Denim Skirt Outfit

From Classic to Edgy: How to Wear a Denim Skirt in 2023

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To your pleasant surprise (or demise) the long denim skirt is back in style! And though I don’t report on trends a lot (because I believe classic fashion trumps trends), I do like to highlight the clothing pieces where classic fashion and trends intersect. Case in point: the denim maxi skirt. Whether they remind you of middle school (in a bad way), or you feel excited to break out this piece once again, denim skirts have been around for years and continue to be a fashion staple. And though a denim mini skirt may seem more fun and playful, some of the best denim skirt styles have a high waist and a knee-length or longer hemline. This will elongate your legs and create a flattering silhouette. Now, how can you argue with that? Read on to discover your new favorite ways to wear a denim skirt!

1. With a Denim/Chambray Shirt and Belt

how to wear a denim skirt

shirt | skirt | belt | shoes | tote | earrings

There’s a reason double denim or the Canadian tuxedo has been around for so long. Not just because it’s controversial (though it is), but because it just works. It’s a casual look that makes a great starting point for your personal style to shine.

Pair your ensemble with mules for a casual chic look, sneakers for an easy yet stylish look, or cowboy boots for something trendy – yeehaw! This denim skirt outfit is perfect for a casual look that can be dressed up or down depending on the occasion. Don’t forget to add a belt, as that breaks up all the blue and highlights your waist.

2. With a Button-Down Shirt

how to wear a denim skirt with a button down shirt

shirt | skirt | shoes | bag | earrings | necklace

For a polished look, consider pairing your denim skirt with a button-down shirt. A crisp, white button-down can create a clean and sophisticated ensemble that looks good on any body type.

Tuck the shirt into the skirt to accentuate your waist. You can also add a blazer for a professional touch or throw on a denim jacket for a more casual vibe. If you prefer a more relaxed look for the summer, pair your skirt with stylish sandals. This is perfect for a weekend brunch or a day out with friends!

3. With a Basic T-Shirt, Sneakers, and a Baseball Cap

how to wear a denim skirt

tee | skirt | sneakers | hat | bag | necklace

Probably the most comfortable and easiest way to wear a denim skirt is with a basic t-shirt and a pair of sneakers. This look is perfect for a casual day out or for running errands.

For the top, opt for the classic white t-shirt because it’s timeless and stylish all at once. Tuck the shirt into the skirt or do a half-tuck for a more relaxed vibe. To complete the look, slip on your favorite pair of sneakers (minimalistic ones are a good choice) and a baseball cap to keep the sun out of your eyes. If you want to add some extra flair to this outfit, accessorize with jewelry and a crossbody bag.

4. With a Striped Shirt and Sandals

how to wear a denim skirt with a striped shirt

tee | skirt | sandals | bag | earrings

File this look under outfits you can’t go wrong with. The combination of the denim and stripes creates a perfect balance between casual and sophisticated, making it an ideal outfit for both a day out with friends and a date night.

To achieve this look, you can choose a fitted or loose striped shirt depending on your style. For footwear, you can opt for leather sandals or espadrilles to achieve an effortless and comfortable look. Overall, wearing a denim skirt with a striped shirt and sandals is a classic combination that you can always count on to look stylish and put together. With these pieces, you’ll have a versatile and timeless look that can be worn from season to season!

5. With a Blazer and T-Shirt

how to wear a denim skirt with a blazer

tee | blazer | skirt | loafers | necklace | sunglasses

For a more polished and sophisticated look, try pairing your denim skirt with a blazer and t-shirt combo. This ensemble is perfect for a day at the office or a casual night out with friends.

To start, choose a blazer in a solid color, such as black or navy. This will give you a classic and timeless look. Next, opt for a simple t-shirt in a neutral color, like white or gray. You want the t-shirt to be slightly loose and flowy to balance out the structured blazer. (Or vice versa.) When it comes to accessorizing, keep it simple and subtle. A classic watch, sunglasses, black leather tote, or gold jewelry will add the perfect finishing touches to your outfit.

