Ankle boots (aka- booties) are the unsung hero of fall, giving us the style versatility to match every mood. They pair well with dresses, skirts, tights or jeans… alone or with thick ankle socks… the possibilities are endless!
Certain styles of booties are more limiting than others and tend to work better with certain looks (cuffed jeans, a dress, ankle pants, leggings, etc.). Figuring out how to style booties has a lot to do with what kind you’re wearing. I’m going to list my top go-to favorites when it comes to fall booties, and I’ll also explain why each one of them work with certain looks and not others.
In order to best explain how to wear ankle boots, the different types of booties and the styling limitations of each needs to be discussed. There are four big defining factors to be considered when it comes to styling:
Toe Shape: A pointed toe bootie, regardless of the color or material, is typically going to be dressier, while a round-toe bootie can be dressy or casual depending on the material or shaft height
Heel Height: Flat-heeled booties tend to have a more casual vibe than a mid-to-high heel, however, material can play a big part in this. For example, a leather flat-heeled ankle boot can have a high-end or dressy feel to it.
Heel Style: A stiletto-heel is typically dressier than a block-heel style, and can be limiting when it comes to putting looks together. Block-heel booties are very versatile and can be worn with just about anything. Wedge booties can be a little limiting, but offer a great alternative to an everyday block-heel bootie. The material (suede or leather) and toe shape (pointed or rounded) will ultimately determine whether you can dress them up or down.
Shaft Height: Shaft height plays a big role in styling ankle booties because it is very limiting. Low-shaft heights only look good with cuffed jeans, shorts, dresses & skirts, or with a pair of thick socks over jeans. High-shaft heights look good with leggings or tucked jeans. Mid-shaft heights are my favorite, and probably the most versatile since they can be paired with pretty much anything!
So, now that we have the basic composition of the ankle boot figured out, the big question is- how to style them:
Stacked-Heel: Personally, this is the style that I wear the most often and find to be the most comfortable for all day wear. Depending on the toe shape and material, this style of bootie can be incredibly versatile. Although they can be worn with dresses, they have more of a casual, everyday vibe, especially compared to a stiletto-heel. They’re prefect for a casual brunch date or shopping day with your girlfriends.
Recommendation: I have several different colors in this style but the ones I wear the most often are my brown ones because they go with so many different looks. You can find the exact style here (fit TTS and are SO comfy!), or a similar style here.
High Stacked-Heel – Any ankle boot that has more than a 3.5” heel is going to have a slightly dressier look to it compared to a low stacked-heel style. A little bit too fancy for everyday casual wear, this style ankle boot would be a great choice if you want to elevate your look without going too elaborate. I wear my high stacked-heeled booties with just about anything (jeans, skirts, & dresses), but only when I want to look a little more polished.
Stiletto Heel: This style of ankle boot is the dressiest. They are best worn on a night out or for a polished daytime look. I like pairing this style with dresses over a stacked-heel style because it looks much more formal and instantly elevates your outfit.
Recommendation: These Michael Antonio stiletto booties are my favorite to pair with dresses or when I’m trying to elevate a daytime look during the chilly months. They are super comfy, and the leather gives them a dressy look. The mid-height shaft also makes them versatile when it comes to tucking leggings or cuffing a pant/jean. This exact style is sold out, but you can get an almost identical pair here. These pointed-toe booties are also a great option, and look really high end without the big price tag!
Flat Heel: This style is my go-to if I know I am going to be on my feet all day. They look great with jeans (cuffed if low-shaft, tucked if high-shaft), but they can also be paired with dresses or skirts during the summer or early fall months. They tend to look more casual than the block-heel booties, but there are many Chelsea style booties that are super chic and can have a dressy feel to them.
Recommendation: As you can tell by the wear, my go-to flat booties are these black leather Chelsea boots from Nine West. They are SO comfortable and are perfect for all-day wear, especially when the weather is wet and icy. They aren't super dressy, but are perfect for wearing with jeans, and the mid-height shaft allows for cuffing or tucking. This exact style is sold out, but here is a similar style with a chic pointed toe. Added bonus, they're under $100! Just be sure to read the reviews, they may run a little large.
I highly recommend also having this style in brown, so no matter what your color pallet is for the day, you have a trendy and comfy option.
And just because I feel that we all need a little help with this every now & then, here are some tips for wearing ankle boots with skinny jeans:
Tucked: Tucking your pants into your ankle boots creates a long, lean leg line. This works best with super skinny or legging jeans where the leg opening at the ankle is small and fits snugly on your leg. This look can only work with mid-to-high shaft ankle boots, trying to tuck your jeans into a low-shaft boot won’t work well, and is not flattering for your leg line.
These slouchy high-shaft booties are perfect for tucking in jeans or leggings, and the dark berry color is perfect for fall & winter.
Cuffed: When wearing jeans with booties, an exposed ankle is key to keeping your ankles looking as slim as possible. One of the best ways to create this gap between the jeans and boots is cuffing the hem. This look is best when paired with a stack-heeled bootie to help elongate your leg.
The key to pulling off the cuffed look is to not make the cuff too big, or show too much leg. Creating a 1-2" sized cuff to show just a peek of skin between the boot and the hem is the most flattering.
Layered: The sock trend is one of my favorites, especially on those extra chilly fall days. This look can be tough one to pull off though because it adds bulk to your ankles, so make sure you wear a super skinny or legging style jean. This look can be worn with either heeled or flat ankle boots, and a low-to-mid shaft height is best.
Here is an example of layering a sock with mid-shaft height & low-shaft height booties. Scrunching the sock so it sticks up above the top of the boot 1-2" is the best way to style this look.