If there’s one fashion pairing that’s taken over the streets, social media feeds, and even our closets this season, it’s the iconic duo we never saw coming back so strong: ankle boots and leggings.
Yes, the effortlessly chic combination that defined casual-cool style a few years ago has returned, and it’s better than ever. From celebrities spotted in this comfy yet stylish ensemble to influencers showcasing endless ways to elevate the look, it’s clear the ankle boots-and-leggings trend is here to stay.
With endless styling options—think oversized sweaters, tailored coats, or edgy moto jackets—it’s the perfect balance of cozy and polished. Ready to find out how to rock this trend like a pro? Keep reading for all the tips and outfit inspo that will have you striding through winter in style.
1. Effortless All-Black Chic
This look is the epitome of understated elegance with an edgy twist. Start with a sleek pair of black leggings that fit like a second skin, paired with pointed-toe ankle boots to elongate the legs and add a sophisticated flair.
A high-neck black sweater provides a polished base, while an oversized black jacket adds volume and a touch of casual cool. Accessorize with bold, dark sunglasses and minimal gold jewelry to elevate the outfit further.
For a finishing touch, carry a small statement bag or camera-style crossbody to complete the street-style vibe. This ensemble is perfect for those looking to stay cozy while exuding effortless, all-black sophistication.
2. Cozy Street Style with a Luxe Twist
This outfit combines comfort and sophistication, making it perfect for an outdoor café date or a casual stroll through the city. Start with classic black leggings for a sleek and versatile base, paired with chunky tan platform ankle boots to add a trendy and cozy vibe.
Layer a long, tailored gray coat over a chunky black scarf and a lightweight sweater for a chic, layered look that keeps you warm. Add a touch of elegance with cat-eye sunglasses and minimal jewelry, such as gold rings or hoops.
The white socks peeking out above the boots add a playful and relaxed contrast, while the structured black mini bag completes the outfit with a refined edge. This ensemble perfectly balances practicality and effortless style for cooler days.
3. Classic Meets Contemporary with a Tailored Edge
This outfit combines polished tailoring with casual essentials for a look that’s both stylish and approachable. Start with sleek black leggings for a streamlined silhouette, paired with chunky black leather ankle boots that add a modern, edgy touch.
Layer a cozy oversized gray turtleneck sweater for warmth and comfort, then top it with a structured plaid blazer for a tailored, classic vibe. Bold accessories like neon earrings and statement sunglasses inject a playful twist into the look, while a structured black handbag with gold accents adds a luxurious feel.
Perfect for everything from brunch to an art gallery visit, this outfit effortlessly blends sophistication with streetwear-inspired flair.
4. Urban Cool with a Cozy Twist
This outfit strikes the perfect balance between edgy and cozy, making it ideal for city strolls or casual outings. The black leggings create a sleek, versatile foundation, while chunky black leather Chelsea boots with a lug sole bring an urban edge.
A gray oversized hoodie adds a laid-back vibe, layered with a classic leather jacket for a polished yet effortless look. The soft, oversized gray scarf and matching knit beanie add a touch of warmth and texture to the ensemble.
A structured black mini handbag elevates the outfit, while dark sunglasses complete the city-chic aesthetic. With a coffee cup in hand, this look is both practical and undeniably stylish.
5. Sophisticated Layers with a Modern Edge
This outfit exudes casual sophistication with a focus on timeless layering. The black leggings offer a sleek and versatile base, while chunky black Chelsea boots with a lug sole add a bold, modern touch.
A classic white tee provides a crisp foundation, topped with a tailored gray oversized jacket for structure and warmth. Draped effortlessly over the shoulders, a matching gray knit sweater adds a cozy, layered effect.
Minimal accessories, like dark sunglasses and a structured black crossbody bag, lend a polished, city-ready vibe. Perfect for anything from shopping to coffee dates, this look is equal parts chic and functional.
6. Cozy Shearling and Leggings for a Winter-Ready Look
This outfit is the perfect mix of warmth and style, making it a go-to for chilly days. The black leggings create a sleek, slim base, paired with beige platform ankle boots for a cozy yet trendy touch.
The oversized shearling-lined brown aviator jacket is the star of the look, offering both insulation and a luxurious texture. A white knit beanie and matching scarf add a soft, winter-ready feel, balancing the rich tones of the jacket.
The addition of visible white socks adds a playful layer of contrast while keeping the outfit casual. With this ensemble, you’ll stay snug without sacrificing style—ideal for running errands or enjoying a relaxed outdoor stroll.
7. Sleek and Sophisticated Ensemble
This outfit showcases how leggings can be elevated to a high-fashion statement. The black leggings are seamlessly paired with pointed-toe stiletto ankle boots, creating a sleek and elongated silhouette.
A tailored black blazer with a cinched waist adds structure and sophistication, making this ensemble ideal for a polished, city-chic vibe. Minimal accessories, such as oversized sunglasses and a structured black leather bucket bag, keep the focus on the outfit’s clean lines.
With its all-black palette and sharp tailoring, this look exudes confidence and elegance, perfect for business meetings, urban errands, or a stylish day out in the city.