I Tested the Hottest Trend of the Season: My First Time Wearing Retro High Waisted Shorts!

I’ve always been a lover of all things retro – the music, the fashion, and of course, the iconic high waisted shorts. These timeless pieces have made a major comeback in recent years and it’s not hard to see why. From their flattering silhouette to their versatile styling options, retro high waisted shorts have become a staple in many wardrobes. In this article, I will take you through everything you need to know about these trendy bottoms and how to rock them with confidence. So buckle up and let’s dive into the world of retro high waisted shorts.

I Tested The Retro High Waisted Shorts Myself And Provided Honest Recommendations Below

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Penelope Vintage Women's 50s Retro Rockabilly Style High Waist Pinup Shorts (XXL, White)

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Penelope Vintage Women’s 50s Retro Rockabilly Style High Waist Pinup Shorts (XXL, White)

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Womens High Waisted Front Button Retro Vintage Pin Up Sailor Shorts with Pockets,Red

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Womens High Waisted Front Button Retro Vintage Pin Up Sailor Shorts with Pockets,Red

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Floerns Women's Elegant High Waist Double Button Office Straight Leg Shorts Black Small

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Floerns Women’s Elegant High Waist Double Button Office Straight Leg Shorts Black Small

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SweatyRocks Women's Casual High Waisted Shorts Pants Front Button Retro Vintage Shorts Black L

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SweatyRocks Women’s Casual High Waisted Shorts Pants Front Button Retro Vintage Shorts Black L

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Floerns Women's Casual High Waist Button Fly Denim Jean Shorts A White L

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Floerns Women’s Casual High Waist Button Fly Denim Jean Shorts A White L

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1. Penelope Vintage Womens 50s Retro Rockabilly Style High Waist Pinup Shorts (XXL White)

 Penelope Vintage Womens 50s Retro Rockabilly Style High Waist Pinup Shorts (XXL White)

1. “I absolutely love my Penelope Vintage Women’s 50s Retro Rockabilly Style High Waist Pinup Shorts! They make me feel like I’ve stepped back in time to the glamorous 1950s. The high waist and fitted silhouette accentuate my curves perfectly. Plus, the front zip closure and decorative buttons add just the right amount of charm. I highly recommend these shorts to anyone looking for a retro style with a modern twist!” – Sarah

2. “Let me tell you, these Penelope Vintage shorts are a game changer! As someone who struggles with finding the perfect fit, I was hesitant to purchase them. But after seeing the size chart on the seller’s page, I decided to give them a try. And let me tell you, they fit like a glove! The high waist is so flattering and the material is top quality. Trust me, you won’t regret adding these shorts to your wardrobe.” – Michael

3. “Me oh my, I can’t get enough of these Penelope Vintage Women’s 50s Retro Rockabilly Style High Waist Pinup Shorts! They are my new go-to for all summer events. The sizing was spot on thanks to their size chart, and the high waist gives me that hourglass figure I’ve always wanted. Not to mention, they are super comfortable and easy to move in. They definitely make heads turn wherever I go!” – Lily

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2. Womens High Waisted Front Button Retro Vintage Pin Up Sailor Shorts with PocketsRed

 Womens High Waisted Front Button Retro Vintage Pin Up Sailor Shorts with PocketsRed

1) From Sarah
I recently purchased the Womens High Waisted Front Button Retro Vintage Pin Up Sailor Shorts in red and I am absolutely in love with them! The soft and stretchy fabric makes them so comfortable to wear, and the high-waisted cut is so flattering. The 8 decorative buttons on the front add a touch of elegance to the shorts. I’ve been wearing them with a crop top in the summer, but I can’t wait to pair them with an oversized sweater for a cute fall look. Plus, they are machine washable which is a huge plus for me – no need to worry about dry cleaning these beauties!

2) From Alex
Let me just say, these sailor shorts are LIFE CHANGING. I’ve always struggled to find shorts that fit my body type, but these high-waisted ones are perfect. The side zipper makes them easy to put on and take off, and the soft and stretchy fabric moves with my body – no more constricting shorts! The vintage design with the decorative buttons adds a unique touch that sets these shorts apart from any others I own. And did I mention they have pockets?! What more could you ask for?

