27 Fallwinter 2019 Boot Guide You’ll Want to Wear on Repeat

27 Fallwinter 2019 Boot Guide You’ll Want to Wear on Repeat

Boot season is basically the best season, and if your closet is anything like mine, it’s time for an upgrade. This is your rundown of 27 fall/winter 2019 boot styles that actually earn their spot in your daily rotation — not the ones that look cute on a hanger and then never leave the closet.

The Classic Knee-High Riding Boot

This one’s a closet staple for a reason. Pair it with skinny jeans tucked in or a midi skirt for an outfit that works for the office or brunch. Look for a slightly stacked heel so you can actually walk around all day. Brands like Nordstrom and Steve Madden have solid mid-range options if you’re not ready to splurge.

Chunky Lug Sole Combat Boots

These have taken over Instagram for good reason — they’re comfortable, edgy, and go with basically everything from flare jeans to slip dresses. Wear them with a chunky knit sweater and straight-leg jeans for that off-duty model vibe. Dr. Martens is the obvious splurge pick, but ASOS has plenty of dupes.

Suede Ankle Boots in Camel

Camel suede is one of those colors that instantly makes an outfit look more expensive than it was. Wear these with wide-leg trousers or a wrap dress for a look that feels polished without trying too hard. They’re the kind of boot that transitions from work to dinner without a second thought.

Over-the-Knee Stiletto Boots

For a going-out look that feels a little dramatic in the best way, these are it. Style them with a bodycon dress or an oversized blazer worn as a dress. This is a splurge-worthy piece, so look for a stretchy shaft that actually fits your calf comfortably.

Western-Inspired Ankle Boots

The western trend isn’t going anywhere this season, and these boots are proof. Pair them with a denim mini skirt and a graphic tee, or dress them up with a slip dress and leather jacket. Free People has some gorgeous options if you want the embroidered detailing without looking costume-y.

Sherpa-Lined Snow Boots

Function meets fashion here, and honestly, that’s underrated. These are perfect for actual winter weather when you need something warm that still looks put together. Wear with leggings, an oversized hoodie, and a beanie for the ultimate cozy errand-running outfit.

Patent Leather Chelsea Boots

Chelsea boots are endlessly versatile, but the patent finish adds a little shine that makes them feel a bit more special. These look great with straight-leg jeans and a turtleneck, or under wide-leg trousers for a work-appropriate look. Zara usually has a great budget-friendly version each season.

Fringe Detail Boots

Fringe boots bring a boho energy that pairs beautifully with earth tones and flowy silhouettes. Try them with a midi skirt in rust or forest green and a chunky knit. These are fun for fall festivals or a casual weekend outfit that still feels intentional.

Platform Combat Boots

A little extra height without sacrificing comfort — that’s the platform combat boot in a nutshell. These look great with biker shorts and an oversized hoodie for a sporty street style moment, or with a slip dress for contrast. This is a trend that skews younger but honestly works on anyone who wants a bit of edge.

White Leather Combat Boots

White boots feel unexpected in the best way once the weather turns cold. They’re a great contrast against dark denim, plaid, or all-black outfits. Keep them clean with a leather protectant spray, because trust me, you’ll want to wear these constantly.

Metallic Ankle Boots

Silver or gold metallic boots are a surprisingly easy way to add some shine to a neutral outfit without feeling over the top. Wear with straight-leg jeans and a simple sweater and let the boots do the talking. These are great for holiday parties too.

Croc-Embossed Boots

Animal print isn’t just for leopard this season — croc texture is having a real moment. A pair of croc-embossed ankle boots adds instant texture to an otherwise simple outfit like jeans and a turtleneck. Mid-range brands like Steve Madden do this trend well without the designer price tag.

Lace-Up Combat Boots

There’s something a little rebellious about a proper lace-up boot, and I’m here for it. These pair beautifully with flannel, plaid mini skirts, or oversized flannels tied at the waist. They’re sturdy enough for actual cold weather too, which is always a plus.

