Because it’s a more elegant garment than jeans, knowing how to style a long denim skirt well means you’ll have countless stylish and comfortable outfits you can wear on repeat.
A fashion-editor favorite, jean skirts are both durable and feminine at the same time and look just as chic styled with sneakers as they do with heels. Unlike your basic pair of Levi’s, midi-length and long denim skirts can be dressed down with a bomber jacket or elevated in an instant with an evening coat.
And because they are so incredibly versatile, it’s no wonder jean skirts are constantly being reworked and brought back into fashion. Which is why finding a long denim skirt that fits your style—whether it be A-line, straight, or pleated—is a solid wardrobe investment. It is one of those pieces that fits in automatically with your existing closet, and most likely already goes with all of your favorite sweaters and tops.
That said, I’m always looking for new ways to wear my long denim skirt. With a piece as timeless as this, it helps to know how to pair it with the latest trends for something modern and cool. Below are some of the best outfit ideas I came across for this season and beyond.
With suede and casual stripes
A cute striped polo or T-shirt, as seen here, keeps a long denim skirt feeling playful while still as practical as ever. This look combines all the best fall and winter trends—a long shearling coat, brown leather boots, and suede in the form of a hold-all tote bag. Together they are the perfect example of elevated casual style. And if you want to take this outfit up a notch, swap in a gold-buckle leather belt and kitten-heel boots for a more polished vibe.
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With sexy accent pieces
This street style star shows exactly how to wear a long denim skirt in colder temperatures. The baggy sweater feels cozy, yet cleverly styling it with a belt creates a sultry silhouette that matches the vibe of a denim skirt with a high slide slit. A wool coat worn casually over the shoulders adds some dimension, while thigh-high boots bring the whole look together.
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Scandi-inspired
One of my favorite street style outfits from Copenhagen Fashion Week, this dark navy pleated denim maxiskirt looks so chic worn with a shirt and a tie in the trendiest print of the moment: tartan. The rolled-up sleeves keep this combo from looking too stuffy. With cold weather, I’d recommend trading the sandals for ballet flats or loafers and adding a blazer to maintain the formal finish. This look is ideal for the office and shows the versatility of this skirt style—it’s the kind of piece that can truly be worn year round.
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Old Navy Oversized Button-Down Boyfriend Shirt
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Go for double denim.
Proving that denim-on-denim can work, this maxiskirt outfit leans more into high fashion with its voluminous sleeves and A-line skirt. Look for a matching set, or try contrasting denim washes to break up all the blue. Shoes that stand out, like these silver metallic heels, make a divine footwear choice regardless. I recommend a classic beige trench coat for outerwear and a simple clutch to accessorize.
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Old Navy Button-Down Cropped Denim Shirt
Styled with silk
Boho is back, and this deep navy denim jacket and long jean skirt outfit manages to maintain a free-spirited feel with the addition of a ’70s-style head scarf and orange-tinted aviators. If you want to break up all the denim, swap the denim jacket for a bow blouse. In any season, denim is the ideal fabric to combine with lighter materials, especially when wearing a darker wash. We all love denim for its durability, but if you feel your outfit is ever looking too heavy, a pro-styling tip is to team it with textiles like lace, chiffon, or silk.
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With leather boots
While most skirts might leave you feeling chilly in fall, a denim midiskirt worn with knee or mid-calf boots will keep you both stylish and toasty once the temperatures drop. Stay extra warm by wrapping up in a wool coat and cashmere scarf, and don’t forget your oversized shades to complete this dreamy winter outfit.
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With straight lines and a crop top
Denim is mostly associated with casual outfits, but this ever so elegant ensemble shows that jeans work as cocktail attire if you keep the lines straight, clean, and tailored. The crop top works here, but you could also sub in a fitted white top and still look refined. It’s the slimline coat that really keeps everything elevated. Layering a fine knit cardigan for warmth is also an option, with a leather clutch being the only accessory needed for this sophisticated look.
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