The Best Boots of Fall

  • Boots are an autumn must: They go from day to night, work to weekend, and through just about every type of weather. And, because they’re pricey compared to shoes, they’re an investment. It’s a big commitment! To make your life easier, here’s my guide to why these 5 fall boot styles are right for you.

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  • 1. Stacked-Heel Booties
  • Comfortable and classic, a short bootie with a stacked heel is the season’s most versatile style. Look for a shaft that hits above the ankle, a rich suede for a casual feel and a wooden heel for optimum comfort.
  • Why we love them… A stacked heel gives you height that you can walk in, great for weekends!
  • How to wear them… Under a pair of flare jeans (instant leg lengthening!), with skinnies or over black tights with a sweater dress or skirt.
  • Hipstr, in Taupe Suede, $99.95; stevemadden.com.
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  • 2. Over-the-Knee Boots
  • Looking to add some DRAMA to your wardrobe? An over-the-knee boot is the answer.
  • Why we love them… A sleek stocking-style boot can elongate your legs (if you’re petite; be sure to go monochromatic to avoid cutting the leg line).
  • How to wear them… Over a pair of black skinny pants with a tunic-style top or tights with a dress for maximum lengthening.
  • Bove in Black Suede, $200; aldoshoes.com.

MORE: 3 Style “Risks” Worth Taking

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  • 3. Moto Boots
  • These rough-soled black boots make you feel biker chic without the risk of actually riding on the back of a Harley.
  • Why we love them… Instant cool girl cred plus comfortable walking shoes at the same time.
  • How to wear them... Over skinny jeans of any hue or paired with a flowy dress and tights for a 90s-grunge contrast.
  • INC Blayre Booties, $139.50; macys.com.
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  • 4. Skinny, Pointy Booties
  • The quintessential work-to-drinks boot is chic in a slim or block heel.
  • Why we love them... Because they go from work to evening to weekend; a sturdy but chic alternative to your go-to black pumps!
  • How to wear them… For work, they pair just as well with trousers and skinnies as they do with dresses and skirts; try them with waxed jeans for the weekend.
  • Pirhana Dress Booties, $129; ninewest.com.
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  • 5. Two-Tone Chelsea Boots
  • A Chelsea boot never goes out of style—this season find it in unexpected hues and varying heel heights.
  • Why we love them… Two-tone makes a statement on its own and gives an instant style upgrade—so the rest of your outfit can be plain-Jane and you still look cool.
  • How to wear them… With casual skinny jeans or leggings, or under a flare.
  • Leather Block Heel Ankle Boots, $99.90; zara.com.
The Best Boots of Fall
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