If you’re a real shoe fanatic, it can be hard to resist a great pair. However, shopping strategically is the best goal to get more bang for your buck and to max out the versatility of your wardrobe. Of course, you can’t just stop at two or three pairs. That’s perfectly fine—no one’s asking you to. However, if you want to select some great pears that you can mix and match with your other great fashion finds, there’s a few basic styles that you should focus on acquiring.

Ankle Boots: They Go With Everything

It’s no exaggeration to say that ankle boots work well with nearly any outfit in any season. From skinny jeans to dress trousers to dresses, these small wonders are available in almost every color, material and heel height you can imagine. For an amped up look for a night on the town, try a pair with your little black dress. And for a smart casual Friday look at the office, wear them with some dark blue or black classic wash skinny jeans and a blazer with your favorite blouse.

Chelsea Boots: Sophisticated and Modern

This footwear has a distinctly rocker vibe, worn by notables like Jim Morrison, Nico of the Velvet Underground and the Beatles. These days, the iconic boot is now sported by celebs such as Kendall Jenner, Julia Roberts and Kanye West. Most versions have a low heel, so they’re incredibly comfortable for days when you’re running around town. And while the black leather ones were once ubiquitous among hip trendsetters, modern varieties also come in suede and in a wide array of hues. Try them with black skinny jeans or dark-colored cigarette pants, or pair them with a shorter A-line or shift dress for a cool, retro vibe.

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Striking Stilettos for Dressier Occasions

There’s nothing like a pair of stilettos to lengthen your leg and boost your height. Opt for versions that end at or above the ankle for a cosmopolitan addition to any upscale, dressy ensemble. And while basic black serves as a great go-to item, tones such as wine, cognac, oxblood and burgundy also provide pizzazz.

Moto Boots Make an Impact

Moto boots have been around for decades as paragons of comfort and style. Some sport straps and buckles across the shaft while others are the lace-up, chunky-sole types sported by punk and post-punk musical pioneers in the ‘70s, ‘80s and 90’s. They’re a great alternative to flats when you’re out and about, serving up decidedly more edge in your look. Pair with feminine touches such as floral prints or lace, or go full-on underground with your street style by wearing them with black skinny jeans, a graphic tee and a leather jacket.

boot style guide

Tall Boots Hit a High Sartorial Note

No boot guide would be complete without a mention of the tall boot, a timeless classic that should be in anyone’s wardrobe. And whether you choose flat versions or ones with a bit of a heel, you’ll get plenty of wear out of them in the colder months. Pair them with skinny jeans to bump up your daytime looks. Alternatively, you might include them with a simple A-line frock, some opaque tights and a few accessories for a put-together yet somewhat casual nine-to-five ensemble. For everyday wear, opt for the calf-height or below-the-knee versions. However, while over-the-knee and thigh-high varieties take some courage to pull off, they can work in some settings—just keep the amount of skin shown between the top of their shafts and your skirt or dress hemline to under five inches, and try topping your outfit with a coat for some effortless sophistication.

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Amp Up Your Style With the Right Kind of Boots

With so many versions, materials and colors, you have a lot of reasons to include a wide range of boots in your closet. The decision of which kinds to add to your outfit is just a matter of the look that you wish to achieve. Some reward you with a little extra elegance, while others provide a tougher edge that brings your ensemble up to the next level. Still others are perfect in casual, work or nighttime settings. If you only buy a range of basics to add to your closet, this will still be one of the best fashion investments you can make.

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