Street Style: What to Wear With a Denim Skirt

Street style jean skirt outfit with high heels
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The Best Jean Skirt Outfits from Street Style

How to wear a jean skirt in every season
Learn how to style a jean skirt for every season. Kirstin Sinclair/Getty Images

Denim skirts are wardrobe essentials — but do you know how to style them to look up to date? Get inspired to create cute jean skirt outfits with these street style fashion photos, including tips on how you can customize each look to make it your own.

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City Chic Denim Skirt Outfit

City chic denim skirt outfit. Kirstin Sinclair

Here's a stylish denim skirt outfit you could wear to work, and then into the cocktail hour. Check out how chic this button-front denim skirt looks, when paired with a pretty bow blouse. High-quality, colorful leather accessories brighten the entire outfit and make it look pulled-together.

Tip: Wear this outfit with sheer tights and a classic coat in cooler months, as pictured. In spring and summer, it will look great with bare legs, and ballet flats or strappy sandals.

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Two Tone Jean Skirt

Street style woman in two tone jean skirt
Melodie Jeng/Getty Images

Two tone denim is super trendy now, and a jean skirt in different colors will add something special to your wardrobe. Wear it with a chambray top, as pictured here, for a stylish denim on denim outfit that can take you everywhere from shopping with friends, to running errands in the city. Wear with simple sneakers, for a stylish, unfussy look.

Tip: Tying on a scarf is a great way to add visual interest to this outfit.

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Denim Mini and White Cotton Shirt

Jean skirt outfit with white shirt
Casual chic in a white top and denim skirt. Marilyn Smith/Getty Images

Nothing says effortless style like a denim cut-off mini-skirt. For a breezy outfit you can wear shopping, sight-seeing and out to lunch, pair a short jean skirt with a light-weight cotton or linen button-up tunic. Wear the top untucked for a cool, long-over-short look and personalize the outfit with your favorite accessories.

Tip: A fedora hat and strappy sandals transform an easy top and skirt into a perfect beach vacation outfit.

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The Denim Midi Skirt

Woman in jean skirt outfit
Mauricio Santana/Getty Images

The midi length denim skirt, which hits your leg around the mid calf, is back in fashion. Wear it to create a pretty, bohemian look, with a soft ruffled blouse. To avoid a little house on the prairie vibe, keep your outfit on the modern side with a bold statement necklace, and easy sneakers.

Tip: When shopping for a longer denim skirt, look for a style with a front slit, as pictured here, which offers more freedom of movement.

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Skirt and Sweater Outfit

Jean skirt outfit on street style star
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Create a playful spin on a classic collegiate look, when you tuck a cute striped sweater into a denim cut-off mini skirt.

Tip: Simple sneakers, sunglasses, and a cute little purse are all you need to dress up this casual look for going out.

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Pleated Jean Skirt

Street style woman in pleated jean skirt and tweed jacket
Christian Vierig/Getty images

Create a playful outfit with a cheerleader style pleated denim skirt. You could easily wear this skirt with a simple white tee in the summer, for a youthful casual look. We love the grown up styling pictured here, though. This street style star dresses up her flared jean skirt with a ladylike tweed jacket, a serious black purse, and high heel statement sandals.

Tip: You can look polished in a shorter jean skirt, by covering up more on top, to create visual balance.

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Warm Up a Denim Mini Skirt With Faux Fur

Denim mini skirt outfit
Add a furry vest and tights to a jean mini skirt for winter. Pablo Cuadra/Getty Images

If you don't want to put away your denim mini-skirt for fall and winter, here's how to style it for the cooler months, with tights and faux fur.

Tip: Add a big, colorful leather bag to inject some fun into neutral or monotone winter outfits.

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Wear Denim With Army Green

Wear Denim With Army Green. Meldoie Jeng

Sharply cut, dark wash denim has become the fabric of choice for designers wanting to make a new style statement. Here, a denim skirt outfit is personalized with a trendy army-green spring coat and socks under sandals.

Tip: Swap the shoes pictured here for a pair of black high heel pumps, and you could easily wear this outfit almost anywhere except (for most of us) work.

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Upgrade a Denim Maxi Skirt With a Jacket

Long jean skirt outfit
A denim maxi skirt looks chic with a tweed jacket. Kirstin Sinclair/Getty Images

You may think of the denim maxi skirt as a casual, bohemian item. As pictured here, though, it can be easily styled to look chic for city wear, when you layer on a Chanel-inspired tweed jacket, black accessories and delicate jewelry.

Tip: Watch your proportions when layering pieces over a longer skirt. A jacket that hits around the top of your hip bones or higher will look best.

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Try a Skirt Instead of Jeans

Try a Skirt Instead of Jeans. Vanni Bassetti

Sometimes, style is just about doing something slightly unexpected. Here's how to tweak your usual casual-day outfit of jeans and a sweatshirt, to make it look a bit more pulled together. An easy jean skirt in a just-past-the-knee length is surprisingly right with a dark sweatshirt and boyfriend jacket, with a high-quality envelope tote adding fashion.

Tip: Loafers, sneakers or ankle boots give this look a boyish vibe that suits this day-off ensemble.