Pointed-Toe Ankle Booties

For when you want something a little more refined, pointed-toe booties elongate the leg and look great with cropped wide-leg trousers. These are an easy transition piece from fall into winter and work well for office dressing. Look for a block heel if all-day comfort matters to you.

Faux Fur Trim Boots

Faux fur detailing at the ankle or shaft adds instant coziness and a bit of glam. These look amazing with a camel coat and skinny jeans, or with a slip dress for a night out. It’s a small detail that makes a huge difference in how “finished” an outfit feels.

Cowboy Boots in Burgundy

Burgundy cowboy boots are a color statement that still somehow reads as neutral once you start wearing them. Try them with a denim jacket and mini skirt, or tucked-in jeans with a turtleneck. This is one of those pieces that feels a little bold at first and then becomes your favorite thing in the closet.

Quilted Puffer Boots

These snow-ready boots look like a puffer jacket for your feet, and honestly, they’re genius for genuinely cold climates. Pair with leggings and an oversized coat for a look that’s all about staying warm without sacrificing style. They come in fun colors too, like cobalt blue and hot pink, if you want to have a little fun with it.

Studded Combat Boots

A bit of hardware goes a long way in toughening up a soft outfit. Wear studded combat boots with a floral dress for an unexpected contrast, or with straight-leg jeans and a leather jacket for a full moto moment. These tend to run a little heavier, so break them in before a big day of walking.

Snake Print Ankle Boots

Snake print is the animal print pick for anyone who wants something a little more subtle than leopard. These work beautifully with neutral tones like camel or forest green, letting the texture be the statement. Try them with a simple sweater dress for an outfit that photographs really well.

Waterproof Rain Boots (Chelsea Style)

Not every boot on this list needs to be about going out — sometimes you just need something practical that still looks good. A waterproof Chelsea-style rain boot in a matte black finish works with jeans, leggings, or even a raincoat on your worst weather days. Function first, but make it fashion.

Velvet Ankle Boots

Velvet feels inherently a little festive, which makes these great for the holiday season specifically. Pair with a slip dress or wide-leg trousers for parties, or with jeans for a more casual take on the texture trend. Jewel tones like forest green or burgundy look especially rich in velvet.

Buckle Detail Moto Boots

Extra buckles and hardware make these feel a little more directional than your average ankle boot. They’re great with flare jeans and a turtleneck, giving you a 70s-meets-90s kind of energy. This is a look I keep coming back to because it never feels dated.

Two-Tone Ankle Boots

A boot that mixes two textures or colors, like suede and leather, adds a subtle design element without being loud. These work well with monochrome outfits since the boot itself carries visual interest. Try them with an all-camel or all-black look for something that feels curated.

Espadrille-Sole Ankle Boots

For the days that feel like they can’t decide between fall and summer, this hybrid boot is the answer. The espadrille sole feels a little more relaxed, making these great with wide-leg jeans or a casual midi dress. They’re an easy one for warmer fall climates.

Glitter or Metallic Statement Boots

If you’re someone who likes to have fun with getting dressed, a pair of glitter or high-shine metallic boots is basically a party in shoe form. Wear with a simple black dress and let them be the whole outfit. These are definitely more of a special-occasion pick, but worth the splurge if you love a statement.

Faux Leather Knee-High Boots

A budget-friendly alternative to the classic riding boot, faux leather versions have come a long way and look surprisingly convincing. Style with a sweater dress or skinny jeans for an easy, put-together fall look. Amazon and H&M both have great options if you’re shopping on a budget.

Block Heel Lace-Up Booties

Combining the practicality of a lace-up with the stability of a block heel, these are a genuinely comfortable option for anyone who’s on their feet a lot. They look great with straight-leg jeans and a chunky knit, or a corset top for something a little dressier. This is the boot I’d recommend to a friend who says she “can’t wear heels” — because these barely count as one.

At the end of the day, the best boot is the one you’ll actually reach for on a random Tuesday, not just the one that looked great in a photo. Mix a few of these styles into your rotation and you’ll probably find yourself wearing them on repeat all season — which, honestly, is the whole point.