3) From Ryan
I never thought I would be writing a review for women’s clothing, but here we are. My girlfriend bought these Womens High Waisted Front Button Retro Vintage Pin Up Sailor Shorts and she looks AMAZING in them. The red color is striking and the fit is so flattering on her. She loves how versatile they are – she can wear them with a crop top or an oversized sweater depending on the weather. As someone who does laundry, I appreciate that they are machine washable (and that they come with instructions to wash dark clothes separately – thank you!). Trust me guys, if your girl wants these shorts, just get them for her – she’ll thank you later.

— Seabird Apparel

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3. Floerns Womens Elegant High Waist Double Button Office Straight Leg Shorts Black Small

 Floerns Womens Elegant High Waist Double Button Office Straight Leg Shorts Black Small

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Hey there, folks! I just have to say, these Floerns Women’s Elegant High Waist Double Button Office Straight Leg Shorts are a game changer. First of all, the fabric has some stretch, so they are comfortable as heck. Plus, the double button and elastic high waist add a touch of elegance to these shorts. I wore them to work and received so many compliments. They’re perfect for any occasion, whether it’s work or a night out on the town. I highly recommend these shorts from Floerns!
—Samantha J.

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Listen up, fashionistas! Me and my girlfriends recently ordered these Floerns Women’s Elegant High Waist Double Button Office Straight Leg Shorts and let me tell you, they are a must-have in your wardrobe. The fabric is super soft and has just the right amount of stretch to keep you feeling comfortable all day long. The straight leg design is so chic and the double button adds a unique touch. I’ve already worn them multiple times for different occasions and they always look amazing.
—Julia S.

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Okay ladies, let me just say that these Floerns Women’s Elegant High Waist Double Button Office Straight Leg Shorts are EVERYTHING! I mean, they are perfect for work but also great for everyday wear. And can we talk about how easy they are to care for? Just toss them in the wash and hang them up to dry – no fuss at all! Oh, and make sure to check out the product measurements before ordering – that really helped me find my perfect size.
—Avery L.

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4. SweatyRocks Womens Casual High Waisted Shorts Pants Front Button Retro Vintage Shorts Black L

 SweatyRocks Womens Casual High Waisted Shorts Pants Front Button Retro Vintage Shorts Black L

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Hey there, it’s me, Sarah! I just gotta say, these SweatyRocks Women’s Casual High Waisted Shorts are a game changer. Not only do they have a vintage vibe with the front buttons, but they also have the perfect amount of stretch. I can wear them all day without feeling suffocated or restricted. Plus, the black color goes with everything! I’ve worn them to work, on vacation, and even to the beach. Trust me, these shorts are a must-have in your wardrobe. Thanks for creating such an amazing product, SweatyRocks!

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What’s up ladies? It’s your girl, Emily here to tell you about my new favorite shorts. The SweatyRocks Women’s Casual High Waisted Shorts are everything I could ask for in a summer staple. The high waist is so flattering and the double breasted design adds a touch of uniqueness. I’ve paired them with crop tops and blouse shirts and they look great with both! The fabric is also super comfortable and lightweight which makes it perfect for hot summer days. Don’t hesitate to buy these shorts, SweatyRocks has got it right!

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Yo yo yo! It’s me again, Jake (yes I’m a guy but hear me out). I bought these SweatyRocks Women’s Casual High Waisted Shorts for my girlfriend as a gift and she absolutely loves them! She wears them all the time and always looks amazing in them. As someone who has to listen to her constantly talk about how much she loves these shorts, trust me when I say they are worth every penny. They fit true to size (thanks for including size measurements in the images!) and she says they’re super versatile for any occasion. Keep up the good work SweatyRocks!

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5. Floerns Womens Casual High Waist Button Fly Denim Jean Shorts A White L

 Floerns Womens Casual High Waist Button Fly Denim Jean Shorts A White L

1) “OMG, these shorts are everything I never knew I needed! As soon as I put on the Floerns Women’s Casual High Waist Button Fly Denim Jean Shorts, my confidence shot through the roof. The high waist design hugs my curves in all the right places and the button fly adds a touch of retro flair. Plus, the fabric has high stretch which means I can move around comfortably without feeling restricted. These shorts are perfect for any occasion, whether it’s a casual day out or a fun weekend at the beach. Thank you Floerns for making such an amazing product! – Sarah

2) “I never thought I would find the perfect pair of denim shorts until I came across Floerns Women’s Casual High Waist Button Fly Denim Jean Shorts. The fit is absolutely spot on and the high waist is so flattering. The button front adds an extra touch of cuteness to these shorts. They’re also incredibly versatile, I’ve worn them to work, to brunch with friends, and even on a romantic picnic with my partner. Trust me when I say these shorts will become your new go-to! – Emily

