The Best Summer Skirts — and How to Style Them

Date: May 8, 2024

Skirts get their well-deserved moment in the style spotlight during the spring and summer. It’s the season for bare legs and easy, breezy dressing, and skirts are the perfect solution to your warm weather styling woes. They allow you to wear your favorite tops and blouses in a different way and experiment with proportion and silhouette. You can go bodycon or boho, casual or dressy, all in the same week.

A woman with long brown hair is wearing a navy sleeveless top and a blue and white striped skirt while standing outdoors on a sunny day. She is looking to the side with a thoughtful expression and has her hands lightly clasped in front of her. This outfit features one of the best skirts for a stylish look.

Treat skirts the same way you would your favorite pair of jeans, trousers, or even sweatpants. Skirts look great at the office, at happy hour, and while hanging out with the kids on the weekend. However, because there are so many different skirt styles, it’s easy to get overwhelmed by the many (many, many) options.

Every Trendsend box, whether it’s a theme box or your monthly curation, is a balance of goes-with-everything basics, layering essentials, and trendier pieces to encourage you to try something new. If a skirt shows up in your box, know that your Trendsend stylist personally picked it out just for you, and added a thoughtful selection of tops and jackets to wear with it and make styling and layering a breeze. Our stylists know their way around the best skirts, no matter the season.

How to Style a Denim Midi Skirt

The denim midi skirt and denim pencil skirt has been the unsung hero of the last few years. Depending on how you style it, it can be sleek and chic or ‘70s hippie cool — or a blend of both! For a simple and sophisticated vibe, pair it with a slim black sleeveless top with a high neckline.

A woman with her hair tied back is wearing a sleeveless black top and one of the best blue denim midi skirt with a front slit. She is smiling and holding a small checkered bag over her shoulder, and she is wearing tan wedge sandals.

To channel the ‘70s, wear your denim skirt with a printed blouse or a loose sweater and high boots. On the weekend, go casual in a cute knit tank and crossbody bag.

If you’re worried about the length of the skirt hitting at an awkward spot on your calf, add height with a heeled clog or chunky loafer.

How to Style a Mini Skirt

Don’t be afraid of the mini skirt! It’s a classic style that works for everyone; you just have to find your fit. If you’re leggy, you can basically wear any length you like, but if you prefer more coverage, try something that hits at a few inches above the knee. We love a cargo mini skirt in the summertime, as it gives “grown-up summer camp” vibes and looks great with a casual tee or tank, comfy sandal, and a cardigan or lightweight knit sweater layered over the top.

A woman with short blonde hair is wearing a white t-shirt with green and blue stripes and one of the best denim skirt with front pockets. She stands in a stylish indoor setting with wicker chairs and wooden tables, wearing brown sandals.

To tone down the “mini” of it all, style with flat shoes like sandals and loafers and balance the shorter length of the skirt with more boyish tops like button-downs and slightly oversized T-shirts. For an elevated take on the mini, wear it with a sweater and loafer.

How to Style a Knit Skirt

A woman with long wavy hair wearing a white sleeveless top and a blue and one of the best white striped wrap skirt stands smiling. She is holding a woven straw handbag and wearing beige sandals.

You may be surprised at how versatile and functional a simple knit skirt can be. (Our fave is by Michael Stars.) Whether it’s a mini, midi, or maxi style, a knit skirt will quickly become the MVP of your summer wardrobe — and well into the fall and winter too.

There’s really nothing you can’t wear with a knit skirt, so think of it like you would a pair of jeans or black pants. One foolproof outfit formula we return to time and time again because it always works: knit skirt, tucked-in tank, jacket or sweater wrapped around the shoulders. A fitted long pencil skirt looks great with a chunky heeled boot and boxy, cropped top, while a light-colored skirt feels irresistibly crisp and summery when paired with a lightweight button-down shirt.

The best skirts for summer are those that make your getting-ready routine easy and fun. Ready to expand your styling horizons with the humble but oh-so-versatile skirt? We’ve got you!