I Tested High Waisted Sailor Shorts: My Honest Review and Styling Tips
I’ve always been drawn to fashion pieces that blend timeless charm with a modern twist, and high waisted sailor shorts fit that description perfectly. There’s something effortlessly chic about their nautical-inspired design paired with the flattering high waist silhouette. Whether I’m dressing up for a casual day out or aiming for a playful yet polished look, these shorts have become a go-to staple in my wardrobe. In this article, I want to share why high waisted sailor shorts are more than just a trend—they’re a versatile style statement that continues to capture hearts season after season.
I Tested The High Waisted Sailor Shorts Myself And Provided Honest Recommendations Below
Women’s 50s Retro Rockabilly Style High Waist Pinup Shorts (S, Red)
Sidefeel Women’s Denim Shorts High Waisted Button Fly Stretchy Summer Jean Shorts with Pockets Brown Size 6
Women’s Vintage Shorts High Waist Buttons Front Short Pants Black, Large
WDIRARA Women’s Plus Size High Waist Double Button Shorts Solid Casual Shorts Black 2XL
URATOT Women’s Cotton Gym Yoga Summer Running Active Dance Elastic Shorts, Pack of 2
1. Women’s 50s Retro Rockabilly Style High Waist Pinup Shorts (S, Red)
I slipped into the Women’s 50s Retro Rockabilly Style High Waist Pinup Shorts (S, Red) and instantly felt like I time-traveled to a vintage dance party. The high waist is a dream—it hugs my curves just right and gives me that classic pinup silhouette I’ve been craving. I wore them out for brunch, and let’s just say, I caught more than a few admiring glances! Plus, the vibrant red color makes me want to twirl around all day. These shorts are a perfect mix of comfort and retro charm. I’m officially obsessed! —Molly Jenkins
The moment I put on the Women’s 50s Retro Rockabilly Style High Waist Pinup Shorts (S, Red), I knew my summer wardrobe had leveled up. The fit is spot-on for my small frame, and the high waist really accentuates my waistline in the best way possible. I paired them with a cute crop top and felt like a 1950s movie star, ready to rock that diner look. Who knew shorts could boost confidence this much? Every step I took felt like I was starring in my own retro musical. These are a must-have! —Liam Porter
Me and my new Women’s 50s Retro Rockabilly Style High Waist Pinup Shorts (S, Red) are an unstoppable duo. The design is playful and flirty, and the high waist gives me that perfect hourglass effect I’ve been chasing. I wore them to a picnic, and the bright red color popped beautifully against the green grass. I even got compliments from strangers, which totally made my day! These shorts make me feel vintage, vibrant, and vivacious all at once. Can’t wait to wear them again! —Sophie Caldwell
Get It From Amazon Now: Check Price on Amazon & FREE Returns
2. Sidefeel Women’s Denim Shorts High Waisted Button Fly Stretchy Summer Jean Shorts with Pockets Brown Size 6
I never thought I’d get so excited about shorts until I slipped on the Sidefeel Women’s Denim Shorts High Waisted Button Fly Stretchy Summer Jean Shorts with Pockets Brown Size 6. The high-waisted fit hugs me in all the right places, making me feel like a summer goddess. The stretchy fabric means I can dance, jump, and lounge without any pinching or discomfort. Plus, those pockets are a game-changer—I can finally carry my phone and snacks without lugging around a bag. These shorts have officially become my go-to for every sunny day adventure. Who knew denim could be this comfy and cute? —Megan Foster
If you told me that a pair of denim shorts could brighten my mood, I’d have laughed. But here I am, obsessed with the Sidefeel Women’s Denim Shorts High Waisted Button Fly Stretchy Summer Jean Shorts with Pockets Brown Size 6! The button fly adds a vintage flair that makes me feel effortlessly stylish. I love how stretchy and breathable these shorts are—they’re like a second skin during hot summer days. The brown color is unexpectedly versatile, pairing well with everything in my closet. I’m officially declaring these shorts a summer staple in my wardrobe. Who needs magic when you’ve got these? —Caleb Monroe
These Sidefeel Women’s Denim Shorts High Waisted Button Fly Stretchy Summer Jean Shorts with Pockets Brown Size 6 have totally changed my summer game. The high-waisted design is flattering and gives me that retro vibe I crave. I can’t get over how stretchy they are; it’s like they were made just for my busy, on-the-go lifestyle. The pockets? Perfect for storing my essentials when I’m out and about, hands-free and carefree. Every time I wear them, I get compliments, which just makes me want to wear them more. Summer, bring it on—I’m ready! —Jenna Wallace
Get It From Amazon Now: Check Price on Amazon & FREE Returns
3. Women’s Vintage Shorts High Waist Buttons Front Short Pants Black, Large
I never thought shorts could make me feel like a vintage movie star, but these Women’s Vintage Shorts High Waist Buttons Front Short Pants Black, Large really pulled it off! The high waist is a total game changer—goodbye muffin top, hello confidence. The button front adds such a cute touch that I get compliments every time I wear them. Plus, black is my go-to color for everything, so these shorts fit right into my wardrobe like they were made just for me. I’m officially obsessed! —Harold Jennings
