20 Ways to Wear High-Waisted Shorts

By on April 1, 2015

What is it about high-waisted shorts that makes every girl want to wear them? Is it the convenience of having something to wear that lets the air flow into your legs during the scorching hot days of summer? Perhaps it’s a way for the ladies to show off how meticulously they have been working on their legs all throughout winter. Maybe, it’s just another plain simple version of shorts that saves the girls the arduous task of finding far more fashionable and trendy pants to match with the tops.

Whatever the reason is, high-waisted shorts from the beautiful era of pinup are back and we are happy to welcome them into our wardrobes. Yes, they have been around for quite some time, and they are here to stay for another good number of years. Mostly worn in summer, high-waisted shorts are pretty high in the preference list of almost every young lady on days when the heat sucks the life out of you. With that being said, high-waisted shorts are much more versatile as a clothing item, and have more to offer than simply a way to cool you off in the blistering heat of the summer.

When high waisted shorts are combined with other chic pieces from the wardrobe, they can turn you into a mesmerizing diva. Experimenting with high-waisted shorts holds great rewards. Anything other than the plain simple summer tee is bound to look appealing once coupled with the high-waisted shorts. In addition to that, there are a host of accessories that can accentuate the appeal of high-waisted shorts. Not to mention, there’s a wide range of footwear that complements high-waisted shorts perfectly.

The possibilities are quite literally endless. You just need to stumble upon the right combination to make the best use of your high-waisted shorts. Fortunately, we are going to save you the trouble of asking around trendy strangers and browsing through fashion magazines. To know how to wear high-waisted shorts in the most fashionable way, simply check out these trendy 20 styles that we have prepared for you with great thought and care. Enjoy!

  1. Simple is not boring.
 Taylor Swift

Taylor Swift

Let’s start with something simple, shall we? If you aren’t feeling too fancy, then simply grab a plain tank top of any color, and pair it up with fabrics high waisted shorts. A pair of trendy loafers along with cute little dangling earrings makes for a pretty summer combination.

  1. Bohemian freedom.


The boho look has been in trend for some time now. Make use of it before it becomes outdated. All you’ll need is a loose sweater. To complement the oversized sweater, a pair of enormous heels is recommended. For the high waisted shorts, go denim, but choose a more interesting pattern.
3) At the beach. One of the best places to wear high waisted shorts is the beach. The colour of the shorts here is of the utmost importance. Make sure you pair up a of blue or white shorts with a delicate tank top of the same colour. This will make you stand out among the rest of the girls at the beach and make you look like a movie star.

  1. Summer vacation.


One of the best places to wear high waisted shorts is the beach. The colour of the shorts here is of the utmost importance. Make sure you pair up a of blue or white shorts with a delicate tank top of the same colour. This will make you stand out among the rest of the girls at the beach and make you look like a movie star.


  1. For a chilly evening.


High waisted shorts aren’t only applicable for summer time. They can be worn in colder days as well. A slouchy beanie, a scarf and over the knee socks are the perfect items of clothing to match dark high waisted shorts. A thin brown belt is preferable as well.

  1. Street casual.
Alexa Chung

Alexa Chung

You can’t forget that high waisted shorts are all about pulling off the casual look. A tucked in button-doww, with cute booties or flats can give you the casual rock star look when paired with classic denim high waisted shorts. Don’t forget to add the killer shades and the funky bracelets as well.

  1. All spring.
 Taylor Swift

Taylor Swift

Spring demands a drastic change in your attire. If you are trying to incorporate high waisted shorts in your spring collection, then put on well- fitting full sleeved sweaters and a pair of sandals. You may want to go for a scintillating wrist watch and a bag made of gleaming leather to grab a bit of the attention.

  1. With a bold crop top.
Miley Cyrus

Miley Cyrus

Crop tops and high waisted shorts are obviously a match made in heaven. However, if you truly want to look a class apart from the others, then try something different with your crop top. Why not add a casual shirt tied around your waist for a more distinct look, just like Miley Cyrus does here?

