Style - November 11, 2019

How to Wear Ankle Boots

Have you noticed how many bootie options are out there? Pointed toe or rounded toe, tall shaft or short shaft, leather or suede, block heel or stiletto heel? There are hundreds, no thousands, of different options. So, how do I know which type of bootie to wear? While there are no hard and fast rules, there are some guidelines I follow that help me when I consider wearing booties.

Figuring out what makes a bootie work and why is what I want to focus today’s post on. But in order to fully answer that, I wanted to first talk about all the bootie styles you’ll find out there – at least popular ones. Because figuring out how to wear booties has a lot to do with what kind you’re trying to wear. It’s also important to know that certain styles of booties are more limiting than others and tend to work better with particular styles (e.g., rolled up jeans, a dress, leather leggings, etc.).

What are the Different Types of Booties?

After years of putting together outfits, I’ve realized that I definitely¬†need multiple styles¬†of booties to make what I have in my closet work. In other words, one style of bootie doesn’t really fit all outfits. Wouldn’t you agree? And it can be challenging to know which style/color bootie is going to be my “winner” for the season – aka the one I actually wear more than once. It’s so frustrating when I think I’ve found the cutest bootie ever, I buy it, and then I’m only able to wear it like 2-3 times that season. I think we all know how that goes, right?

how to wear booties

I wanted to point all the different distinguishers out because I think it helps facilitate the booties conversation (ha!). It just kinda shows y’all what I mean when I say “low shaft, tight ankle” or “mid-shaft, semi-wide ankle”, etc. But now that we’ve gotten that out of the way, we can jump into the different ways to style each type of bootie!

I went back and forth on how to organize this post – whether I wanted to talk about the different characteristics of booties and how to style each of them or whether to start with clothes and talk about which bootie work with each style. Well, let me tell you that I have now re-written this post THREE times and I think the way I’ve got it laid out here is the MOST helpful!

I truly hope from the bottom of my heart that this blog post helps serve your styling needs in some way or another! As always, please don’t hesitate to leave comments below and ask questions! I’m here to help!

Before diving into the post and all that I have to say about styling booties, I thought it might be helpful to provide this little flow chart for yall, outlining all my findings with how to style which boot with what. If you want the full resolution version to print out, you can download it here!

the Outfit Guide

Current Favorite Boot

Mid Shaft, Tight Ankle Bootie

This bootie has been the ones that I’ve been grabbing the most often lately. I’ve been able to style it with just about anything – from leggings, to skirts, to dresses (both long and short), to cuffed jeans, rolled under jeans, cropped jeans and more! I love the mid shaft and that the ankle is tight but not *too* tight to where it cuts off your ankle. It runs true to size but if you want room for a thick-fish sock, I’d recommend going up a size.

How To Wear Booties With Jeans

Now that we have a good understanding of the different options out there, I thought I would dig into specific outfits and what types of booties work best for each outfit type.

In this section of the post, I’ll be covering how to wear booties with skinny jeans and then how to wear booties with wider leg jeans such as mom jeans and straight leg jeans.

how to wear skinny jeans with booties

How to Wear Booties with Skinny Jeans

Skinny jeans are my most often-worn pant – I just LOVE them! They are flattering, can be dressed-up or dressed-down, and are easy to style.

I’ve found that when it comes to wearing skinny jeans with booties, you’ve got TWO main camps of styling depending on how long your jeans are: regular length skinny jeans and cropped.

First, let’s discuss wearing booties with cropped skinny jeans then we’ll move into regular length.

Wearing cropped jeans with booties has recently become super popular since first writing this post back in 2016. I personally love wearing cropped skinny jeans with booties and think it looks super chic and very neat too!

Outfit Details: cozy sweater // cropped jeans // snakeskin booties

The key to wearing cropped jeans with booties is that you want the hem of your jean to either meet the top of your bootie shaft or stop before. In the look above, the hem of my jean hits right at the top of the bootie. This looks great!

If the hem stops before, then you’ll be showing a little bit of skin.¬†So then the question becomes, how much skin do I show?

Notice in this second look, I’m showing more skin than the previous outfit. This is because the booties have a lower shaft (the jeans are the same). I think showing any more skin than THIS is too much. It just starts to look funky in my opinion. As a general rule, stick to anything between no skin and two finger widths of skin between the bottom of your hem and the top of the bootie.

On the other hand, if your jeans are the length of your leg (aka not cropped), then you’ll either be rolling them up, rolling them under, or tucking them into your booties. We’ll cover this in the section below.

What About When Your Skinny Jeans Are Long?

In other words, when your jeans are not cropped.

Usually, when we buy jeans, we buy them to fit the length of our legs. They look great with normal flats or even sneakers, but when you try and wear normal length jeans with booties, you have an issue. And that is the fact that your jeans and bootie overlap a little bit: the shaft of the bootie goes up your ankle and runs into the bottom hem of your booties. This “overlap” can look pretty messy and bunched up, which is why it has become so popular to ROLL your jeans up.

