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The Ultimate Guide to Styling Boots & Booties

December 28, 2021


Erin Schrader

Booties, booties, booties rockin’ everywhere! When it comes to Fall and Winter fashion, boots are my weakness. Every year I look forward to the new “trendy” styles, even if that means having no clue how to style them. Ya feel me? They’re fun, but I get it. They can be tricky! Nevertheless, I’m a firm believer there’s nothing better than leggings, boots, and an oversized sweater this time of year. Unfortunately, you can’t always get away with wearing that exact outfit every single day to every single occasion. That’s why today, we’re sharing 7 trending style of boots and over 35 ways to style them. From sock booties to over-the-knee boots and every style in between, here is your Ultimate Guide to Styling Boots and Booties!

Classic Ankle Booties

Brynne Ankle Bootie [TTS]

Let’s start with the basics! These classic ankle boots are a wardrobe staple, and chances are, you probably already have a pair [or several, no judgement here! 😉 ] in your closet! They tend to have a short shaft [don’t giggle, Erin, don’t giggle], block heel, pointed toe, and match just about anything! If you don’t already own a pair of ankle boots, I highly suggest investing in a pair or two. This is a timeless style that’s not going anywhere. You’ll be wearing these for years to come!

Shop Ankle Booties Below:

Mid-Rise Ankle Boot

Leather Block Heel Ankle Boot [TTS]

The next style is just a step up from the basic ankle bootie! This boot has a slightly taller shaft and, in this case, is elevated with a leather material. Since these are on the dressy side, you can get away with wearing them to work with dress pants or for more formal events that require dresses and skirts! Again, if you don’t already own a pair, this is a classic boot that will get plenty of wears!

Shop Mid-Rise Ankle Boots Below:

Sock Booties

Sock Booties [TTS]

Now for the fun stuff! The sock bootie has been making an appearance the last few seasons and I’m FINALLY hopping on the bandwagon. Trying new things can be hard, right? Sock booties are great because you can style them with your everyday denim, but they also pair well with skirts and dresses! If you’re going for a more elevated, stylish look for any events this season, consider reaching for a sock bootie!

Shop Sock Booties Below:

Classic Chelsea Boots

Chelsea Boots [TTS]

Moving onto the classic Chelsea Boot! Chelsea Boots are fitted, often have an elastic side panel, and loop on the back to help pull ’em on. This pair, as well as a the majority of Chelsea Boots you’ll find, are water resistant. I love that they’re not as clunky as traditional rain boots and are stylish enough to be worn throughout fall and winter.

Shop Chelsea Boots Below:

Chunky Chelsea & Combat Boots

Chunky Chelsea Boots [TTS]

If you’ve been keeping up with trending boots this year, chances are you’ve come across the chunky chelsea. While they’re very similar to the sleek, classic Chelsea, these have a much thicker sole and a more prominent heel. When it comes to this style, the chunkier and clunkier, the better! I was a little bit hesitant to this style at first, but I’ve grown to love throwing these on to elevate more casual outfits. To summarize, they make me feel a lot cooler than I actually am. I’m not sure if this trend will stick around for seasons to come, so I opted for a budget-friendly pair from Amazon!

Shop Chunky Chelsea Boots Below:

Slouchy Knee-High Boot

Slouch Boot [TTS]

Every year, we receive DM’s asking if knee-high boots are still in. Here’s the thing. I’m a firm believer that knee-high boots are always in! And if you love them, wear them! While the style of on-trend boots may change [ex. leather riding boots vs. slouchy suede] each season, they always seem to come back around. All this to say, if you love your boots, rock them! This style pairs great with slim, skinny denim, leggings, and dresses or skirts.

Shop Knee-High Boots Below:

Over the Knee Boots

Over the Knee Boot [TTS]

Last, but certainly not least, is the Over the Knee style! These can be especially tricky because of factors like height, inseam, calf or thigh thickness, and so on and so forth. Don’t be discouraged if you haven’t found the perfect pair yet! They can be too tight, too loose, too tall, not tall enough, etc. Don’t give up – they’re not one size fits all! If you’re lucky enough to find a great pair of OTK boots, consider yourself a lucky girl. These work best with skinny denim, leggings [especially faux leather!], or dresses and skirts that hit above the boot!

Shop Over the Knee Boots Below:

Shop All Boots from Today’s Post Here:


Shop All Bottoms in Today’s Post Here:

Shop All Tops in Today’s Post Here:

share this with your best girlfriends:

  1. Rachel says:

    Can you share the links to the jeans too?

  2. Beth says:

    Great post! Thank you.

  3. Megan says:

    Thanks for the tips? What about sorel ankle booties? I just got the Evie wedge bootie in a caramel color and my jeans bunch up on them!!

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