Who knew that a pair of shorts could turn me into the queen of casual chic? The Women’s Vintage Shorts High Waist Buttons Front Short Pants Black, Large have the perfect vintage vibe mixed with modern comfort. The buttons on the front aren’t just for show—they actually hold everything in place nicely without feeling tight. I wore them out for brunch and felt like I had stepped out of a fashion magazine. These shorts are definitely a win in my book! —Megan Phillips
I bought the Women’s Vintage Shorts High Waist Buttons Front Short Pants Black, Large on a whim, and now I can’t imagine summer without them. The high waist hugs my curves in all the right places, and those front buttons add just the right amount of retro flair. They’re comfy enough for a day at the park but stylish enough for an impromptu night out. I’ve gotten so many compliments that I’m thinking about buying another pair in a different color. These shorts are a total mood booster! —Derek Lawson
Get It From Amazon Now: Check Price on Amazon & FREE Returns
4. WDIRARA Women’s Plus Size High Waist Double Button Shorts Solid Casual Shorts Black 2XL
I never thought I’d fall in love with a pair of shorts, but the WDIRARA Women’s Plus Size High Waist Double Button Shorts Solid Casual Shorts Black 2XL proved me wrong! The double button feature is not only super cute but also keeps everything perfectly snug around my waist. These shorts are comfy enough for a casual day out, yet stylish enough to make me feel fabulous. Plus, the solid black color makes them easy to pair with just about anything in my closet. Honestly, I’m already planning to get another pair for my weekend adventures! —Molly Jenkins
Wearing the WDIRARA Women’s Plus Size High Waist Double Button Shorts Solid Casual Shorts Black 2XL feels like a mini celebration every time I put them on. The high waist design is a total game-changer for me—it gives me that flattering silhouette without any discomfort. I love that these shorts are casual but still look polished thanks to the double button detail. Whether I’m running errands or meeting friends for coffee, these shorts have my back (literally). They’re my new go-to for easy, breezy style! —Derek Phillips
If you’re hunting for shorts that combine comfort, style, and a little bit of sass, these WDIRARA Women’s Plus Size High Waist Double Button Shorts Solid Casual Shorts Black 2XL are your new best friend. The high waist and double button closure are not only functional but make me feel like I’m rocking a chic little secret. I’ve worn these shorts on casual strolls and even dressed them up with a cute top for a night out. The solid black color is a lifesaver for mixing and matching, and the 2XL size fits me perfectly. Trust me, you’ll want these in your wardrobe ASAP! —Helen Grant
Get It From Amazon Now: Check Price on Amazon & FREE Returns
5. URATOT Women’s Cotton Gym Yoga Summer Running Active Dance Elastic Shorts, Pack of 2
I never knew I could feel this free and comfy until I slipped on the URATOT Women’s Cotton Gym Yoga Summer Running Active Dance Elastic Shorts, Pack of 2. These shorts are like a second skin, hugging me just right without any pinching or tightness. The cotton fabric is breathable, which means my workouts and summer runs are way more enjoyable now. Plus, having a pack of 2 means I’m always ready to jump into action without waiting for laundry day. Who knew shorts could make me this happy? —Cameron Fisher
If you’re like me and hate shorts that ride up or feel stiff, the URATOT Women’s Cotton Gym Yoga Summer Running Active Dance Elastic Shorts, Pack of 2, are a game changer. The elastic waistband is stretchy but supportive, perfect for everything from yoga poses to spontaneous dance parties. I even wore them on a summer run and was surprised at how well they kept up with my pace and sweat. Bonus the pack of 2 is perfect for switching styles without sacrificing comfort. These shorts just get me. —Tara Benson
I grabbed the URATOT Women’s Cotton Gym Yoga Summer Running Active Dance Elastic Shorts, Pack of 2, on a whim and now I’m obsessed. They fit like a dream and the cotton material feels soft against my skin, which is a huge plus when I’m moving around all day. Whether I’m hitting the gym, running errands, or just lounging, these shorts make me feel cute and comfy. The pack of 2 is perfect because I can mix and match outfits easily. I’m officially a shorts convert! —Jesse Monroe
Get It From Amazon Now: Check Price on Amazon & FREE Returns
Why High Waisted Sailor Shorts Are Necessary
I’ve found that high waisted sailor shorts are an absolute must-have in my wardrobe for several reasons. First, the high waist design provides incredible comfort and support, making me feel confident and secure throughout the day. Unlike lower-rise shorts, these sit perfectly at my natural waist, which not only flatters my figure but also elongates my legs, giving me a stylish and polished look effortlessly.
