how to wear a denim skirt

20 Best Outfit Ideas for How to Wear a Denim Skirt

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A jean skirt is a wardrobe staple!

Denim skirts are going through a resurgence. And midi and maxi lengths are the most current way to wear them. You may remember maxi length denim skirts from the 90s. It was a popular length worn by Phoebe on Friends. If that length feels impractical for your everyday life, you’re not alone in that. Denim midi skirts are a good alternative. A skirt that’s knee length or longer with a finished hem and no distressing can be dressed up with a blazer, button-down shirt, or sweater for a day at the office. Or dressed down with flip-flops and a tank top for a casual day out. 

A denim skirt is a hardworking piece that you can get so much mileage from since it’s easy to mix and match with a variety of tops. 

After looking in the stores for months, I finally found a denim midi skirt that I love. It’s high waisted and ends up functioning like a pencil skirt with its straight shape. The slit up the front keeps it from looking frumpy. I usually wear a size 12, but sizing up to a 14 gives me the perfect fit. 

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How do you wear a denim skirt over 40?

Wear a denim skirt over 40 in a way that makes you feel confident. If you don’t love showing your thighs, skip a denim mini skirt and choose a knee or midi-length skirt. Many women worry that they may accidentally wear a style that’s too youthful. Skip a skirt that’s very short and very tight and you’ll be fine. You also want to avoid looking frumpy, which is a risk if you choose a long denim skirt. Defining your waistline is a great way to prevent that. Tuck in your shirt, wear a belt, and push up or roll up your sleeves.  

There are so many different styles of jean skirts from a short denim skirt to a midi or denim maxi skirt. Choose a white denim skirt for the summer months. Or a blue or black denim skirt that you can wear all year long. Choose a darker skirt that’s knee-length or longer to wear in a professional setting. 

In this post, I’ll show 20 of the best ways to style a denim skirt for warm and cool weather. And a variety of different settings.

Denim skirt outfit ideas for warmer weather

Let’s take a look at some outfits you can wear in the summer months. Ready to dive in? 

1. With a white flutter sleeve top, cream belt, and ballet flats

Here’s a super simple look to recreate for work in the warmer months. Throw on a cotton tee that’s elevated by flutter sleeves. Add a neutral belt, a similar tone bag, and some nude ballet flats.

With a white flutter sleeve top, cream belt, and ballet flats

Skirt | Flats | Belt

The flutter sleeves, belt, and ballet flats elevate the look so you’ll feel appropriate to walk into a meeting in a business casual environment. 

2. With a ribbed tank top, leather flip-flops, and boyfriend button-down shirt

I wear this cotton boyfriend button-down shirt a lot. The other day I felt cool wearing it in the hot sun. When you wear an oversized shirt, you get sun protection but there’s room for air circulation. To make the proportions work on this outfit, wear the shirt open and over top of a fitted tank top. Roll up your sleeves to help define your waistline.

With a ribbed tank top, leather flip flops, and boyfriend button-down shirt

Skirt | Tank Top | Boyfriend Shirt in oxford blue | Bag | Flip-Flops

Leather flip-flops keep the look casual. 

3. With a black ribbed tank top, black leather belt, Adidas, and a belt bag

You can absolutely pair a slim-fitting tank top with a fitted midi denim skirt or maxi denim skirt.  Tuck the shirt in to highlight your waistline. This tank is a bit longer than a crop top, making it easy to tuck in. Wearing a body-hugging top and bottom, you may worry that it will show a belly pooch in the side view. I’m wearing a pair of high-waisted belly-supporting underwear and it does wonders for flattening my stomach.

With a black ribbed tank top, black leather belt, Adidas, and a belt bag

Skirt | Tank Top | Similar Belt | Adidas | Belt Bag

Tie the black top in with black Adidas tennis shoes.

4. A monochromatic look with matching brown accessories

Here’s the easiest way to wear your skirt. Match the color of your skirt to the color of your top for a chic monochromatic look. Then add matching sandals, a belt, and a bag. The accessories create a color story that’s cohesive and grounds the look so it makes sense to the eye. 

