Over the weekend Tonya made a compelling case for kitten heels, and I went into Labor Day weekend sales with shoes on my mind. Another style also caught my attention: a sleek pair of knee high boots. There are few wardrobe purchases I love more than a great pair of boots. The right boots can completely change an outfit—and, perhaps more importantly, they can make the rest of your wardrobe work harder. But here’s the thing: the best boots for you aren’t necessarily the boots that are trending this season.

A pair of knee-high riding boots might be perfect for one woman’s wardrobe and completely impractical for another. Someone else might get far more wear out of a sleek ankle boot, while a fashion girl with a more eclectic wardrobe may want something with a little more personality.

Instead of asking, “What boots are in style?” I think the better question is:

“What kind of boots actually make sense for my personal style?”

Your shoes should support the way you already dress—not force you into a completely different aesthetic. Here are some of the most common personal style personalities and the boots that tend to work best for each one (click the photos to shop).

If Your Style Is Classic

If your wardrobe is filled with tailored trousers, button-down shirts, cashmere sweaters, straight-leg denim, wool coats, and timeless handbags, you probably don’t need an overly complicated boot collection. Your best investment is a classic leather ankle boot or knee-high boot with a simple silhouette.

Look for:

• Minimal hardware
• A low or medium heel
• Smooth leather or refined suede
• Neutral colors like dark brown, cognac, black, or deep burgundy

A classic knee-high boot is very versatile because it works beautifully with dresses and skirts while also looking polished with tucked-in denim. The key is to avoid details that will make the boots feel dated quickly. Your style is already doing the work.

If Your Style Is Classic With a Twist

Maybe your wardrobe is mostly timeless, but you like adding one unexpected element to your outfits. You wear classic trousers with a slightly oversized sweater, a feminine dress with loafers, or a traditional coat with something a little edgier.

For you, the ideal boot is classic in shape but has one interesting detail.

Think:

• A slightly square toe
• Sculptural heels
• Dark brown suede
• A riding boot with a subtle equestrian detail
• A Western-inspired boot that isn’t overly cowboy
• A sleek Chelsea boot

You want the overall silhouette to feel timeless, but you don’t necessarily want the most basic version available.

If Your Style Is Feminine

If you gravitate toward dresses, skirts, pretty blouses, delicate knits, and softer silhouettes, boots can be a wonderful way to keep your outfits from becoming overly sweet. Look for boots that have a sleek, elongated silhouette instead of something extremely chunky.

Knee-high boots are especially beautiful with feminine clothing. Try them with:

• Midi dresses
• Floral skirts
• Slip dresses
• Sweater dresses
• Pleated skirts
• A-line skirts

Suede is another excellent choice for this style personality because it has a softer appearance than polished leather. Brown, taupe, chocolate, and warm cognac can all look gorgeous with a feminine wardrobe.

If Your Style Is Minimalist

Minimalists should resist the temptation to collect every boot trend that comes along. You probably need fewer boots, but better ones. Look for clean lines and uncomplicated shapes. A beautiful black, dark brown, or espresso ankle boot can potentially work with the majority of your wardrobe.

If you prefer a more modern look, consider:

• Square-toe ankle boots
• Sleek Chelsea boots
• Minimalist knee-high boots
• Architectural low heels
• Streamlined riding boots

Avoid excessive buckles, studs, logos, and decorative details. Your ideal boot should almost disappear into the outfit.

If Your Style Is Bohemian

If you love flowing dresses, relaxed denim, suede, crochet, fringe, natural textures, and an effortlessly undone aesthetic, you have a little more freedom when it comes to boots.

This is one of the style personalities where suede really shines.

Try:

• Western boots
• Slouchy ankle boots
• Suede knee-high boots
• Chelsea boots
• Vintage-inspired leather boots

Brown, tan, cognac, and distressed leather tend to complement this aesthetic very well. Just remember that bohemian doesn’t have to mean heavily decorated. A simple suede boot can actually look more sophisticated than one covered in fringe and embellishment.

If Your Style Is Edgy

If your wardrobe includes leather jackets, denim, mini skirts, oversized silhouettes, graphic pieces, or a healthy dose of black, your boots can absolutely have some attitude.

This is where you can experiment with:

• Lug soles
• Combat boots
• Moto boots
• Platform boots
• Chunkier Chelsea boots
• Pointed-toe ankle boots

The trick is to make sure the boots complement your wardrobe rather than becoming a costume. If you wear a lot of edgy pieces already, you may not need the most extreme boot available. Sometimes a slightly chunky Chelsea boot is enough to give a classic outfit the edge you’re looking for.

If Your Style Is Preppy

If you love cable-knit sweaters, pleated skirts, button-downs, loafers, cardigans, and classic outerwear, your boots should feel similarly polished. Think equestrian-inspired and traditionally tailored.

Great options include:

• Riding boots
• Sleek knee-high boots
• Chelsea boots
• Penny-loafer-inspired boots
• Simple leather ankle boots

Brown leather is especially beautiful with a preppy wardrobe, particularly when paired with navy, cream, camel, burgundy, and denim.

If Your Style Is Relaxed and Casual

If your everyday wardrobe is primarily jeans, sweaters, leggings, casual jackets, sneakers, and easy dresses, don’t buy boots that require you to dress up every time you wear them. Instead, look for boots that can handle real life.

A Chelsea boot, Western-inspired ankle boot, or simple flat knee-high boot can work beautifully with casual clothing. The most important thing is comfort. If you have to talk yourself into wearing your boots because they pinch, are difficult to walk in, or don’t work with your lifestyle, they’re not a good wardrobe investment no matter how beautiful they are.

If Your Style Is Trendy

If you love experimenting with fashion, boots are one of the easiest places to have fun.

You might enjoy:

• Metallic boots
• Colored suede
• Slouchy boots
• Western boots
• Platform boots
• Unexpected heel shapes
• Statement knee-highs

But there’s one rule I’d recommend: Keep your trend boot from becoming your only boot.

A wardrobe works best when you have a foundation of timeless pieces and then sprinkle in trends. For example, you might own one beautiful brown leather ankle boot that you wear constantly—and then add a burgundy suede knee high boot because it’s fun.

The Most Important Boot Rule

Before buying a pair of boots, look at your actual wardrobe, not your Pinterest board or saved Instagram posts.

Ask yourself: What outfits would I actually wear these with?

If you can immediately picture at least a handful of outfits, that’s a very good sign. If you’re struggling to think of even two, the boots may be beautiful—but they’re probably not a good investment for you. Personal style isn’t about owning every beautiful thing. It’s about knowing what belongs in your wardrobe. And the perfect pair of boots should feel like they were made for the woman you’re already dressing.

Which boot styles are you most drawn to? Let us know in the comments.

Xo, Courtney