Of all the cold-weather fashion choices to make, finding the perfect pair of boots ranks high on the list. Maybe even #1 since this footwear staple has a lot of heavy lifting to do. So make a smart choice. That way, your boots can go from the office to drinks to weekend outings or… well… you get the idea. In other words, boots are the bread ‘n butter of a wardrobe that’ll get you through the chilly season looking and feeling good.

A great way to know which pair is best for you is to simply look at what you always reach for when shopping or getting dressed. Do you go for the tried-n-true pieces with less detail? Or prefer a wild mix of color and pattern? Are you more likely to kick it up in jeans or sashay through the day in a skirt? Not sure? Just pause for a moment and check out what’s piled up on that chair in your bedroom (we all have one) at the end of the week.

With that in mind, here’s a guide to help you find a pair of boots that not only complement your style, but that you may never want to stop wearing.

Style:

Classic Minimalist

Best Boot:

Wilder

Why:

This modern and slightly feminine take on the Chelsea boot is for you if you live in classic combos with clean lines. Like a crewneck sweater and wide-leg trouser, or a blazer paired with the perfect midi shirtdress. The boot’s low heel is just the right height for a swift stride, and a balance to the full-grain leather that is ever elegant.

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Style:

Luxe Bohemian

Best Boot:

Starr

Why:

If you can’t get enough of the vivid shapes, colors and patterns inspired by the 70s, the Starr is the way to go. Whether you can’t resist the cognac color in hand-finished leather or swoon over the soft taupe suede, either style works beautifully with a quintessential floral midi dress and vivid maxi coat for your next rock concert.

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Style:

Downtown Chic

Best Boot:

Parker

Why:

If your fashion crushes typically entail an off-duty model, then there’s no doubt you'll fall for the Parker. Its classic-yet-edgy Chelsea silhouette marries well with everything from leather jackets to skinny jeans. Slip into this boot, which sports a breathable leather interior, and conquer the day, or your crush in style.

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Style:

Mix-n-Match Maven

Best Boot:

Victoria

Why:

When you've perfected toggling between trend-forward pieces and classic staples, you've got to give the Victoria a go. It's this season's take on the classic hiking boot with sleek details like gore tabs and full-grain leather that make for an unexpectedly cool and versatile look. As a matter of fact, Victoria has been seen roaming around with everything from jeans to midi skirts and the occasional evening dress.

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Style:

Polished Preppy

Best Boot:

Spencer

Why:

For a more uptown taste, the Spencer is probably your cuppa (tea). With a nod to equestrian styling and an over-the-knee silhouette, it’s a long, lean boot that let’s you hit your stride, and jump a puddle or two. Even better, it polishes up a button-down shirt and pair of skinnies, or plays perfectly with a mini dress.

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Now that you’ve gotten the lowdown on the season’s five coolest boots of-the-moment, it’s time to select your style. The best part? It doesn’t have to be just one. Maybe more than one mixes with your personal style? Or maybe we’ve inspired you? So try out more than just one. Happy shopping!