A monochromatic look with matching brown accessories

Skirt | Belt | Similar Belt Bag | Similar Shirt | Similar Sandals

5. With a white tank top, linen shirt, and matching brown accessories

Nothing is simpler than an outfit with a white tank top and white linen shirt paired with a good denim skirt. Tuck in the tank top and leave the linen shirt open, with the sleeves rolled up. There are a few things that make this look come together. First, I’m wearing statement sandals. The “V” shape of the thong toe strap points the eye to the end of the foot. The thin straps of the ankle wrap highlight the ankle without cutting the leg line off. I’ve chosen a braided leather belt which is having a resurgence again. The braiding adds texture which is visually interesting.  

With a white tank top, linen shirt, and matching brown accessories

Skirt | Tank Top | Belt | Similar Belt Bag | Sandals | Button-up Shirt

6. With a white Dolman sleeve top and matching brown accessories

Brown accessories are having a moment. The Dolman sleeve blouse I’m wearing is a bit more elevated than a basic tee. The cloth of the shirt adds some texture and visual interest thanks to some vertical crinkling. When you wear a looser top, tuck it in like I’m doing here. Adding a belt elevates the look. This is a look you could wear to a business casual workplace.

With a white Dolman sleeve top and matching brown accessories

Skirt | Belt | Similar Belt Bag | Sandals | Shirt in white

Swap the flat sandals out for brown ballet flats to make the look even more formal. 

7. With a white tank top, white sneakers, belt bag, and gray sweatshirt

Here’s another simple look that’s anything but boring. Tuck in your basic white tank top to define your waistline. The white of the sneakers plays off the white of the top. Throw a casual gray sweatshirt over your shoulders for chilly air conditioning. And add a belt bag for your phone and wallet and a casual feel.

With a white tank top, white sneakers, belt bag, and gray sweatshirt

Skirt | Tank Top | Belt Bag | Sneakers | Similar Sweatshirt

8. With an olive green muscle tee, and matching brown accessories

Brown and olive green look so good together. In this look, the olive green and brown draw in the eye and the blue skirt become a neutral backdrop. When you’re wearing a looser-fitting top, tucking it in defines your waist and keeps you from looking frumpy.

With an olive green muscle tee, and matching brown accessories

Skirt | Belt | Similar Sandals | Similar Belt Bag | Similar Shirt

9. With a black mock turtleneck top, black platform flip-flops, a black belt, and a tote bag

I will forever love a black mock turtleneck. Here I’m pairing it with black platform flip-flops, a black belt, and a black tote bag for an easy look. 

With a black mock turtleneck top, black platform flip flops, a black belt, and a tote bag

Skirt | Belt | Flip-Flops | Bag | Top

Jean skirt outfits for colder months

10. With a white tank top, denim jacket, nude belt, bag, and ballet flats

Denim on denim gets mixed reviews. You may love it or hate it. This look was an experiment and I was shocked by how good it looked. This denim jacket has a classic fit which creates the perfect proportions with the skirt since it hits right at the top of the hips. It’s also a tone darker than the skirt. Wearing different tones of denim keeps it from looking so matchy-matchy. 

With a white tank top, denim jacket, nude belt, bag, and ballet flats

Skirt | Flats | Belt | Tank Top | Denim Jacket

11. With a striped button-down shirt, a black belt, loafers, and a tote bag

This classic fit cotton poplin navy and white striped button-down shirt works in every season and with just about every bottom imaginable. I’ve tucked it in here and added a black belt, loafers and a tote bag for a preppy work look.

With a striped button-down shirt, a black belt, loafers, and a tote bag

Skirt | Belt | Loafers | Bag | Shirt

12. With a white tank, white blazer, nude belt, bag, and raffia slides

Here’s another work look. Pair your white blazer over top of a white tank top. I’m wearing this denim skirt in a size 14 and my bottom half is larger than my top half. Notice how this blazer creates equal proportions between my upper and lower half. Adding a nude belt helps to define the waistline and create an elevated look. These raffia slides with a metal buckle are more elevated but if you prefer a closed-toe shoe on cooler days, choose a ballet flat or pointy-toe flats. 

