Flared leggings are the perfect mix of cute and comfy, offering all the stretch and softness with a slight flare that instantly elongates your legs. Universally flattering and versatile, you can style flared leggings with anything from cozy winter looks to chic and edgy Adidas Samba outfits. In this round up, I’m sharing 13 outfit ideas for every season so you can see just how effortlessly this wardrobe staple works year-round.
How to Style Flared Leggings
Before we jump right into the flared leggings outfits, we’ll be breaking down what flared leggings actually are, and why they deserve a spot in your closet. This post is your go-to guide for learning how to style flared leggings in ways that feel fresh but on-trend, and practical with any budget.
What Are Flared Leggings?
Flared leggings are similar to classic leggings, but are fitted with a slight flare at the hem. Unlike regular leggings, which keep a snug fit from waist to ankle, flared leggings hug your hips and thighs before suddenly widening from the knee down. This small design adds movement, balances proportions, and creates the illusion of longer legs.
What to Wear With Flared Leggings
- Cropped Vests: A perfect pairing for flared leggings, lightweight quilted or puffer style vests add warmth and shape without hiding your waistline.
- Jackets: Whether you choose a structured denim jacket, a tailored wool coat, or a fuzzy sherpa, the different materials and lengths add texture and dimension to flared leggings.
- Bodysuits: Stretchy cotton blended or ribbed knit bodysuits create a smooth, fitted base that tucks seamlessly into flared leggings for a clean, elongated look.
- Turtlenecks: Turtlenecks, especially in lightweight knits, pair effortlessly with flared leggings for a chic, elevated look.
- Cropped Layers: The shortened, cropped cuts of camis or sports bra tanks keep proportions balanced with flared leggings, making them a perfect option for warm weather or layering underneath jackets.
- Boots: Cozy ankle boots or suede Chelsea boots both work beautifully with flared leggings. Their sturdy structure contrasts the softness of flared leggings while keeping the flare visible.
- Sneakers: Classic canvas hi top sneakers or platform styles both add comfort and a casual edge against the simplicity of flared leggings for everyday wear.
How to Wear Flared Leggings
Turtleneck Sweater and Houndstooth Flannel Jacket
Khaki flared leggings create a soft, neutral base that pairs perfectly with a cropped knit turtleneck sweater. Layer on a houndstooth flannel jacket for a pop of pattern, and ground out the look with matching Chelsea boots.
Double Breasted Coat and Hoodie
Set the stage for a casual, street-ready vibe by layering a structured coat over a hoodie. Just add a saddle bag and some Converse for a cute and easy outfit to style with flared leggings.
Puffer Vest and Cropped Long Sleeve
Shop this Amazon Outfit Here (this vest has since sold out, shop here for a similar style)
Create a comfy but cute base by layering a brown cropped puffer vest over a cropped long sleeve. The duo creates a flattering silhouette against flared leggings. Lean into the cozy look and finish off with these UGG-lookalikes.
Mock Neck Top and Cropped Puffer Vest
Stay warm with a mock neck long sleeve layered under a matching puffer vest. It’s a last-minute combo you can style with flared leggings that look intentional. Just don’t forget to slip on some cute and comfy ankle boots to bring the outfit together.
Zip Up Cardigan and Hi-Top Sneakers
Shop this Amazon Outfit Here (Some items have since sold out, shop here for a similar style jacket. Shop here for a similar style cami)
Style your flared leggings with a cropped cami for a cute and simple base, then layer on a soft knitted zip-up jacket for a chic but relaxed feel. I love to round out the look with some designer-inspired sneakers, perfect for a quick coffee run on a breezy day.
Oversized Crewneck and White Puffer Vest
Shop this Amazon Outfit Here (this crewneck has since sold out, shop here for a similar style)
Layer on a white puffer vest over a black oversized crewneck for a chic contrast against flared leggings. Pair the look with sneakers and a saddle bag to keep things equally cute and low-key.
Zip-Up Hoodie and Crop Tank
Shop this Amazon Outfit Here (this tank has since sold out, shop here for a similar style)
Go for soft neutrals with a khaki zip-up hoodie layered over a white crop tank. This combo is great to style with flared leggings and sneakers when you need something cute for an active day out during fall or spring.
Button Down and Platform Sneakers
For a sleek, minimal base, style flared leggings with a buttery soft cropped cami. Pull on a comfy waffle knit button down for texture, and then add some extra height with these trendy platform sneakers.
Scoop Neck Top and Cropped Vest
A pair of flared leggings against a scoop neck long sleeve strike a perfect balance between fitted and flattering. Pair them with a puffer vest for extra warmth. Finish off the look with comfy sneakers for a cute, everyday look on chilly days.
Sport Tank and Denim Jacket
Build a streamlined, sporty base with a cropped sports tank and high-waisted flared leggings. Throw on a relaxed fit denim jacket for a classic, structured layer. For a cute and trend-savvy look, add some HOKA sneakers to the mix..
Sherpa Jacket and Bodysuit
A fitted turtleneck bodysuit paired with flared leggings created a sleek, tailored base. Pull on a cute and fuzzy sherpa jacket and suede clogs to bring in all the chic and cozy vibes.
Quartzer-Zip Sweater and Cropped Jacket
Shop this Amazon Outfit Here (this scarf has since sold out, shop here for a similar style)
If you’re spending an active winter day outside, a comfy pair of flared leggings styled with a fitted mock turtleneck and sneakers sets a casual chic tone. Layer it up with a quarter-zip sweater and cropped puffer jacket to stay warm while still looking stylish. Add some cuteness to this cozy look with a soft houndstooth scarf.
Square Neck Sports Tank and Sneakers
Shop this Amazon Outfit Here (Some items have since sold out, shop here for a similar style tank. Shop here for similar style sneakers)
Style high-waisted flared leggings with a square neck sports tank for a cute and sleek summer workout look for hot days. The fitted, double-layer design of the top keeps things supportive while still looking cute. Top it off with your fave sneakers for a stylish throw-on-and-go look.
Style Your Flared Leggings into Chic Outfits All Year
I love how flared leggings check all the boxes. They’re flattering, comfy, and endlessly versatile. If you need more fashion inspo in your life, follow me on Instagram for the latest trends—and don’t forget to shop all my cute, budget-friendly looks on my Amazon storefront.
