What To Wear With High-Waisted Jean Shorts? 11 Top Trends & Styles

March 21, 2023
by Christine Devereaux

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Styles and trends are always changing and evolving, but one fashion staple we recommend having in your closet at all times is a pair of high-waisted jean shorts. 

These shorts can be styled in so many different ways, so they’re perfect for a wide variety of outfits and occasions.

The problem is that a lot of people don’t know how to style these shorts properly. 

If you’ve got a pair of high-waisted jean shorts that you’re struggling to style, or if you’re considering buying a pair but don’t know what to wear them with, this is the guide for you! 

We’re going to share our favorite options for what to wear with high-waisted jean shorts and help you to create flattering and timeless looks.

Style Ideas For High-Waisted Jean Shorts 

When thinking about how to style high-waisted jean shorts, you should consider what to wear on your top half as well as whether you want to add any other garments to your lower body.

Accessories and shoes should also be part of the overall look. 

Here are some ideas of what to pair with your high-waisted shorts:

Upper Body 

Here are a few ways to style your high-waisted jean shorts on the top half.

1. Crop Top 

High-waisted shorts are designed to accentuate your waist, so one of the best upper-body garments to pair them with is a crop top

Obviously, this is a more suitable outfit combination for summer since you won’t want to walk around in shorts and a crop top once the weather gets colder.

However, when it’s warm enough, we encourage you to try out this pairing. 

We get that wearing a crop top can feel a little daring depending on your level of body confidence, but high-waisted shorts will cover most of your midriff, so the crop top shouldn’t reveal too much in any case. 

2. Blouse

You can’t go wrong with a loose blouse when styling high-waisted jean shorts. 

All body shapes and sizes are beautiful, but we know that some people can feel insecure about having a pear-shaped figure, especially when wearing figure-hugging clothes. 

If this is the case for you, pairing a loose blouse with your high-waisted shorts can help to alleviate some of that self-consciousness by accentuating your curves and balancing out your top half at the same time. 

Just make sure to tuck your blouse into the waistband of your shorts so that you don’t lose the waist accentuation. 

3. T-Shirt 

For a more casual look, try wearing a t-shirt with your high-waisted jean shorts.

This look is perfect for the summer, and it can easily be dressed up with your favorite jewelry if you’re going somewhere exciting like a party or festival. 

The great thing about t-shirts is that they can be styled in a variety of different ways.

You can either tuck it in, or if the fabric has enough length, you could tie it in a knot at the front to turn it into a crop top!

4. Button-Up Shirt 

Just because you’re wearing jean shorts doesn’t mean you can’t create a classy outfit!

Just style your high-waisted shorts with a button-up shirt, neatly tucked into the waistband, and you’re ready to go! 

Button-up shirts come in a variety of styles, including long-sleeved, short-sleeved, or even sleeveless.

This means you can still wear the button-up shirt and high-waisted short combo whatever the weather. 

This look is especially cute when accessorized with some simple, elegant pieces of jewelry. 

5. Jacket 

If you’re wondering how to style high-waisted shorts when the weather is a little colder, we recommend a jacket, or a cardigan depending on your personal style. 

When you feel a chill in the air, it can be tempting to throw on a sweatshirt, but unless your sweatshirt is cropped, this means losing the waist-accentuating benefits of high-waisted shorts. 

Therefore, we recommend keeping warm with something that you can leave open at the front. 

Lower Body 

Now on to styling jean shorts with the lower half of your body.

6. Tights 

Want to wear your high-waisted shorts but also avoid getting cold? There’s a simple solution: tights! 

If you’ve never tried the high-waisted shorts and tights pairing before, you absolutely should.

It’s a game changer and allows you to show off your legs without sacrificing comfort as the weather gets colder. 

Depending on how cold the weather is, you could opt for thinner, skin-colored tights just to provide a little bit of extra warmth, or you could choose thicker, woolen tights for a more winter-friendly outfit. 

7. Knee Socks 

If you just can’t get behind wearing shorts with tights (it’s not everyone’s cup of tea) we have an alternative suggestion - knee socks. 

Knee socks look great with high-waisted jean shorts because they showcase your legs even more than tights but they also provide a good middle ground when it comes to warmth. 

Two girls wearing high waisted jean shorts

Accessories And Shoes 

8. Belt 

Since, as we mentioned earlier, the main benefit of high-waisted shorts is that they make your waist look shapely and help to create an hourglass shape, we always recommend accessorizing your shorts with a belt. 

Depending on the size of the belt loops on your shorts, you might be limited to a particular belt width. However, all belts can look good with high-waisted shorts. 

On the one hand, a thinner, plainer belt will add to the waist accentuation without distracting from the rest of your outfit.

On the other hand, a large, statement buckle can really take an outfit to the next level. 

9. Heels

If you’re going out for the night, you can easily dress up your high-waisted jean shorts with a pair of heels. 

Heels look especially classy with shorts and a button-up shirt or blouse, but you can also wear this type of footwear on a night out with a crop top and a jacket. 

10. Sandals 

For the summer, pairing your high-waisted jean shorts with a cute pair of sandals is a no-brainer. 

Styling outfits with sandals is so much fun because sandals come in so many different styles.

From flip-flops for casual beach wear to gladiator sandals for a more elaborate look, you have a lot of options for making your outfit unique and suited to you. 

11. Boots 

When it’s colder out, or for muddier terrain where sandals or heels wouldn’t be suitable (think festivals, woodland walks or pumpkin patches) a pair of boots can look great with high-waisted jean shorts. 

For a festival, we love the combination of high-waisted shorts, your favorite band t-shirt (or a crop top) and a pair of lace-up boots. 

Boots, including heeled boots, also work well if you’re going to pair your shorts with a pair of tights or knee-socks since socks and sandals are a no-go and not all heels are meant to be worn with visible socks or tights.

Final Thoughts 

We hope that our guide has provided you with some fashion inspiration when it comes to styling your high-waisted shorts in a way that looks and feels great.

No matter your body type, personal style, or hometown climate, you can make high-waisted shorts work for you by choosing the right choice of top, shirt, or blouse as well as socks, tights, footwear, and accessories. 

Don’t be afraid to experiment and try new styles, including pairings not mentioned in this article!

Fashion should be fun and if you feel comfortable and confident, that’s all that matters at the end of the day.

Related: The 7 Best Jean Shorts For Thick Thighs [Thick Thighs Save Lives]

About the Author
Christine Devereaux is a style and gear junkie. She loves the outdoors and picking out clothing and home goods for her husband, son and dog.
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