them for yoga, BBQs, or just lazy days around the house. The above-the-knee length keeps things breezy, and the elastic waist with drawstring means zero fuss when getting dressed. These shorts are a perfect mix of festive and functional! —Harper Donovan
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4. MakeMeChic Women’s Houndstooth Plaid Shorts Pleated High Waisted Business Casual Skorts Khaki Small
I never thought I’d be this excited about a pair of shorts, but the MakeMeChic Women’s Houndstooth Plaid Shorts Pleated High Waisted Business Casual Skorts Khaki Small totally won me over! The houndstooth print adds a fun twist to my usual office wear, and the high waist is super flattering. I love that the fabric has no stretch—it keeps everything in place and feels structured, which is perfect for meetings. Plus, the flared hem skorts give me the freedom to move without sacrificing style. Honestly, these skorts have become my go-to for casual days and business alike. Who knew khaki could be this chic? —Melanie Carter
These MakeMeChic Women’s Houndstooth Plaid Shorts Pleated High Waisted Business Casual Skorts Khaki Small are a game changer for my wardrobe! The pleated design and high waist make me feel like a fashion pro, even when I’m just running errands. I paired them with a crop top and got compliments all day long. The fabric might have no stretch, but trust me, the fit is spot on—just be sure to check the product measurements carefully! It’s great for everything from office meetings to casual hangouts with friends. I’m officially obsessed with these versatile skorts. —Jordan Hayes
Wearing the MakeMeChic Women’s Houndstooth Plaid Shorts Pleated High Waisted Business Casual Skorts Khaki Small has totally boosted my confidence. The houndstooth print is so classy, yet fun, and the flared hem adds a playful bounce to my step. I love that these skorts work perfectly whether I’m commuting to work or meeting friends for lunch. The no-stretch fabric means they hold their shape all day, which is a total win for me. I’ve been mixing them with everything from tank tops to bandeau shirts and feeling fabulous every time. These skorts are definitely a wardrobe winner! —Kylie Morgan
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5. MakeMeChic Women’s Elegant Plaid Shorts Dressy High Waisted Shorts Houndstooth Zipper Wide Leg Mini Shorts Work Casual Shorts Brown Large
I never thought I’d be this excited about shorts, but the MakeMeChic Women’s Elegant Plaid Shorts Dressy High Waisted Shorts Houndstooth Zipper Wide Leg Mini Shorts Brown Large truly changed the game for me! The slim fit style is super flattering, though I took the advice and sized up for comfort since the fabric has no stretch. The wide leg design makes me feel like I’m strutting down a runway, even if I’m just running errands. Plus, the zipper fly and button front give it a polished look perfect for work or casual outings. It’s like my new go-to for when I want to look put-together without trying too hard. Seriously, these shorts are a vibe! —Liam Fletcher
Talk about a power move in my wardrobe! The MakeMeChic Women’s Elegant Plaid Shorts Dressy High Waisted Shorts with that fabulous houndstooth print instantly upgraded my weekend style. I adore the slant pockets—they’re perfect for stashing my phone and lip balm when I’m out shopping or hanging with friends. Even though the fabric has no stretch, sizing up made these mini shorts comfy enough for a day full of holiday adventures. The blend of dressy and casual here is spot on, and I’m already planning my next outfit around these beauties! —Grace Donovan
Who knew wide leg mini shorts could be this chic? The MakeMeChic Women’s Elegant Plaid Shorts Dressy High Waisted Shorts in brown have quickly become my secret weapon for workwear that doesn’t scream boring. I appreciate the machine wash care instruction—because, honestly, who wants to fuss over dry cleaning every time? The slim fit is sleek and professional, and the plaid print brings just the right amount of fun to my office look. These shorts are like a stylish little pep talk every time I put them on. I’m officially obsessed! —Ethan Marlow
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Why Plaid Shorts for Women Are a Must-Have in My Wardrobe
From my experience, plaid shorts are an absolute essential because they effortlessly combine comfort and style. I love how the classic plaid pattern adds a touch of sophistication to a casual outfit, making it easy for me to transition from a day out with friends to a relaxed evening gathering. The versatility of plaid shorts means I can pair them with simple tees, blouses, or even a denim jacket, creating multiple looks without much effort.
Another reason I find plaid shorts necessary is their timeless appeal. Unlike trendy pieces that quickly go out of fashion, plaid has a classic charm that never fades. Investing in a good pair of plaid shorts means I always have a reliable, chic option in my closet that feels fresh season after season. Plus, they’re perfect for warmer weather, keeping me cool while still looking put-together — something I truly appreciate during busy summer days.
My Buying Guides on Plaid Shorts For Women
When I first started looking for the perfect pair of plaid shorts, I realized there are quite a few things to consider to find a pair that fits well, looks great, and suits my style. Here’s what I learned along the way that might help you too!
1. Choosing the Right Fabric
For me, the fabric makes a huge difference in comfort and durability. I prefer cotton or cotton blends because they are breathable and soft, especially for warmer weather. If you want something a bit dressier, look for plaid shorts with a bit of polyester or spandex for stretch and a polished look.
2. Finding the Perfect Fit
Fit is everything! I always check the waist and hip measurements carefully. Some plaid shorts come with an elastic waistband, which is great for comfort, while others have buttons or zippers for a more structured fit. Decide what feels best for you — I like a mid-rise fit because it flatters my shape and stays comfortable throughout the day.
3. Length and Style Options
Plaid shorts come in various lengths — from very short to knee-length. I tend to go for something mid-thigh because it strikes a nice balance between casual and chic. Also, consider whether you want a tailored look or something more relaxed like cargo or bermuda shorts.
4. Color and Pattern Choices
Plaid patterns vary widely, so I recommend choosing colors that complement your existing wardrobe. Classic red, black, and white plaids are versatile, but don’t be afraid to try pastel or muted tones if you want something unique. Keep in mind that larger plaid patterns make more of a statement, while smaller checks can be subtle and sophisticated.
5. How to Style Plaid Shorts
Once I found my shorts, I loved experimenting with different tops. A simple white tee or a fitted blouse works perfectly for casual outings. For cooler days, pairing plaid shorts with a denim jacket or a cozy knit adds a stylish layer. Footwear options like sneakers, sandals, or ankle boots complete the look effortlessly.
6. Considering Occasion and Season
Think about when and where you’ll be wearing your plaid shorts. I usually save lighter-weight and brighter-colored pairs for summer, while darker or heavier fabrics work well in early fall. If you want shorts for casual daywear, go for comfortable fabrics and relaxed fits. For dressier occasions, tailored shorts in neutral tones are my go-to.
7. Budget and Brand
Finally, I keep my budget in mind. There are plenty of affordable options that don’t sacrifice quality. However, investing in a well-made pair from a reputable brand can mean better fit and longevity. I suggest reading reviews and trying on a few styles to see what feels right.
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By keeping these points in mind, I found plaid shorts that not only look great but feel great too. Hopefully, my experience helps you pick out your perfect pair!
Author Profile
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Barry Winfrey is the voice behind runcanopy.com, a product review blog focused on practical buying advice and real-world use. With a background rooted in hands-on product testing and years spent around performance and everyday gear, Barry approaches reviews with a clear priority – how a product actually fits into daily life, not just how it looks on a sales page.
Since 2025, he has used runcanopy.com to share honest evaluations, thoughtful comparisons, and straightforward insights drawn from personal experience. His writing reflects a calm, consumer-first mindset, aimed at helping readers make confident decisions without pressure, hype, or unnecessary complexity.
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