Shopping·10 min read

Our Favorite Boots Worth Investing In

Design: theSkimm | Photos: Shopbop, Reformation
October 23, 2023

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If you’re like us, you could fill an entire closet with just boots. Big ones and small ones, short ones and tall ones, we simply can’t get enough. We’ve found styles sure to be your go-tos season after season — from snakeskin booties to heeled knee-high ones — so you can buy fewer pairs over the years and love the ones you’re with longer. PSA: A lot of these price tags are on the higher end, but when you splurge on the right items, you’ll get long-lasting wardrobe staples that are actually worth it. These boots are made for everyday life.


An ankle boot that instantly dresses up any outfit…

We’re huge Staud fans, and these ankle boots might just be the best shoes they’ve ever made. They have an elegant pointed toe and come in soft black leather that makes even a jeans-and-a-T-shirt outfit feel special. No matter how much we’re stomping around, they never squish our toes. They also come in a knee-high style we’re currently coveting. ($395, Shopbop)

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Saks Fifth Avenue

A classic pair of mini Uggs that will never go out of style…

We said what we said. The It Ugg of the moment may come and go, but this ultra mini pair is forever. They’re lined with the soft, warm shearling the brand is known for, and the outer is coated with a water-repellent treatment. These are the best “going to grab a coffee, heading to a Pilates class, or taking the dog for a walk” shoes, and you can’t tell us otherwise. ($150, Saks Fifth Avenue)

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A moto boot that makes a big statement…

Motorcycle boots are back in a big way, and they’re much more versatile than you might think. These have a round toe with six buckles up the side. Take it from us, they’re incredibly comfortable, and we love to pair them with everything from denim to dresses and skirts. We’ve even worn them with leggings to take our athleisure to the next level. ($189.95, Nordstrom)

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Free People

A classic ankle boot with a Western vibe…

With the squared toe and contrast stitching, these boots are giving yeehaw in the most subtle way. They span seasons and play nicely with pretty much anything, from dresses to denim to skirts. They come in 15 colors, and customers rave about how comfortable they are. ($298, Free People)

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Neiman Marcus

A short moto bootie for a bit of edge…

We can vouch for this biker gang-worthy bootie we’ve found ourselves pulling on year after year. They make us feel supremely cool and comfortable, no matter the occasion. Like all Frye boots, they last forever, and the pebbled leather only looks better with wear. The silver side buckle is a nice added touch. ($278, Neiman Marcus)

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A black bootie with a weatherproof finish…

If you’re ever faced with the decision of whether to get the Aquatalia boots or not, you get the Aquatalia boots. These are downright sleek, and are made of the brand’s signature weatherproof leather. We love the slightly chunkier sole for an updated take on a classic. ($350, Aquatalia)

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A heeled wear-everywhere black bootie…

Raise your hand if you wear your favorite heeled black booties literally into the ground. So, maybe it’s time for an upgrade? Between the flared block heel and the square toe, these have all the elements to become your new go-to. They’re like The Matrix in a shoe and are made by the brand that makes the most comfortable loafers, so you know you’ll be able to walk miles in these. ($190, Nordstrom)

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A Going Out Boot™, if we’ve ever seen one…

The pointed toe, the skinny heel, the Western-inspired shaft. Swoon. Pair these with the Skims dress everyone is obsessed with, or jeans and an oversized sweater, and you’re ready to let your boots do the talking. We love the dark chocolate colorway, but they also come in cream, black, a lighter brown, and even snakeskin. ($258, Nordstrom)

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A cult-classic boot that’ll give you a little lift…

Dr. Martens are known for their durability, and these are no exception. What makes them special is the added platform your most fashionable friend would approve of. While the leather outer is not necessarily waterproof, the signature Goodyear welt bottom is. We love stomping around in ours on bitter winter days, since they’re surprisingly warm. ($190.95+, Amazon)

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An ankle boot that spans seasons seamlessly…

If you’re not a traditional round-toe fan, may we suggest this slightly squared, pointed-toe bootie? These are just about perfect, and are handmade out of the glossiest, smoothest Italian leather we’d love to get our hands on. The price is a little steep, but boots of this quality will truly last you decades with some upkeep. ($495, Net-A-Porter)

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A cowboy boot you’ll wear for years…

These midcalf beauties have a small stacked heel, pointed toe, and ornate contrast stitching, like traditional Western boots. They have a padded upper, so when you’re mounting your horse — or more likely, showing up to work with the coffee that made you late — they’ll still be comfortable. We’re having a hard time choosing between the black or brown. ($498, Reformation)

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Cole Haan

A heeled knee-high boot with a padded insole…

These have a padded insole to make sashaying around a little softer on your knees, plus arch support so you can stay on your feet all day, whether you’re headed to the office or hitting the streets for a shopping marathon. They’re made of buttery-soft leather (just how we like it) and come in classic black. ($300, Cole Haan)

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A rounded-toe Chelsea boot…

For a true rounded toe, look no further than this Chelsea boot made out of supple Italian leather. It has a cushioned insole and stretchy sides, so getting them on won’t feel like a chore. The contrasting bottom sets them apart, and they come in black and brown. Psst…did we mention their often sold-out sock bootie is one of the most comfortable pairs of shoes we’ve ever put on our feet? Grab them too. ($195, Everlane)

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A classic L.L.Bean shearling-lined duck boot that’s great for wet weather…

We recommend these for cold, rainy days. They’ll keep your feet dry and warm, so if you need something reliable for your commute and trekking through sidewalk puddles, these are an ideal choice. Plus, we think they’re Cameron Diaz in The Holiday chic, don’t you? Be sure to check out L.L.Bean’s sizing guide too — they suggest sizing down instead of up. ($249+, L.L.Bean)

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Chelsea boots that don’t skimp on style…

If you’re seeking boots that are weatherproof, but don’t make you look like a kid on a snow day, these are the ones. They’re made by Sorel, so you can trust that they’re waterproof and will keep your toes warm on the chilliest of days. Plus, the rubber bottom will prevent you from slipping as you’re stomping around. The winter white is so chic. We also love the lace-up version with a splashy bottom. ($180, Revolve)

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A heeled boot we simply can’t resist…

This square-toe boot has a sculptural flared heel and pieced upper, which makes them feel unique. They would look just as good with a sweater dress as your favorite pair of jeans with a bodysuit. Customers say they’re even better in person, and personally, we’d love to see the “butter” colorway with our own eyes. ($360, Revolve)

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A heeled knee-high boot to show off your legs…

You’ll have legs for days in these sleek, knee-high boots that have a just-right block heel. The leather upper is buttery soft, and they’re practically begging to be paired with a fall dress or skirt. Go classic with the black, or get the patent croc or deep red. Life’s short, wear the fun boots. ($478, Reformation)

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