Winter in New York City may look like a whimsical wonderland during holiday TV specials, but IRL, it sucks — especially for our shoes. Ballet flats and strappy heels can’t survive the sludgy snowstorms that cover the city’s sidewalks, which is why a cozy (and let’s be real, actually practical) switch-up to your footwear is essential to surviving those zero-chill days.
Like florals and spring, boots and winter go hand-in-hand. But with so much on the market, the best way to start is to hone in on the classics. Consider this your no-fail guide to the boots your closet should definitely have.
A favorite of every Kardashian-Jenner out there, the thigh-high has made a remarkable comeback in recent years. Blame it on lampshading, but somehow the thigh-high + an oversized sweatshirt = 2018’s most recognizable celebrity outfit formula.
These are the Chanel quilted bag of thigh-high boots: a classic that can never be beat.
Looking for something with a little more attitude? We got you.
The Rider Boot
The motto here: comfort, but make it fashion. Once a staple reserved for skilled equestrians, these casual options tie any low-key Sunday morning outfit together.
These boots embody everything you’ve known and loved about rider boots: a barely-there heel, a knee length, and a rustic vibe.
For an edgier, grunge-inspired take, slip into this buckle-embossed pick.
The Chelsea Boot
Legend has it that Queen Victoria of England requested a riding boot that was easy to slip on and off without any laces, which is how the Chelsea boot came into existence.
These can handle the toughest of snow storms. Trust us.
For a more modern play on the timeless style, why not try a millennial pink pair?
The Snow Boot
This one is less optional, more of an essential. Sure, the “duck boot,” which has rubber soles and a leather upper, may not be the cutest, but when you’re trekking through inches of snow, your dry feet will thank you.
When a snow day turns into a snow week, step into these all-business boots. Not a single flake will get through these waterproof, faux-fur-trimmed shoes.
Heel addicts, rejoice! These platform boots will give you all of the height, without leaving your feet in the cold.
The UGG Boot
Ah, the UGG boot. Though we have a love-hate relationship with the divisive footwear style, we’ll go ahead and say it: They’re pretty damn comfortable.
Chances are, you already have these in your closet. But, they may have suffered from last year’s intense winter, so why not grab another pair (or three)?
These sweet and playful alternatives to the taller UGG boot will always be everyone’s guilty (or not-so-guilty) pleasure.
If you want to give these classics a modern refresh, then you’ve come to the right place. Take a look at some of our favorite boots of the season, below.
This ankle boot may be tiny, but it’s mighty in style. The neutral-toned color-block gives a nod to summer’s favorite pattern, but still stays on the winter aesthetic. It’s short, sweet, and to the point — just how casual style should be.
Match your favorite burgundy sweater with these deep-red ankle boots. The foldover and back tie create a feminine feel to contrast the dark tone, and the block heel will let you strut in style while staying comfortable.
Who said florals are reserved for spring? You can easily tie in this botanical design with any of your winter ensembles with these booties. They’re dark and romantic, and embody a dreamy Victorian aesthetic.
For a sky-high style with an Americana vibe, strap on these boots. They hit just under the knee, and have a full five layers of tiered tan fringe for some lively movement to any of your winter outfits.
These boots give the average ankle bootie a run for their money. These pointed-toe boots are embellished with a rainbow of jewel-toned crystals, which pop in contrast to the sleek black suede base.
Snakeskin patterns are highly underutilized, and it’s about time it made a comeback. And what better way to wear this primitive print than through a statement pair of block-heeled booties? These vibrant snakeskin-print boots are great for amping up any basic outfit.
The sock boot is one of the most popular styles of this year. But if you’re trying to save up for holiday shopping, you might have to opt out on the classic Balenciaga boot. These budget-friendly alternatives from Splendid are just as sleek and sexy.
If you’re into a more subtle style, then reach for the classic black ankle boot. This pair from Louboutin embody the same polished, red-bottomed style as their stiletto counterparts, but are undeniably more comfortable.
These royal blue boots are fit for a queen, and your shopping bag. They hit right at the knee, and the adjustable straps allows you to make your fit as snug or loose as you please. The small tapered heel gives you just enough lift without becoming a hazard to your ankles.
So the signature UGG boot is a classic, but the clunky tall boots do need a makeover. That’s why we’re reaching for these shorter, tailored alternatives. The buttoned side allows you to customize your fleecy-lined boots to your OOTD.
These booties give a slight nod to another footwear classic: the loafer. It has a similar vintage-inspired leather finish, and dons a small silver buckle for a simple, classy touch. They’re perfect for topping off any workwear attire.
Nothing beats a classic, which is why we love these knee-high boots. They’re everything you could ever ask for in a pair of boots: a thick heel for endless wandering, a comfortable leather material, and a warm black hue to work with any outfit of your choosing.
I live for a good cheetah moment, and these Sam Edelman booties are definitely impressive. The small kitten heel is given life with the vibrant animal print, and the elongated pointed toe adds a contemporary style to a classic look.
If you need a break from heels, then slip into these Western-inspired booties. They have a tolerable barely-there stacked heel, but still stay bold through the eye-catching cedar hue. The elastic sides let you slip in and out of these boot with ease, so you’ll have all the style without sacrificing comfort.
When the rain just won’t seem to go away, it’s time to break out the rain boots. But, instead of sticking to clunkier, heavyweight rain boots, try on this itty-bitty number instead. They’re small, sleek, and still have a Chelsea boot vibe that won’t water down your wardrobe.