  1. Vintage look.


The tie-front shirt is not usually worn with high waisted shorts. Nevertheless, this a combination that you should definitely give a shot. Go for a flimsy shirt and a pair of vintage-looking dark shorts.

  1. Business-like.
Eva Longoria

Eva Longoria

So you think high waisted shorts are inappropriate for work? Well you think wrong. Go for beige (or any neutral color) shorts with an elegant blazer and a beautiful white button down shirt. Make sure the shirt’s tucked in and your pumps are of the matching color, and you’ll be ready to strut around like a corporate boss.

  1. Feminine and romantic.


From being the corporate hot shot lady to being the happy go round girl next door, the lacy shirt with white high waisted shorts offers the perfect feminine look you are aiming for. Don’t forget to belt your shorts and put on some plain silver rings to look more sweet and naive for the camera.

  1. Urban chic.
Kendall Jenner

Kendall Jenner

Crop tops can be a bit too revealing at times. Go for the skinny crop tops and pair them up with floral high waisted shorts for the ultimate urban chic look. For accessories, you can put on a hat and a thick strapped watch. Footwear should be kept simple with the usual heels.

  1. With a cardigan.
Olivia Palermo

Olivia Palermo

Another classic look that you can try out is a light cardigan with glaring dark high waisted shorts. Don’t forget to add an oversized bag to complete the look.

  1. Cowgirl look.


Tied up shirt will make your whole look appear frivolous and playful. A perfect look for all the cowgirls out there. Don’t forget to put on your combat boots with this attire. This is the perfect way to look effortlessly cool without being too mundane.

  1. Classy.
Kate Moss

Kate Moss

High waisted shorts aren’t just for the simple casual outfits. You can put on a polished and uptown look with these shorts as well. Pair them up with a trendy spring jacket. Keep the jacket buttoned up for a more polished look, or loose for a business-casual one. You may event want to tie your head in a bun.

  1. With tights.


For those who are not comfortable with showing off their legs, you can always resort to wearing tights under those high waisted shorts. A boat neck top, with black and white stripes, would be the perfect way to complement to the shorts. Don’t go heavy on the jewellery with this attire.

  1. Pin-up girl.
 Scarlett Johansson

Scarlett Johansson

Choose a well-fitting shirt or a cardigan and tuck it in. Don’t forget to go for a fancy pair of denim shorts and add a belt to create more curves. To further amplify your appeal, put on a dazzling golden watch and a pair of B shades.

  1. Oriental.


Enough with oriental cuisine, time for some oriental fashion. Throw on a long, light kimono on top of a crop top. Dark blue denim high waisted shorts will look fantastic with this top combination. Keep the heels aside for this attire, and go for some traditional flats.

  1. Bright and colorful.


High waisted shorts don’t always have to be bleak and dark in colour. Wear the floral ones or the ones with bright prints that are becoming increasingly popular. It gives you the perfect fresh summer feel. Add a crochet or lacy top and your “Alice in Wonderland” look is ready to go.

  1. Two basics.


No need to overthink this classic look, as a simple white shirt will go perfectly well with a pair of denim high-waisted shorts. You might want to add some accessories, but a bright lipstick should generally be enough for this chic and simple look.

  1. With a spring coat.


Wear a spring coat on top of your favourite high-waisted shorts for a new sexy look. Make sure the bottom buttons open your shorts to the public. The look is indeed very outstanding and attractive and will make sure all eyes are on you.

With so many combinations to pick from, you may become a little flustered about wearing high waisted shorts. Take a breath and spend some time checking your closet for the appropriate tops. Coming up with the perfect outfit with high waisted shorts requires a good deal of thinking and creativity.

(all images are sourced via pinterest)


  1. Evie

    April 30, 2015 at 9:15 pm

    #11 is actually Kylie Jenner, not Kendall

    • web admin

      web admin

      May 1, 2015 at 2:22 pm

      Excellent eye–thank you for pointing that out to us. If you have time, there are other articles on HerInterest that may intrigue you. Take a moment and look around!

Leave a Reply

Your email address will not be published. Required fields are marked *