How to Style Boots: Choosing the Right Pair for Every Outfit

It’s officially boot season! With so many different styles of boots to choose, I’m sharing my tips for how to style boots and choosing the right pair for every outfit. The right boots can make jeans look more polished, change the mood of a dress, or give a cozy fall outfit that extra layer of style.

Of all of the different types of shoes, boots are by far my favorite to wear. I love how they add a depth to outfits that other shoes styles can’t match. While grabbing your favorite pair of boots to finish off your look is fine, I’m sharing more about why certain boots can add a timeless but modern vibe to different outfits. I’ll walk you through the styles worth having in your closet and how to wear them in ways that feel elevated and effortless.

How to Style Boots

From classic riding boots to chic ankle boots, and everything in between, styling boots comes down to pairing the right shape and height with your outfit. The key is choosing a style that complements your look and gives you the mood you are after. Let’s break it all down.

Are Boots In Style?

Boots are never really “out of style.” Trends like pointed toes, square toes, or round toes come and go, but some boot styles are timeless. Think classic ankle boots, Chelsea boots, or even knee-high boots. These are the boots you’ll wear again and again.

When I shop for boots, I look for pieces I know I’ll actually wear. I absolutely love ankle boots with straight-leg jeans, and is it really fall if I’m not wearing boots with dresses? If you worry about toe shape being in style, almond toe is the most classic and natural shape that you can’t go wrong with. Also, choosing timeless colors like black, shades of brown, or cream ensures your boots will go with most of your wardrobe.

How to Wear Boots for Ladies

Boots are such a classy way to elevate an outfit, and the right pair can completely change the vibe of what you’re wearing. Depending on the style of boot, you can go casual, dressy, or a little bit more modern and effortless. Here’s how I like to wear the most popular types of boots:

How to Style Ankle Boots

Wide Leg Jeans with Ankle Boots

Ankle boots are so easy to style under jeans and pants. You don’t need to worry about the shaft height being too high or too low for your outfit. When wearing boots with wide leg jeans, I usually opt for a heel. The wider drape of the jeans lay the best with a little lift.

When it comes to the heel shape, block heels tend to look a little more casual than skinny heels. Either are fine to wear day and night, but I usually reserve my skinny heel boots for night time, and stick to block heel boots during the day. When wearing wide-leg jeans, ankle boots are always my top choice (I’m wearing these boots above), styled with these wide-leg jeans.

 

Straight-leg Jeans with Ankle Boots

I actually think straight-leg jeans are harder to style than wide-leg jeans. Balance is key with them. When it comes to deciding which boots to wear with straight leg jeans though, I always go for ankle boots. Again, the heel style will depend on whether you are going for a more casual or elevated look. Round and square toe boots tend to lean more casual, while almond and pointed toe boots lean dressier.

A great style that can easily go casual or dressy are the boots I’m wearing above. The block heel combined with the pointed toe makes them super easy to wear just about anywhere. Take 1/2 size up if you plan to wear these with thick socks.

 

Dressy Ankle Boots

A skinny heel always makes boots look dressier. A great way to make twill or corduroy pants look ready for night, is to add a pair of thin heel boots. Your outfit instantly gets more elevated. I love these classy ankle boots that are the perfect heel height in my opinion (70mm or 2.8 inches). The pointed toe is not restricting at all, and the leather is buttery soft. Take 15% off with TARA15. When you want to dress-up an outfit, try thin heel boots.

 

Ankle Boots with Dresses and Skirts

Wearing ankle boots with dresses is a popular way to style boots. However being petite (I’m 5’2″), I hesitate unless my skirt is long enough to only showing a sliver of leg. Having too much space between the skirt hem and top of the boots can cut you off, making you look shorter. You can get away with styling ankle boots with a maxi skirt or traditional midi skirt (meaning not a petite length). Otherwise my go-to choice will still always be knee-high boots. I’m wearing these boots (take half size up if you plan on wearing thick socks).

How to Style Chelsea Boots

Straight-leg Jeans | Fair Isle Sweater | My favorite white tee | Chelsea Boots | Suede Bag | Necklace 20% off with TARATMV | Earrings 20% off with TARAT-20

Chelsea boots are a more casual boot style and look best with jeans. The beauty of them is that they work with just about every cut from straight-leg jeans, to wide-leg jeans, they can be tucked into skinny jeans, and even go under flare jeans.

