How to Wear High Waisted Shorts: 5 Ideas For a Perfect Summer Look

It's official! High waistlines are back in style, and the new season's shorts are a great way to rock the look! If you still don't know how to wear high waisted shorts, read the best tips for rocking this summer staple.

When high waistlines first started reappearing in stores a few seasons ago, like a majority of people, I just sort of laughed them off as a fleeting fancy that the fashion industry was trying out on us. I, like so many others, never thought for a minute that high waistlines would come back into style again.

Fast-forward a couple of fashion seasons, and it appears that the industry's love affair with the higher waistline was not just a passing fancy after all, and high waistlines are here to stay. At least for now.

High Waisted Shorts Are Amazing!

how to wear high waisted shorts

There's no other way to say it – as it turns out, we've been missing out on something huge by not taking advantage of the high waisted shorts!

Because when you think about it, we should be rejoicing: high waistlines are infinitely more comfortable than their low-slung predecessors and are the perfect pairing if you want to achieve that seventies look that's all the rage right now.

Also, they cover your midsection hiding any unwanted bulges, cinch the midriff into a feminine shape (without a corset, thanks very much), and provide shape and a hint of vintage glam to bodies lacking curves (like mine). Long story short, high-waisted shorts are The Business.

However, I am one of those who were alive and well and in our element in the über-low waistband nineties; we fear it is just a little too easy to accidentally wander into “mom jeans” territory when you choose a high waistband.

Shorts, in particular, pose a special conundrum: on one hand, a higher waistband on a pair of shorts helps to keep them from rising up and makes your legs look a mile long. On the other, high waisted shorts are actually a little trickier to style than their full pant legged counterpart, and can easily look dated if you miss a step with your styling. That's where these little pieces of sartorial research science come in.

I'm hoping that my efforts in scouting every corner of the internet, my personal archives, and a whole lot of fashion magazines have armed this quick-fix style guide with enough tips to figure out how to wear high waisted shorts in all the upcoming seasons and no matter your body type!

1. Pay Attention to Style & Fit

how to wear high waisted shorts

Not all high-waisted shorts are created equal; there are a lot of variations within the genre, so it's important to do a little research and find out what styles look best on your particular body type.

“High waisted” is a rather general term, so you will have to try out more styles and brands to know where you stand. While one company's version of the look night mean you feel the garment is practically up to your neck, another's might be a much more moderate cut, and work for your body. Sadly, this is one item where trying it on is going to be essential – sad news for those of us who love to internet shop.

While some types of clothing look great when they're oversized, high-waisted shorts do not fall into this category. To look modern and intentional, they have to fit impeccably. Too big, and you will look like you're drowning. Too small, and you are in danger of showing all sorts of unfortunate anatomical features that you secretly hate.

If you are petite, a pair of high-waisted shorts that gently graze the tops of the thighs can add inches to your height. However, it's best to avoid shorts that have too much volume in their design, as this can easily overwhelm a small frame.

Those who are a bit curvier (especially in the thighs) should choose a pair of shorts that have a bit of flare to them, and are made of soft fabric that drapes well. The high waist emphasizes the smallest part of your body, balancing the silhouette, and your legs will look miles long.

Tall and slender women can get away with just about any shorts style, and look great in structured, fitted high-waisted shorts with a retro flair. However, if you have a long waist, be wary of waistlines that are extremely high, or you will risk making your upper body appear stumpy. However, this can sometimes be balanced out by wearing a higher neckline with your high waisted shorts.

2. Keep it Casual

how to wear high waisted shorts


While shorts in this day and age are no longer the sole symbol of dressed-down weekends and beach days, in the summer season (or any time you are inspired to wear a pair of shorts that does not require a blazer or a pair of opaque tights), high-waisted shorts are at their most versatile as a casual look.

Despite the fact that high-waisted shorts actually provide more overall coverage than their low-slung predecessors, the fit around the waist can be quite body-conscious, so it is best to balance the look with a soft, flowing, voluminous top.

Choose a lightweight, oversized t-shirt or sweater, and tuck the front of the top into the waistband; this gives the look a bit of effortless drape while still providing a bit of waistline definition.

If you are the type who prefers to mix it up a bit more, instead of pairing your high-waisted shorts with a sweater or tee, try pairing it with that ultimate wardrobe staple – an oversized button-down shirt.