6. With a Cardigan

how to wear a denim skirt with a cardigan

cardigan | skirt | flats | crossbody | hoops

The cardigan has always been a wardrobe staple and it pairs beautifully with a denim skirt. Opt for a cardigan in a neutral shade like black, beige, or white, and style it with your denim skirt. This combination looks fantastic when paired with heels or chic ballet flats.

If you prefer a more casual look, you can style your cardigan with a denim skirt and a pair of white sneakers. The great thing about a cardigan is that it is versatile enough to work with any denim skirt length, from mini to midi to maxi. Don’t hesitate to experiment with different lengths and styles to find your perfect combination!

7. With a Moto Jacket

how to wear a denim skirt

cami | jacket | skirt | boots | earrings

If you’re looking for a way to add a bit of edge to your denim skirt look, consider pairing it with a moto jacket. A leather moto jacket is the perfect addition to a denim skirt outfit, especially if you’re going for a more casual, rocker-inspired vibe.

To elevate this look for date night, pair it with a satin or silk cami. The combination of feminine plus edgy creates an eye-catching contrast. Finish off the look with ankle boots – these are the perfect balance between elevated and casual. Overall, pairing a denim skirt with a moto jacket is a great way to mix classic and modern style elements, creating a look that’s both timeless and trendy.

8. With a Turtleneck, Camel Coat, and Tall Boots

how to wear a denim skirt with knee high boots

turtleneck | coat | skirt | boots | hoops

Need an outfit for the colder months? You’ve got it. When the weather gets colder, it can be hard to figure out how to style your denim skirt while staying warm. You don’t have to figure it out for too long, however, because pairing it with a turtleneck, camel coat, and knee-high boots will keep you as stylish as it does cozy.

For this look, opt for a fitted turtleneck in a neutral color like black or cream. Tuck it into your denim skirt for a chic silhouette. Layer on a camel coat, which is both classic and luxe, and will add warmth without weighing you down. As for footwear, tall boots are the way to go. Whether they’re knee-high or over-the-knee boots, they will elongate your legs and provide additional warmth for the cooler days. Choose a pair in a complementary color, such as black or brown.

9. With a Tank Top and Sandals

how to wear a denim skirt with a tank top

tank | skirt | sandals | bag | necklace

As the weather heats up, one of the easiest ways to wear a denim midi skirt is with a simple tank top and a pair of sandals. This casual and effortless look is perfect for a day out with friends or a trip to the beach.

When it comes to sandals, there are endless options. Flat sandals are perfect for a laid-back vibe, while block heels can dress up the look. Strappy sandals and espadrilles are all stylish choices to consider too. To finish off the outfit, accessorize with simple jewelry and a straw bag. After all, nothing quite screams “summer” like a straw bag!

10. With a T-Shirt, Cardigan, and Sandals

how to wear a denim skirt

tee | skirt | cardigan | sandals | tote | earrings | necklace

This outfit is perfect for transitional dressing and for the warmer months that still have chilly days. (Spring in Iowa, I’m looking at you.) The longer denim skirt adds more leg coverage while the sandals show off your pedicure.

The cozy cardigan will keep you warm on cooler days and add a touch of sophistication to your look. Plus, if the sun comes out, you can easily shed it to reveal your classic t-shirt. This is a stylish and casual outfit that is perfect for a casual Friday or getting brunch with friends!

These jean skirt outfits are just the beginning! You can wear it with a graphic t-shirt for an edgy casual look, a crop top for something young and trendy, or even high heels for the office or date night. It’s a simple piece that has serious styling power. So why not give your favorite pair of jeans a break and invest in a good denim skirt?

Psst – Do you want an outfit cheat sheet so you can always have stylish outfits to fall back on? I’ve got one for you here, with a lot more fashion freebies!

Blazers pair so well with denim skirts. For fresh ideas on how to wear one, keep reading: New Ways to Style Your Basics | 14 Blazer Outfit Ideas

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Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making mychicobsession.com a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.