High-Waisted Shorts That Are Booty-Approved

Shop WeWoreWhat High-Waisted Shorts, High-Waisted Denim Shorts Outfit, Tilden of To Be Bright

I’ll be frank here & I haven’t mentioned it as much as I probably should have…but my derrière scales on the larger side when it comes to my body frame. Don’t get me wrong, I have no issues with it and absolutely love the way I look (which can be hard to admit to myself every day, but nonetheless I do love the body I’m in.) However, it does make finding the right fitting pair of high-waisted shorts a bit difficult.

Think about it – a high-waist short fit has to be ultra precise. The waistband has to be small enough to fit comfortably on the more narrow part of your lower half (waist) while still being able to slip over the largest part (booty) AND providing max coverage for those backend cheeks at the same time.. It literally sounds impossible to achieve – and as a result, that’t why there’s only a handful of brands/styles that have achieved the impossible.

Because I love the high-waisted look, I made it my mission to find a pair of shorts I could proudly wear this summer. Denim is the hardest fabric to find success with but I happened to discover two pairs that absolutely impressed me. In fact, I’m wearing one of the pairs as we speak because it’s genuinely that comfortable wearing while sitting at my computer.

Shop WeWoreWhat High-Waisted Shorts, High-Waisted Denim Shorts Outfit, Tilden of To Be BrightShop WeWoreWhat High-Waisted Shorts, High-Waisted Denim Shorts Outfit, Tilden of To Be BrightShop WeWoreWhat High-Waisted Shorts, High-Waisted Denim Shorts Outfit, Tilden of To Be Bright

The first pair I want to highlight is this denim shorts pair above. These are by Shop WeWoreWhat designed by Danielle Bernstein. Say what you want about caving to another blogger’s design but the girl seriously understands the high-waist game. I probably wear these every other day, sporting the white high-waisted pair also made by Danielle on the other days.

While I’ll admit they do run a teeny bit up my bum when I kneel down, I still find them to be the closest pair to perfect in terms of the wash & the waist height. For that, I can handle a bit of the cheek flashing moments. I will say that the white denim pair doesn’t ride up as much on me, if that says something. Maybe like jeans, no matter the brand, denim shorts are always a gamble in the size & fit. Considering I bought and tried these shorts sight unseen (aka online), I’ll say this is a big win.

Although these shorts are no longer in stock on the Shop WWW website, there are plenty of other retailers (big & boutique) that carry her collections. I know for a fact the adorbs store Brooke + Bel in Hoboken carries the white denim pair (as of now) so you just have to do some digging once you determine the places selling her clothing. You can also take a look at some of the styles below which are very similar to this pair & might be worth trying out (& in case they don’t work, free returns for the win!)


Shop WeWoreWhat Etoile Shorts, High-Waisted Shorts Outfit, Tilden of To Be Bright

This next pair of high-waisted shorts also happens to be Shop WWW (what can I say, the fit is always done right!) These are the cotton-lined Etoile Shorts, which the style happens to be in-stock & on sale at the moment. I sized up like I normally do for non-denim shorts (i.e. Medium) and I actually wish I got the small, hence the makeshift belt action up top. However, I do like the fit of the medium a lot below the waist, so I’ll most likely end up getting them tailored so they fit above my hips more properly.

If you’re into the dressed-up shorts look, I’ve included several pairs that caught my eye in the slider below. Most shorts in fabrics other than denim are more guaranteed to fit because there’s more stretch to them, in my opinion.


Levi's 501 Original Womens Shorts in Wise Up Black, High-Waisted Denim Shorts Outfit, Tilden of To Be Bright

Lastly, these black denim shorts truly shocked me in the sense that I honestly felt like they were MADE for me. Levi’s is one of those brands where every piece of denim, no matter if it’s the same style jean, fits differently on me. I’ve ordered denim in all sizes just trying to figure out what works on my frame because they’re all SO different. I tried this size 28 pair on & I couldn’t believe they fit me so perfectly, and on the first try too!

These shorts aren’t as high-waisted as the first denim pair but they hit right below the belly-button. If you wanted to cinch a belt on to hold them up in place, that works too. Personally, I’ve worn them with crop tops (as seen above) & bodysuits the most. For the record, a lot of people caught wind about how great this pair of 501 Original Shorts is and consider finding it in-stock in your size a stroke of luck. However, it does come in a longer, mid-thigh version & below I’ve included similar pairs from reputable brands I love my pairs of jeans from. And again, remember you can always return them if they don’t fit (for free!)