For best effect, make sure that you choose a shirt that is made of a soft (if not downright luxurious) material and has a lovely drape to it. Wear it tucked into your shorts, but blouse it a bit and roll-up the sleeves; this gives you an classic yet effortless appeal.

3. Show Some Skin

how to wear high waisted shorts

If you're the more adventurous type, you can opt for a cropped top – just make sure you choose one that has a bit of volume and looks modern; a body-conscious cropped top paired with high-waisted shorts may make you look like you are heading to an 80s revival party.

If you have a smaller bust, choose a top that has a boxy cut, perhaps even with a high-low hemline (higher in the front, lower in the back). The high waistband of the shorts paired with the flowing volume of the cropped top will leave just enough skin showing to look intriguing, while still leaving enough to the imagination to be chic.

Larger-busted women may prefer to rock a more retro look by pairing a fitted (not tight) button-down shirt with their high-waisted shorts, tying a knot at the waistline to show just the smallest bit of midriff.

If you really must wear a body-conscious top with your high-waisted shorts, try pairing a more structured bustier style top with your shorts, and adding a lightweight kimono or cardigan layered over the top. This look is essentially taking advantage of both of the aforementioned looks; you're working the bare midriff, yet still using a lot of flowing fabric volume to keep the look balanced.

4. Master Your Shoe Game

how to wear high waisted shorts


Picking the right shoes to wear with your high-waisted shorts look is critical.

If you are going to a summer music festival or the beach and are looking to wear a flat shoe, opt for a simple pair of flat, strappy sandals in a neutral or burnished metallic shade.

The simplicity of a flat sandal keeps everything on the light side, and won't compete for attention with the flow of your top, visually cut off the legs at an unflattering angle, or make you look like you try too hard, like overly-complicated shoes would.

If you want something a little sportier, try a pair of canvas sneakers with your shorts. While this is definitely the most dressed-down shoe you can pair with your look, often it may provide a great contrast with a floaty, feminine blouse, and inject your look with a bit of youth and edge.

For those who simply don't feel like themselves unless they are in a pair of heels, there are plenty of great options as well.

One of the best things about a pair of high-waisted shorts is that it makes your legs look really, really long. Take advantage of this with a pair of nude-colored (whatever “nude” is for you) wedge heels. The seventies vibe of the high-waisted short and flowing blouse is perfectly balanced by a heavier shoe like a wedge and it gives the look a cool-girl, bohemian vibe.

If you need more inspiration, check out our guide to the different shoes you can wear with shorts.

5. Boots and shorts

how to wear high waisted shorts

If you're feeling like rocking a slightly edgier look, try pairing your high waisted shorts with a pair of ankle booties, combat boots, or if you're really looking to amp up the drama, a pair of over the knee boots.

Ankle boots are delightfully bohemian and feminine, and look great either in a natural shade worn with bare legs, or in black with a pair of opaque (or contrasting) hosiery.

Try pairing them with a flowing peasant blouse or kimono, and you have the perfect mix of feminine and edge. If you're feeling a little bit rock and roll, channel your inner 90s child and try pairing a pair of high-waisted denim cut-off shorts with a flannel shirt and a pair of combat boots.

For colder climates, pair your shorts with a chunky sweater and some over the knee boots. One word of caution, however: if you're opting for tall boots with your high waisted shorts, choose a pair that is either flat or has a slight wedge. A stiletto-heeled boot with a pair of shorts is probably a bit too “Pretty Woman” for the real world, and while “hooker with the heart of gold” is a great theme for a movie, it's something you definitely want to avoid in your sartorial life.

While you may still be a bit unsure of this new crop of high-waisted shorts, these simple style tips can help you ease them seamlessly into your wardrobe.

Trust me when I tell you that after you choose your first pair and discover how comfortable and universally flattering they can be, you'll never want to go back to the days of the low-rise. That is, until they come out with something new next season, am I right?

About the author

Kristin Buchholz-MacKillop

Kristin is an American writer based in the Scottish Highlands. She is a saxophonist, an obsessive tennis player, a U.S. Air Force Veteran, and holds a Master's degree as an Acute Care Nurse Practitioner. She is the author of the online style blog

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