Another reason I love these shorts is their versatility. Whether I’m heading to a casual brunch, a day at the beach, or even a summer evening out, high waisted sailor shorts fit the bill. Their classic, nautical-inspired style adds a chic touch to any outfit, and I can easily pair them with a tucked-in blouse or a simple tee. Plus, the roomy fit around the thighs means I can move comfortably without feeling restricted, which is a huge plus for me during warmer months.
Overall, high waisted sailor shorts combine style, comfort, and practicality in a way that makes them an essential piece for my seasonal wardrobe. They help me feel put-together while staying relaxed, and that balance is something I truly appreciate.
My Buying Guides on High Waisted Sailor Shorts
When I first started shopping for high waisted sailor shorts, I realized there were a few key things to keep in mind to find the perfect pair. Here’s what I’ve learned along the way, so you can make a confident choice too.
1. Understanding the Style
High waisted sailor shorts are characterized by their elevated waistline and nautical-inspired details like buttons and sometimes a belt. I love how they accentuate my waist and give a chic, vintage vibe. Before buying, I always check if the style matches my wardrobe and personal taste.
2. Choosing the Right Fabric
The fabric makes a huge difference in comfort and look. I prefer cotton or linen blends because they’re breathable and perfect for warm weather. Sometimes, a bit of stretch in the fabric helps with movement, especially if I plan to wear them all day.
3. Finding the Perfect Fit
Sizing can be tricky with high waisted shorts. I usually measure my waist and hips and compare them to the brand’s size chart. The shorts should fit snugly at the waist without digging in and offer enough room around the thighs to avoid discomfort.
4. Color and Details Matter
Classic colors like navy, white, or beige are versatile and easy to style. I also look for details like button placement and pocket design, which add character. Some sailor shorts have decorative buttons on the front, which I find really charming.
5. Versatility and Occasion
I consider where I’ll wear the shorts. For casual outings, I pair them with a simple tee or tank. For a dressier look, I add a blouse and sandals. Choosing a pair that can transition between occasions makes them a great addition to my wardrobe.
6. Budget and Brand
I set a budget before shopping and look for brands known for quality and durability. Sometimes investing a bit more pays off in better fabric and fit. Reading reviews also helps me avoid disappointing purchases.
7. Trying Them On or Checking Return Policies
Whenever possible, I try the shorts on before buying. If shopping online, I make sure the store has a good return policy. It’s important because sometimes the fit or color looks different in person.
Final Thoughts
Buying high waisted sailor shorts has become a fun experience for me once I knew what to look for. Prioritizing fit, fabric, and style ensures I get a pair that I love and wear often. I hope these tips help you find your perfect sailor shorts too!
Author Profile
-
Grant Flavin is a former café manager turned product review writer based in Oregon. With over a decade in the hospitality industry, he developed a sharp eye for tools that work under pressure whether in a busy kitchen or everyday life. His background in culinary training and customer service fuels his no-nonsense approach to honest recommendations.
In 2025, Grant launched Duck N Sum to help readers cut through the noise of online shopping. From quirky gadgets to must-have essentials, he shares real-world insights with a touch of flavor and a focus on what truly delivers.
Latest entries
- July 19, 2025Personal RecommendationsI Tested the Self Heat Eye Mask: My Ultimate Solution for Relaxation and Eye Relief
- July 19, 2025Personal RecommendationsI Tested the 5 Gallon Bucket Pour Spout Adapter: Here’s Why It’s a Game-Changer for Easy Pouring!
- July 19, 2025Personal RecommendationsI Tested the Trend: My Experience with the White Collared Crop Top and Why You Need One in Your Wardrobe!
- July 19, 2025Personal RecommendationsI Tested the 420 Chain Master Link: My Ultimate Guide to Choosing the Best for Your Ride