You can also style Chelsea boots over leggings with a long coat for a casual but chic layered look. It’s one of those outfits that still looks polished but is truly casual. They are a great option when you want something warmer or more elevated then sneakers.

How to Style Knee High Boots

Knee-high Boots with Dresses

When it comes to wearing dresses and skirts in cooler weather, my go-to is always knee-high boots. They not only cover your legs (and keep you warm) more then ankle boots do, but they are so classy and effortless.

I have many different knee-high boot styles in my closet. I choose suede boots when I want a more effortless look, leather when I want to be a bit more dressy, and slouchy boots when I want that cool-girl vibe. When it comes to color, the classic trio of black, tan, and ivory always works.

How to Wear Riding Boots

Turtleneck | Plaid skirt | Riding Boots (take 15% off with SF-TARA-15) | Suede bag | Cashmere scarf (more affordable option) | gold bangle bracelet | Gold Earrings (take 20% off the jewelry with TARATMV)

True riding boots are knee-high, minimal, and have a low heel. They are designed to fit in stirrups so hardware is usually minimal to none. However fashion riding boots generally have a buckle or strap giving them an equestrian edge. Riding boots always look timeless when styled with skinny jeans, a sweater, and a blazer. But you can also style these boots with dresses and skirts.

What I love about riding boots is that although they are more of a casual boot style, they can look dressy when styled up. They have a way of taking a dress or a skirt and making it more casual while still being super classy. When you want to make a dress or a skirt feel more casual, try riding boots.

How to Wear Over-the-Knee Boots (the Modern Way)

Over-the-knee boots, or thigh-high boots, can be a statement depending on how you style them. I think they tread a fine line but can be really classy when done right. They are especially chic when styled with a midi dress, or even a shorter dress that skims just above the boots.

If knee-high boots often hit awkwardly at the middle of your knee, then over the knee boots can be a really great alternative. When choosing a fabric, I prefer suede over leather for this boot style. since suede has a way of making an outfit feel more effortless and relaxed.

 

How to style western boots

Dress | Lace top (also love this one) | Straight leg jeans | Bag | Western boots (shorter leather style here)

Western boots usually have a pointed or slightly rounded toe, block heel, and decorative stitching that give them their signature cowboy look. To keep them looking timeless and not overly trendy, I would style them with slim straight-leg jeans and a white top (a top like this one to keep it feminine), or even a dress layered under a jacket. Since western boots are a statement on their own, they are great for wearing with more minimal outfits.

When to Wear Suede Boots

I tend to reach for suede boots when I want to add a softer, more casual vibe to my outfits. Leather has that beautiful sheen that instantly feels a little dressier, while suede’s matte texture makes an outfit feel more relaxed. It’s a subtle detail, but one that really changes the mood of a look.

Weather also plays a role in when I wear suede over leather. Suede is more delicate and susceptible to water and stains, so I always recommend treating them before stepping outside. A suede protector spray can go a long way in keeping them looking fresh (I like to give mine a light coat at the start of the season). For day-to-day upkeep, a suede brush is a simple tool that revives them and keeps them from looking worn too quickly.

What to Wear With White Boots

I love wearing white or ivory boots as we transition from winter into spring. They give you the warmth and comfort of boots but feel lighter and fresher for the new season. One style rule I follow with white boots is to make sure there’s another touch of white or cream in your outfit. It could be a floral dress with white in the print, a cream sweater paired with jeans, or even a light scarf. This helps the boots feel cohesive with your look rather than stark or out of place.

FAQs: How to Style Boots

Can I wear knee-high boots with wide-leg jeans?

I wouldn’t wear knee-high boots with wide leg jeans. Here’s why. Depending on the shaft height of your boots, the top of the boots can stick out and look like a bulge. Even if they look ok under your wide-leg jeans when standing, try sitting down. I don’t find them to be very comfortable unless the boots have a nice slim fit. I would style my wide-leg jeans with ankle boots instead.

Are Chelsea boots appropriate for work?

Chelsea boots tend to be a very casual style. So if you work in a very casual setting, they can work. However I would reserve Chelsea boots for a relaxed weekend style.

 

Choosing the right pair of boots for every outfit is mostly about personal taste, but there are some boot styles that really take a look to the next level. Keep in mind texture, heel style, toe shape, and shaft height when deciding what boots to wear. I hope this post helps make getting dressed a bit easier.

If you love shoes like me, you may also want to read my post on what shoes to wear with wide-leg pants.