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How to Wear Boots

Get the most style out of your favorite pairs, from ankle to thigh-highs!
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If we subscribe to any style rule, it’s this one: You can never have too many pairs of boots. However, when you start to build your collection, figuring out how to wear boots well can be a bit tricky. Luckily, we know a thing or two about outfit matchmaking. Read on for a few tips and tricks to get the most wear out of your favorite pairs.

How to Wear Ankle Boots

Ankle boots are the perennial style MVP. Equal parts polished and nonchalant, they slip seamlessly into just about any outfit equation. For daytime ease, think cropped jeans and a slouchy, oversized cardigan. When the mood shifts dressy, swap in a midi skirt or a floaty dress; ankle boots ground the look with just enough structure to keep things interesting. They’re the kind of piece that doesn’t flinch at a seasonal transition – bare legs in spring, tights in fall, always chic. The takeaway? Ankle boots don’t just go with everything, they elevate everything.

How to Wear Mid-Calf Boots

Mid-calf boots walk the line between classic and contemporary, making them a smart staple for everyday wear. They pair beautifully with midi skirts – especially when there’s a bit of movement in the fabric – and create a clean, elongated line when worn with skinny jeans. For layers, think contrast: an oversized sweater adds softness and ease, while a tailored blazer sharpens the whole look. It’s a silhouette that works from weekday errands to weekend brunch, with just enough edge to keep things interesting. Consider them your shortcut to looking pulled-together, even when you’re not trying.

How to Wear Thigh-High Boots

There’s a fine art to styling thigh-high boots without veering into costume territory – and it starts with smart layering. A mini skirt and thigh-highs might sound bold, but add a chunky knit and a tailored coat, and suddenly it’s street-style gold. Prefer something more streamlined? Try fitted jeans and a turtleneck under a sweeping wool coat – the boots do the talking, while the rest of the look keeps it cool and composed. For colder days, tights or textured socks add both interest and insulation to a chic little sweater dress. The result? A look that’s confident, contemporary, and completely wearable.

How to Wear Winter Boots

Cold-weather boots don’t have to mean sacrificing style for function. In fact, the right pair can do both beautifully. Think faux fur-lined or lug-sole styles that bring texture and edge to your winter wardrobe. Pair them with a chunky sweater dress and thermal leggings for a look that’s cozy and composed. A puffer coat adds volume and warmth, while a soft knit scarf ties it all together (literally). It’s the kind of outfit that makes braving the chill feel like a fashion-forward choice, not a compromise.

How to Wear Chelsea Boots

Few shoes flex as hard as the Chelsea boot. One day it’s grounding a romantic midi dress, the next it’s sharpening up a pair of cropped trousers and a boxy blazer. Their clean lines and pull-on ease make them a go-to for everything from coffee runs to client meetings. Straight-leg jeans or a shift dress? Always a yes. Add a pair of patterned socks or ribbed knits for a flash of personality that doesn’t overpower. Season after season, Chelsea boots prove they’re not just versatile – they’re essential.

Shop for Your Next Pair of Boots at Anthropologie!

From bold to classic, our boots are anything but basic. Shop the collection and find the pair that fits your every mood.