How to Choose Ankle Boots That Work With Everything

A good pair of ankle boots carries you from early fall to spring. The right pair depends on how much you walk, what you wear on your legs and the weather where you live.
Common styles
| Best for | Watch for | |
|---|---|---|
| Chelsea boot | Everyday wear, pulling on fast | Elastic that loosens over time |
| Block-heel bootie | Work and evenings, stable height | Heels over 3 in. get tiring |
| Lace-up boot | Walking, adjustable fit | Takes longer to put on |
| Stiletto bootie | Dressy outfits | Uneven ground and long days |
Match the boot to your outfits
- Skinny or straight jeans: almost any ankle boot. Cuff or tuck if the hem bunches.
- Wide-leg trousers: a heeled bootie the hem can fall over.
- Dresses and skirts: slim boots that sit close to the ankle look neatest.
Material
- Leather molds to your foot and lasts longest, at a higher price.
- Faux leather wipes clean and handles rain, but does not stretch.
- Suede and faux suede look soft and casual but mark with water unless sprayed.
Picks to look at

Perforated cutout ankle bootiesAnkle booties with perforated sides, V cutouts and a low stacked heel, in black, taupe, grey and tan.
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Platform heels with ankle strapFaux suede platform pumps with a chunky high heel and a buckled ankle strap that keeps the foot in place.
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Side-zip ankle bootiesClassic ankle booties with a side zip, a pull tab and a low stacked heel for everyday wear.
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Ballet flats with a knot bowSoft ballet flats with a knotted bow, a flexible sole that folds and a grippy rubber tread.
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