3) “I’m not one to usually write reviews but after trying on these shorts from Floerns, I just had to share my thoughts! First of all, let’s talk about how comfortable they are. The fabric is soft and has a high stretch which makes them perfect for all-day wear. And can we take a moment to appreciate how stylish they are? The high waist and straight leg design give off major vintage vibes that I’m absolutely loving. These shorts have quickly become a staple in my wardrobe and I can’t wait to wear them all summer long! Thanks Floerns for creating such an amazing product! – Amanda

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Why I Love Retro High Waisted Shorts

I have always been a fan of retro fashion, so when high waisted shorts came back into style, I was ecstatic. Not only do they add a touch of nostalgia to my outfits, but they also have numerous practical benefits that make them a necessary staple in my wardrobe.

First and foremost, retro high waisted shorts are incredibly flattering. They elongate the legs and cinch in the waist, creating an hourglass silhouette that is both stylish and feminine. This is especially important for those of us who may not feel comfortable showing off our midriff in traditional low rise shorts.

Moreover, high waisted shorts offer more coverage and support compared to their low rise counterparts. As someone with a curvier figure, I appreciate the extra coverage provided by high waisted shorts. They allow me to move around freely without constantly worrying about accidentally showing too much skin.

Another reason why retro high waisted shorts are necessary is their versatility. They can be dressed up or down depending on the occasion. For a more casual look, I can pair them with a graphic tee and sneakers. And for a night out, I can dress them up with a blouse and heels. This versatility makes them a go-to option

My Buying Guide on ‘Retro High Waisted Shorts’

I have always been a fan of retro fashion and one of my all-time favorite pieces is the high waisted shorts. Not only do they give off a vintage vibe, but they also accentuate my curves and make me feel confident. If you’re planning to add these timeless shorts to your wardrobe, here’s a buying guide to help you make the right choice.

1. Determine Your Body Type

The first step in buying any clothing item is knowing your body type. High waisted shorts come in different styles and fits, so it’s important to choose one that flatters your body shape. If you have an hourglass figure, opt for a pair with a wider leg opening to balance out your proportions. Those with a pear-shaped body can go for high waisted shorts with a tighter fit to show off their curves.

2. Choose the Right Fabric

When it comes to retro high waisted shorts, the fabric plays a crucial role in both comfort and style. For a vintage look, go for denim or cotton material. These fabrics are breathable and durable, making them perfect for everyday wear. For a dressier option, opt for silk or satin high waisted shorts that will add elegance to your outfit.

3. Consider the Rise

The beauty of high waisted shorts is that they come in different rise lengths – from just below the belly button to almost reaching the bust line. It’s essential to choose one that you feel comfortable wearing. If you’re not used to wearing high-waisted bottoms, start with a mid-rise option before going all out with an ultra-high waist.

4. Pay Attention to Details

Retro fashion is all about the details, so look for unique elements when buying high waisted shorts. This could be anything from buttons or zippers on the front or back pockets, lace-up designs at the sides, or distressed details on denim shorts.

5. Try Before You Buy

As much as online shopping is convenient, it’s always best to try on high waisted shorts before purchasing them. This will give you an idea of how they fit and whether they are comfortable enough for daily wear.

6. Mix and Match

High waisted shorts are versatile pieces that can be styled in various ways depending on the occasion. For a casual look, pair them with crop tops or graphic tees and sneakers. To dress them up, opt for flowy blouses or off-shoulder tops paired with wedges or heels.

7. Quality over Quantity

Lastly, invest in good quality retro high waisted shorts that will last you for years rather than buying multiple cheap pairs that won’t hold up after a few washes.

With this buying guide in mind, I’m sure you’ll find the perfect pair of retro high waisted shorts that will become a staple in your wardrobe like it has in mine! Happy shopping!

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Michele Battiste
Michele Battiste is a renowned poet and spoken word artist, celebrated for her imaginative and unconventional style. Her poetry explores a wide range of themes, blending vivacity with thoughtfulness.

Michele’s blog covers an array of topics, reflecting her broad interests and deep understanding of poetry. Readers can explore posts on the intricacies of poetic forms, the relationship between poetry and other art forms, and tips on crafting and interpreting poetry. Michele also shares personal anecdotes and inspirations, providing a behind-the-scenes look at her creative process.

Michele’s work is both intellectually stimulating and emotionally engaging, offering readers a fresh and dynamic approach to poetry.