30+ Fall Boots that Will Last More Than One Season


It’s finally cool enough in most places to begin pulling out some of the best cold-weather wardrobe staples: boots and booties. October is the ideal time to pick up a new pair, since boot-wearing season has only just begun! A great pair of high-quality suede or leather boots tend to hold up best over time, so I find that they’re worth the investment.

Rather than follow the fall boot trends, I try to gravitate towards classic silhouettes that will stand the test of time in neutral shades like brown, black, beige, and gray.

Below, I’m sharing the best boots for fall, including everything from chelsea boots to knee high boots and over-the-knee boots. You’ll also find my recommendations and tips for styling boots in the notes at the bottom of the post.

Outfit Details: Cuyana Sweater (similar, less expensive here), Frame Jeans (part of the Fall 2020 Capsule Wardrobe), Loeffler Randall Boots (under $200 lookalike here)

Chelsea Boots

When you’re planning on taking a fall trip, walking around a city, or being active all day, there’s no better fall shoe than a comfortable pair of chelsea boots that you can quickly slip-on. While chunky combat boots with lug soles are trending right now, like Dr. Martens, I like a simpler, low-heel boot that will look just as great today as it will in ten years. Here are some of the best fall chelsea boots at different price points. (PS—If you happen to like the look of combat boots, look for styles with a classic twist, like these lace-up boots in pure black or suede.)

Ankle Boots

There’s something so classic about simple suede and leather ankle booties. Most of mine have block heels for added stability, and I while I prefer almond- or round-toe styles, pointed- or square-toe booties can have a classic look as well. As far as colors go, most of the pairs of boots in my closet are smooth suede or leather ankle boots in a neutral color. However, the right pair of snakeskin or textured boots, like this black leather croc option, can go a long way in adding interest to an otherwise “flat” outfit.

Knee-High Boots

When I want a lift, I prefer chunky heeled boots over stilettos, since they’re more versatile and laid back. I also like heeled boots better than riding boots for daily wear. These collectible tall boots by Loeffler Randall are the perfect heel height and color to pair with fall dresses in all lengths, and they also work with skinny jeans. Sam Edelman, Tory Burch, Vince Camuto also make gorgeous knee-high styles. I linked favorites from Asos, Nordstrom.com, and more below.

Over-the-Knee Boots

Flat over-the-knee boots are a fall fashion staple because they are so easy to wear. I bought this pair from Nordstrom several seasons ago and still reach for them when I want to look styled in a dress or skirt without added height. Stuart Weitzman is best known for its classic over-the-knee styles. Marc Fisher, Steve Madden, Topshop, and even Zara make comparable styles for much friendlier price points. I love this pair from Zappos, and I found this one on Amazon Prime recently.

What Do I Wear with Each Fall Boot Type?

Pulling out leather and suede boots and booties year after year is one of the best parts of fall. The right pair can become the defining detail of your fall looks, bringing them from cute to absolutely timeless!

Styling the best fall boots should usually begin with what you plan on wearing. Here are a few outfit ideas and the pair of boots I recommend adding.

  • For pants, try short booties. These look great with skinny jeans but work just as well with wide-leg cropped pants. See one way I commonly style mine here and here.
  • Opt for leather chelsea boots for fall trips. They’re great if you want something that’s polished yet comfortable enough to walk around in all day.
  • Pair pants and short booties in similar colors for a monochromatic, elegant look. I like black boots with charcoal skinny jeans and a white sweater.
  • Reach for knee high and over-the-knee styles when you’re wearing midi or maxi dresses or skirts. See examples here and here. Tall boots will double as an extra layer on chilly days.
  • For mini-length hems, wear knee high or over-the-knee styles with bare legs early in the season. You can add black tights to warm up as the weather cools down.

Hopefully this post brought you an assortment of boots in rich, warm shades to add a classic look to your fall outfits! There’s hardly ever a need to invest in ultra-luxe styles like Gucci or Saint Laurent; many high-quality fall boots can be purchased for less than $250, even $100.

PS—I also recommend a solid pair of flat loafers, winter boots/hiking boots, rain boots, and Ugg slippers for fall. I’ll share more fall shoes in these styles later in the season. xo!

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