In this section, I want to discuss the different ways you can wear your jeans with booties when your jeans are FULL length. Some jeans are cropped (so you don’t have the bunching issue – we’ll get to that in a minute!).

how to know whether to tuck your jeans in or roll them up when wearing booties
Outfit Details: Good American Jeans // Brown pointed toe booties // Ribbed pocket detail sweater (wearing size XS)

When you’re wearing full-length jeans with booties, you have three style options:

  1. Roll up your jeans
  2. Roll under your jeans
  3. Tuck your jeans into your booties
Outfit Details: high-waisted white jeans (fit true to size, I got the short version) // sweater (wearing size XS) // white booties (fit true to size)

First, I do want to mention that I’ve found showing a little skin by either rolling up or under my jeans elongates my legs. Note how in the photo above I have one leg tucked in and one rolled up. I think they BOTH look great but for some reason rolling up my jeans (and showing a little skin) always makes me feel better and I think it’s oftentimes more flattering. I realize this isn’t always possible though when it’s super cold outside. OK, moving on!

Now let’s discuss when to roll up vs roll under vs tuck in your jeans!

how to wear booties with skinny jeans rolled up

Option 1 with long jeans: Roll up your jeans

Rolling your jeans “up” gives your outfit a more casual vibe. Therefore, when wearing a casual bootie, like a rounded-toe suede bootie, I tend to roll my jeans “up” to complete the casual look. The last rule of thumb for a rolled jean is to wear a shorter shaft bootie. Tall shaft booties and a rolled jean cut up your leg too much. Therefore, when rolling my jeans, I always choose a shorter shaft bootie.

Option 2 with long jeans: Roll under your jeans

I always roll my jeans under if I’m looking for a more polished look or if I’m wearing a tall shaft bootie. Tucking the jean under creates a cleaner, more chic look. I usually tuck my jeans under for date nights or when wearing a fancier jean (like a coated black jean). I also ALWAYS tuck my jeans under when wearing a tall shaft bootie. This creates a more elongated look. In general, tucking under creates a more elongated look in comparison to a rolled jean.

brighton keller at pumpkin patch wearing cream sweater black jeans and tan booties with bucket bag and sunglasses
Outfit Details: Jeans // sweater // booties

It’s a little hard to tell here (above), but I rolled under my jeans so I could show a little ankle since I thought it looked more flattering! If I didn’t roll them under, they’d be all bunched up at my ankle.

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Option 3 with long jeans: Tuck your jeans into your booties

There are no hard and fast rules for tucking a jean into a bootie. It truly depends on the jean and bootie combo. I try to avoid the bulky look when I’m tucking a jean in, though so I usually tuck a skinny jean or legging into a wider shaft bootie.

In this look above, you can see that the booties have a wider shaft opening. In this case, I think a super skinny jean looks really great tucked in because there’s room for the jean.

Outfit Details: Black bodysuit (wearing size XS) // Good American jeans ($99 – fit TTS) // Leopard booties

It also works great to tuck skinny jeans into booties with a higher shaft that have a wider opening like these booties above. It’s kind of hard to tell in the photo, but the shaft of this bootie is not tight around my leg so there’s room for the jeans to be tucked in without them bunching up!

Also wow I need to clean my mirror…

faux leather leggings with oversized sweater

Outfit Details: This look is old but the leggings are still in stock and I love them so much! I wear size small.

And same with faux leather leggings like in this look above! Since the leggings are tight to my leg, they look nice when tucked into a bootie – regardless of how high the shaft is.

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how to style booties with wider jeans

How to Wear Booties with Non-Skinny Jeans

In this section, I’ll discuss how to wear booties with mom jeans, straight leg jeans, cropped flares, and long flares.

I could be wrong in making this gross generalization, but I feel like wider leg jeans are just recently a thing like in the last 2 years. Maybe it’s just me, but I didn’t own a pair of mom jeans until the 90s started coming back in style towards the end of 2017. And now I have a pair of mom jeans, boyfriend jeans, straight-leg jeans (wider than skinny), AND some flared jeans too!

With all these additional types of jean hems being in vogue, we’re now presented with a new challenge of figuring out how to best wear booties with each style in a way that’s flattering and looks pulled together.¬†In this section, I want to discuss how to wear booties with all the different types of non-skinny jeans I’ve been wearing recently.

Outfit Details:White bodysuit (wearing size XS) // Jeans // White booties // Sock booties 

How To Wear Booties With Mom Jeans

I usually loathe mom jeans. I just don‚Äôt think they look that great on my frame because not only am I short but my legs are super short too for my body! But even still, I wanted to discuss mom jeans because they’re super in style right now.

In my experience, I’ve found that a skinny and high shaft (like sock booties) tend to look the best with mom jeans. The contrast of the wide leg and skinny bootie shaft makes for a great, flattering combo!

how to wear booties with straight leg jeans

How To Wear Booties With Straight Leg Jeans

These are the closest thing to a skinny jean, but instead of being super skinny around the ankle, they’re just sort of straight (not wide, not flared – just straight). And the leg is usually a looser fit – although not always. I’ve found that there are no hard and fast rules with styling straight-leg jeans – aka most booties look great with them!

