Shopping·11 min read

Our Favorite Boots Worth Investing In

investment-boots-header
Design: theSkimm | Photos: Reformation, Free People
October 21, 2024

Products you buy through our links may earn us a commission. Oh, and if something's out of stock, oops, it was there (and all prices were accurate) at time of publication.

If you're like us, you could fill an entire closet with just boots. So, from a price-per-wear perspective, it just makes sense to invest in a few pairs. (It's science.) Ahead, we’ve found high-quality styles you'll wear season after season — from riding boots to heeled knee-high boots for special occasions — so you can buy fewer pairs over the years, and love the ones you’re with longer. These boots are built to last.

riding-boot
Everlane

A riding boot to grab before it’s gone…

This boot is made out of glossy black or brown leather and has that timeless curved shaft and square toe you’d expect of an investment-worthy riding boot. They have a padded insole, so they’ll be comfortable for stomping around in all day. We’re predicting these will sell out by the end of the season, so don’t wait. ($398, Everlane)

Buy it
pull-on-boot
Free People

A pull-on boot that looks vintage…

If you’re not ready to shell out for the Frye Campus Boots, try this similar style. They have a wearable stacked heel, and they’re pre-distressed to look as if you’ve been wearing them for years. They’re wide enough to tuck jeans into, but also look great with dresses. ($268, Free People)

Buy it
wide-calf-boot
Free People

A wide-calf option by a trusted brand…

We’ve been wearing Sam Edelman boots for as long as we can remember, and they’ve never let us down, comfort-wise. These knee-highs have a block heel that’s easy to walk in but slim enough to make them chic. They have an inner zipper for easy on-and-off, and come in gorgeous colors like deep red and tan. They also come in a regular-calf version. ($200+, Free People)

Buy it
patent-boot
Shopbop

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 wearing them, they never squish our toes. They also come in a knee-high style we’re currently coveting. ($395, Shopbop)

Buy it
mini-uggs
Anthropologie

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

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, Anthropologie)

Buy it
moto-boots
Nordstrom

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 a harness strap on the side. Take it from us, they’re incredibly comfortable, and we love to pair them with everything. We’ve even worn them with leggings to take our athleisure to the next level. ($295, Nordstrom)

Buy it
western-ankle-boot
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. They come in 11 colors, and customers rave about how comfortable they are. ($298, Free People)

Buy it
moto-bootie
Frye

A 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. ($189.98+, Frye)

Buy it
weatherproof-bootie
Neiman Marcus

A black bootie made for city living…

This brand is from Montreal, so you know they’ll be equipped to handle all weather. They’re downright sleek, and are insulated on the inside. The chunky rubber sole will keep you from slipping around even if it’s raining or snowing. ($525, Neiman Marcus)

Buy it
heeled-bootie
Nordstrom

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 made by the brand that makes the most comfortable loafers, so you know you’ll be able to walk miles in these. ($200, Nordstrom)

Buy it
going-out-boot
Nordstrom

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

Each detail is better than the last, from the pointed toe to the skinny heel to the Western-inspired shaft. 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 snakeskin version to really make a statement. ($258, Nordstrom)

Buy it
doc-martens
Amazon

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 fashion 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. ($209.95, Amazon)

$209.95 at Amazon
ankle-boot
Shopbop

An ankle boot that spans seasons seamlessly…

If you’re not a traditional round-toe fan, may we suggest this slightly square-toed bootie? These are just about perfect, and are handmade out of the glossiest, smoothest Italian leather we’d love to get our hands on. Plus, the deep chocolate color is so pretty. ($545, Shopbop)

Buy it
cowboy-boot
Tecovas

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 come in so many colors that it’ll be easy to find one that matches your style. They only look better and get more comfortable as you wear them. ($345, Tecovas)

Buy it
bean-boot
L.L.Bean

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

We recommend these for cold, rainy days. They’ll keep your feet dry and warm, since they’re shearling-lined,  so if you need something reliable for your commute and trekking through sidewalk puddles, these are an ideal choice. Be sure to check out L.L.Bean’s sizing guide — they suggest sizing down instead of up. ($289, L.L.Bean)

Buy it
weather-chelsea-boots
Free People

Waterproof boots that don’t skimp on style…

If you’re looking for 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’ll actually protect your feet and keep them warm. Plus, the rubber bottom will prevent you from slipping. Each colorway is cuter than the last. ($130, Free People)

Buy it
heeled-boot
Revolve

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. The “Vanilla” color would look great with a winter white ensemble. ($360, Revolve)

Buy it
heeled-knee-high
Reformation

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

You’ll have legs for days in these sleek, knee-high boots. The leather upper is buttery soft, and they’re practically begging to be paired with a fall dress. Go classic with the black, or get the brown croc. Life’s short, wear the fun boots. ($448, Reformation)

Buy it

Live Smarter

Sign up for the Daily Skimm email newsletter. Delivered to your inbox every morning and prepares you for your day in minutes.