How to Wear High Waisted Shorts

Photo Credits: 1 & 2: Pacific Coast News, 3: ELLE
Thanks in part to retro-styled shows like Mad Men, vintage cut lingerie, swimsuits, dresses, and more have slowly been making their way into mainstream fashion. First it was high waisted skirts, then pants, and now it’s hard to walk into a store without seeing a wide array of high waisted shorts.
I’m guessing that you probably feel the same way about them as I did when I first noticed them — sure they look great on waifs like Nicole Richie, but are they actually wearable for the average girl? The answer is yes — it just takes a little bit of creative styling! I’ve scoured the web for the absolute best tips on how to make high waisted shorts work for you, and compiled them all here for your sartorial pleasure :)
Not sure what to wear with high waisted shorts? Read on to learn all the tips!
Tips and Tricks for Wearing High Waist Shorts
- “High Waisted” is relative. To rock this trend, you don’t need to go out and find a pair of shorts that reaches above your belly button. If you have a shorter torso (or a larger bust), go for styles that are cut comfortably over your hip bones, but not all the way up to the smallest part of your waist. Because low-cut styles have been popular for so long, even a mid-rise cut will give you the look of the trend!
- Tuck in your shirt. This is a no-brainer, but show off your trendsetting ways but tucking in your top and emphasizing your new shorts.
- DIY a pair! A good way to test the waters on this trend is to pick up a pair of jeans from a thrift shop and cut them into shorts yourself. Cuff the hems for an extra cute look. Don’t worry if you grab a pair that’s a little big on you — the style will look great with a belt, and the looseness throughout the butt and thighs will look more “street chic” than “Mom Jean!”
- Show some leg. To balance out the length of high waisted shorts, I love the look of Nicole Richie’s (pictured above) short-shorts! This will elongated your legs and keep you from looking stumpy, if you’re worried about that sort of thing.
- Embrace the more mature look. Another way to wear the high waisted shorts trend is to go for a dressier look, like Blake Lively and our street style fashionista did, above. Pair your shorts with heels to feel extra elegant.
- Consider the top. A tank or simple t-shirt will look chic with high waisted shorts, but pair them with a button-down dress shirt for a Katherine Hepburn aesthetic.
- Wear them with a cropped top! If you’re a little tummy-shy like me, high waisted shorts are perfect for pairing with cropped tops! The only skin people will see is the part between your belly button and ribcage — the tiniest place on most girls’ torsos.
- Try them with swimsuits. High waisted shorts, especially the nautical variety, will look fabulous paired with your favorite bikini for a fun new cover-up. These will look great and make you feel like you’re straight out of a movie filmed at the French Riviera!
- Be confident! It takes a bold girl to rock these babies — hold your head up high and let the world know how great you know you look!
Outfit Inspiration

Hat, Belt, Shorts, Tank, Shoes, Purse, Earrings
This look is simple, chic, and perfect for spring or summer! Mid-rise shorts like these will give you the look and feel of high waisted shorts, but won’t cut off your torso too much. Tuck in a striped tank top, and accessorize with a belt, fedora, feather earrings and wedge sandals.

Shorts, Top, Cardigan, Shoes, Lipstick, Necklace
This look is flirty, girly, and oh-so retro fabulous! Have you picked up one of those foxy bralette tops, but are still wondering how to wear it? Pair it with high waist shorts for coverage and a taste of pin-up girl style! Tone down the look with a cardigan, but stay looking chic with some foxy wedges. Finish your outfit with an eye-catching necklace and some glamorous red lips!

Shorts, Belt, Headband, Tee, Sunnies, Shoes, Bracelets
This outfit is casual like the first look, but a little more on the hippie/boho chic side. High waisted hot pants will look balanced paired with a relaxed black v-neck. Style your outfit with a hippie headband, gladiator sandals, a stack of bangles, and printed wayfarers.

Shorts, Ring, Blouse, Shoes, Clutch
This look is romantic and a bit dressy, perfect for a date or another snappy-casual type situation. This green blouse will look stunning paired with structured, peach-colored shorts. Add a fancy cocktail ring and your go-to pair of simple heels. A soft look like this would look great with those loose, soft curls I’ve been seeing all over Pinterest! Finish with a clutch — I’ve been obsessing over the box clutches from House of Harlow, but there are plenty of cheaper look-alikes out there!
Thoughts?
Would you wear high waist shorts? How would you wear them? What do you think about other vintage-inspired fashions? Are there any other trends you’re having trouble figuring out how to style? Leave a comment and tell us what you think!!
Posted on on March 15, 2012 / Filed Under: Fashion Tips / Tags: High-Waisted Shorts, Shorts, Spring, Spring 2012, Trends















