How to Wear an Updated Denim Skirt

Do you love a jean skirt as much as I do? The only problem is the look can quickly veer into not modern/age-appropriate/cool territory very quickly. Even I feel a little bit unsure of myself sometimes when putting together outfits with a jean skirt. Oh wait, I’m supposed to be calling it a denim skirt now. Like how a fanny pack is now a belt bag. Uh huh.

The first step is to find the right shape of denim skirt. Want something new and exciting? Go with the vintage look soft a-line. Younger or have great legs? Try a shorter version. Want classic? A slightly past the knee, straight version of the denim skirt will do for you. Two keys to keeping the denim skirt adult is to always add a chic topper (or a big necklace if it’s super hot!), and interesting shoes that will take advantage of the skirt’s blank canvas. We made three outfits at three different price points to demonstrate how a white t-shirt and jean skirt can be a super chic weekend look.

What’s your favorite way to wear a jean skirt? Which of the outfits below do you like best? Let us know!

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P.S. I’ve had the same Habitual jean skirt for like 10 years. I think this is the year I let Kyle decide if I keep it and wear it or tell me to buy a new one!

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3×1 / Jason Wu Denim Pencil Skirt, $265

Ace & Jig Quilted Coat, $598

Jenni Kayne Crepe Tee, $165

James Chan Suzy Bow Slide Sandal, $188.95

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J.Crew Button-Front Denim Skirt, $79.50

Madewell Print Robe Jacket, $98

ATM Schoolboy Cotton Crewneck Tee, $85

Madewell Addie Slide Sandal, $88

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H&M Knee Length Denim Skirt, $34.99

Caslon Twill Shirt Jacket, $79

Amour Vert Leif Slub Tee, $42

Treasure & Bond Mere Flat Slide Sandal, $59.95

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Lani Inlander is a personal stylist who has been working with clients who want to feel their best and look put-together every day for over 15 years. You can find her in the Washington, D.C. and New York metropolitan areas. Learn how you can train with Lani to become a personal stylist at The Stylist Studio

You can find Lani Inlander and Real Life Style on Facebook, LinkedIn, Twitter, Pinterest, and Instagram.


Real Life Style is a style consulting firm that teaches busy women to wear their power so they can live their lives fully and confidently. Lani Inlander, Kyle Dunphy and Sloane True are based in the Washington, D.C., metropolitan area and serve clients nationwide. We offer personal styling services, and an on-demand e-course.

Once in a while, you can find Lani Inlander and Real Life Style on Facebook, LinkedIn, Pinterest, and Instagram. Mostly, they are happily busy serving their fabulous clients, not hanging out online!