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.

  • 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;
  • 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;

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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;
  • 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;
  • 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;
The Best Boots of Fall

This will always be my favorite picture of my mom, because it displays the sheer joy in her face as she reaches for her favorite present-- a roll of twenties. Happy Mother's Day, Terri. You really are the best! ❤️❤️❤️ (And Happy Mother's Day to anyone else reading this, if it applies. And if it doesn't, have a fabulous Sunday!)

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