With a white tank, white blazer, nude belt, bag, and raffia slides

Skirt | Belt | Tank Top | Blazer | Slides

13. With a white tee, Breton stripe sweater, black Birkenstocks, belt, and belt bag

This is such an easy look. I’m pairing a white t-shirt with this denim skirt. And adding black Birkenstocks, a black belt, and a belt bag. The Breton stripe sweater is great to have if a chill sets in.

With a white tee, Breton stripe sweater, black Birkenstocks, belt, and belt bag

Skirt | Similar Belt | Belt Bag | Similar Sweater | Birkenstocks

14. With a white tank top, black Double-breasted blazer, cap toe flats, and tote bag

A black double-breasted blazer instantly elevates any look. But take note of the angling that occurs at the bottom button. The lapels of this jacket aren’t straight up and down, and that angle naturally helps to define the waistline. Black Chanel-inspired cap toe flats and a black rectangular tote bag make this look office ready. 

With a white tank top, black Double breasted blazer, cap toe flats, and tote bag

Skirt | Tank Top | Blazer | Bag | Similar Flats

15. With a chambray shirt and brown accessories

Brace yourself, here’s another denim-on-denim look. But this time with a chambray shirt. This shirt is a very similar shade to the skirt. And yet it works! Brown accessories add a second tone and visual interest. 

With a chambray shirt and brown accessories

Skirt | Similar Belt Bag | Similar Shirt

16. With a striped shirt and brown accessories

This navy striped ribbed shirt is perfect with this skirt. Just tuck it in, add some accessories and you have a really good-looking fall outfit. 

With a striped shirt and brown accessories

Skirt | Belt | Similar Sandals | Similar Belt Bag

17. With a cropped cardigan sweater, espadrille sandals, and a matching bag

This two-tone look is an easy way to create a sharp-looking outfit. The cropped fitted cardigan sweater matches the belt, espadrilles, and bag for a sharp look you could wear to work. 

With a cropped cardigan sweater, espadrille sandals, and a matching bag

Skirt | Belt | Espadrilles

18. With a black mock neck sweater, black loafers, belt, and tote bag

Since this skirt has a high waist and the sweater has a looser fit, I’m giving it a front tuck into a belted waistline to define the waist. Loafers and a tote bag make this a work-ready look for transitional weather.

With a black mock neck sweater, black loafers, belt, and tote bag

Skirt | Belt | Loafers | Bag

19. With a brown leather jacket, gray sweatshirt, and white sneakers

Here’s an edgy look you can wear for a casual date night. I love gray and this brown color together. If you’d rather wear a graphic t-shirt, try a t-shirt with the name of your favorite city on it. Add white sneakers and you have a cool look.

With a brown leather jacket, gray sweatshirt, and white sneakers

Skirt | Similar Sweatshirt | Sneakers

20. With a cropped cable knit sweater, brown belt, and taupe ankle boots

This taupe sweater pairs perfectly with these ankle boots. And the brown belt speaks to the brown in the heel of the ankle boots and of the crossbody bag. 

With a cropped cable knit sweater, brown belt, and taupe ankle boots

Skirt | Belt

The best way to wear boots with your midi denim skirt is to wear taupe ankle boots or skin-tone matching boots. They extend the look of your legs whereas black ankle boots chop up your leg line. 

Now there is an exception to that. If you have a black denim skirt, black knee high boots would be great with it to extend the look of your legs. You may also like a pair of cowboy boots with it if that fits your personal style. 

If you’re wearing a lot of high-waisted pieces, a sweater that’s short or almost cropped is easy to tuck in.  

infographic how to wear a denim skirt

Hi, Friend. I'm Marya. I'm so glad you're here!

I’m here to help women feel good inside and out through approachable everyday style inspiration and encouragement for midlife. Once upon a time, I worked as a therapist and coach. Now, I’m a holistic style blogger studying style coaching! Be So You celebrates leaning into who we were meant to be! 

Read about my  journey to self-discovery at 40. Follow me on Instagram here and Pinterest here. Send me a quick question through my contact page here.  

Fit Note: I’m midsized at 5’6″, 160 pounds, with size 12 jeans.

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