Outfit Details: Straight leg jean (fit true to size) // Striped tissue turtleneck (wearing size XS) // Teddy Coat (wearing size XS) // Rounded toe booties (fit true to size)

My favorite way to style a straight-legged jean is with a tighter shaft bootie – regardless of the height of the shaft (I like both). In this look above, I’m wearing a lower shaft round toe bootie and I like how it looks! I prefer just one roll to make a cute cuff like in the look above.

How To Wear Booties With Cropped Flares

To be honest, these are the hardest to style with booties. The try-on experience for this style was truly an experiment! After trying on like 7 pairs of booties with my cropped flares from Madewell (I get petite sizing so they’re truly cropped on my short frame), I realized that a tall, skinny shaft bootie looks best. It looks best when you show ZERO ankle and when the bootie shaft is much skinnier than the flare of the jean – hope that makes sense!

Outfit Details: Flared jeans (super old J. Brand) // Snakeskin tank (LOVE – wearing size XS)

How To Wear Booties With Boot-Cut Jeans

I rarely wear boot-cut jeans (I think the last time I wore a bootcut was in high school, LOL). However, they are coming back in style and are some people‚Äôs go-to. And if you live somewhere where it’s cold, then you’re probably going to want to pair your flares with a bootie – so which ones look best? With a flared jean, the shaft doesn’t matter because you won’t see it, but I recommend pairing your flares with a pointed toe bootie because it elongates your legs!

How To Wear Booties With Dresses and Skirts

In my personal experience, there aren’t any strict rules for wearing booties with dresses and skirts. I feel like most booties “work” with all sorts of dresses and skirts and that it truly just depends on your personal sense of style and preference.

However, I will say that my favorite bootie to wear with dresses and skirts is a tall shaft with a pointed toe. This elongates my legs and the entire look! With that said, rounded toes and shorter shafts also look great. So wear whatever makes you feel most comfortable!

Outfit Details: leather mini skirt (wearing size 2) // cozy sweater (waring size XS) // Leopard booties // snakeskin booties // black leather booties
short flowy dress with booties how to wear booties with a dress
Outfit Details: Green Dress (wearing size 2) // leopard booties  // short black booties // black sock bootie
Outfit Details: Fitted Midi Dress (wearing size small) // mid shaft bootie // black sock bootie // short black booties
Outfit Details: leopard dress (wearing size xs) // black sock bootie // short black booties

I hope these looks made my point that I think all booties pretty much “work” when you’re pairing them with any sort of dress or skirt!

How To Wear Booties with Work Wear

When I asked y’all to send in your questions regarding booties, I got quite a few regarding how to style booties in a way that still looked appropriate for work. After thinking it over, I decided the best way to cover such a broad topic was to pick a few popular/common work silhouettes and then discuss the booties that look best with each.

As a general rule, I’d suggest pairing your work outfits with nicer-looking booties. Usually the material and the shape and style are what make a boot look nicer. In my experience, I think a pointed-toe leather (mid to high shaft) bootie works best for work. But again, it truly depends on your work environment and the weather too!

I chose two popular pants to style for you to give you a visual of what I think looks best.

how to wear booties to work wide leg work pant with black leather booties
Outfit Details: Wide leg pant (wearing size 0) // black bootie // white top (wearing size xs)

I think booties look great with a wide-leg gaucho pant. My main tip for styling here would be to just make sure the ankle of the bootie goes up far enough so that you aren’t showing any skin – it looks more professional that way. Also, I think a pointed-toe bootie looks more flattering in this circumstance and dresses up the look for work. What do y’all think?

skinny pixie pant with booties work outfit with booties
Outfit Details: black pant (wearing size 0) // white top (wearing size xs) // white booties

Maybe even more popular than the gaucho pant is your everyday skinny pixie pant. I used to wear my J.Crew ones almost every day for work, so I thought it would be a good option to style. I tried on a few different bootie options with these pants and I think my main takeaways are the following:

  • Don’t show too much skin – it looks more professional when the booties hit the hem of your pant
  • Go for a skinny bootie opening – you don’t want the bootie opening to be awkwardly bigger than your pants
how to wear booties with pencil skirt for work
Outfit Details: pencil skirt (wearing size 0) // black bootie // black top // blue fur jacket

I personally think a higher shaft bootie works better with a pencil skirt for work. I tried this look on with a shorter shaft and it just looked a little clunky.

Outfit Details: black dress (wearing size o) // blazer (wearing size 0) // short black booties

Again, I’d say to go for a nicer-looking bootie and opt for pointed toe. But that’s just my personal opinion!

WOW! That was a lot, but again, I truly hope this was helpful and answered all your bootie questions! Definitely let me know if something doesn’t make sense to you or if I completely skipped a scenario you need some advice on and I’ll do my best to get back to you ASAP!