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Laura
I love the high-waisted trend – so chic! Love my high-waist trousers/jeans/pencil skirts – need to get in on the shorts action!
Leira Zetroc
High waisted shorts definitely give a casual outfit a dressy and retro element to it.
PrefectHermione
I’d wear the third and fourth looks. I’m glad higher waists are coming back, I generally don’t like low rise.
Stephanie
I love the outfit ideas! So cute! I have a pair of white high waisted shorts that I paired up with a short bright pink shirt and turquoise blazer. Such a fun and colorful summer outfit!
lorraine
I love this trend but, unfortunately here in mexico city if you wear shorts every single man look at you like if you were fast food (ready to go and eat you!) so i feel really sad cause im not going to wear some high waist shorts. But i definately love this high waist shorts
Alice
I love the How to series. Please do an article on “How to Wear Over-the-Knee Socks”!
Vanessa
I love myhighwasited shorts. It definitely feminize my look if I wear a fitting blouse and they always look girly and in style. Pair them with some wedges and I’m hot to trot!
Jessica - UCLA
Hey Alice, I noticed your comment & wanted to share with you an article we did back in Fall about how to wear over the knee socks. It’s specified in the title to be fall looks, however I think it’s still applicable to spring! Hope this is helpful :] http://www.collegefashion.net/fashion-tips/ask-cf-how-do-i-wear-thigh-high-socks-for-fall/
Chloe
Very nice post! Loved the part about high waisted being relevant! Your butt cheeks should not hangout of the bottom of your shorts! It says show some LEGS not butt! haha! Great outfits as well!
Disha
LOVE high waisted shorts. Especially try to get ones that really stand out with buttons in the front or a bow. Make it look a little different :)
Rose
Love!!!!! The second and fourth looks are FABulous! omg!!!
Iris
I love love love high waisted shorts! They are probably my favorite trend to come along ever ever! It makes me normally short body look long and my legs look thinner! I never really thought about the confident part of wearing these shorts though, I just throw them on and think I look great (too confident? lol). I think this one of those trends that ANYONE can wear and rock it. Doesn’t matter your shape I think high waisted shorts just make your waist look thinner and your legs look longer.. and who doesn’t love that?
Love love love this post (I did a similar one on my blog as well) Thanks for it <3
C
4th outfits my favorite but the 2nd is really cute also! :) I love the high waisted short look! Great post
Rachel
Really loving that clutch!
Jenny
I adore my high waisted shorts and wear them most of the time – more often with tights then not. They show off my legs nicely but still hide my not-stick-thin stomach :D x
Anna
Love this trend although I don’t think I have the legs for it!
audrey
i loooove high waisted shorts! my favorite pair used to be my mother’s back when she was young and i love them !
Kathy
I’ve recently become obsessed with high-waisted shorts, and there are a couple pairs from Modcloth that I’m just drooling over. This one pair in particular is mustard yellow, so I’m in a horrible dilemma over getting them. Not only because of the price, but because I tend to avoid yellow, orange, and brown as they tend to make me look jaundiced.
Elyse
Just bought my first pair of high-waisted denim shorts this week! I have high-waist trousers too and I lovelovelove the trend, so the denim works for more casual spring/summer outfits! It’s so close to being warm enough to wear them!
Elle
Love High waisted shorts!
Still confuses me with the difference between British and American fashion….. I was late on the high waisted bandwagon in Britain and I got my first pair last two summers ago lol!
xxxx
Alyssa Nicole
All these ensembles arre so inspiring..
Pame
Love Blake’s look!!! Love this trend!
Irev
The first look is perfect summer. It’s going to be perfect since it is already summer here. The third look is another one that I love. I like the boho feel of the outfit. :)
Shay Monet
I love highwaisted stuff! It perfectly balances my hour glass figure
Joelle
High waisted is sooo good for girls with hips! It emphasizes a tiny waist and makes you look so feminine and curvy! I got an awesome pair of vintage cornflower blue high waisted Dockers last fall and I can’t wait to pull them out for spring! Love this :)
PB
LOVE high-wasted shorts!
Side note: Could you do a post about how to wear high-low skirts? Thanks!
Ashley
Such good ideas! I sell high waisted shorts on my Etsy store and this gives me great ideas of what I could style them with!
Dee
Love high waisted shorts! Great outfit ideas, but what do you suggest for rocking high waist shorts for a night on the town? I want to look sexy but NOT hoochie. lol
helery
Thank you so much! This is exactly what I was looking for. I have a pair of dressy black and white striped high waisted shorts with gold buttons… any suggestion s on the top and shoes? Thank u so much
regan
i would love to wear high waisted shorts but can never find nun.thats cheap,ndd i dnt have anything to wear with them,plus i cant wear heels,im too young says my mom