Petite Style: How to Wear Different Style Boots

I received so many messages from fellow petites asking how to style different types of boots. It’s funny because I feel like the timing of this post is so spot on. I’ve struggled with styling boots and booties my whole life. In fact, I swore off ankle booties back in the day because I 1000% thought my short legs could not pull them off. I’ve started to wear more boots and booties over the last few years, but not until more recently, have I felt like I’ve mastered this as a petite. There’s still styles I avoid (I DO NOT wear tall boots), but for the most part, I can wear any style boot and feel confident and elongated. I’m sharing all the tips I’ve learned over the years below.

My biggest tip for anyone who’s looking to look taller in their clothes, you want to wear high-waisted everything! A high-waist is your best friend. I will go more into these tips in another post, but I thought I’d share this little tip in this post because it goes hand-in-hand with wearing boots. You want to show as much leg as possible and high-waisted pants/jeans give that illusion. I should also mention, you’re going to want to tuck in all your tops. I’m telling you, it makes the BIGGEST difference.

Wearing Zara booties (old)

Short Heeled Pointed Toe Bootie

I’ve only recently discovered how well this style works on my frame. I’ve had several boots in this style, but never reached for them because I didn’t know how to style them. These look best with cropped jeans – think cropped flare, mom, or straight. The short heel gives you extra height, but they’re still comfortable and easy to walk in. The long toe (whether rounded, almond shape, or pointed) helps to elongate your legs even though you’re wearing cropped jeans. To wear this style best, you want your boot to have a small shaft (enough to go under your cropped jeans).


See by Chloe Shearling Wedge boots 5

Snow/Hiking Boot

I’ve tried so many styles and have been really disappointed. Flat, embellished (faux fur. etc.), high-shaft boots are not petite-friendly whatsoever. There’s really no way around it. I mean, I guess you can go with a black pair and pair them with black jeans or black leggings every time. I think you could possibly get away with that. I honestly can’t believe these See by Chloe boots work and are even flattering. I lost all hope in flat snow/hiking boots, so I decided to start looking at heeled options. The wedge on these make them comfortable and easy to walk in and they help elongate my legs. I think the height of the heel balances out the higher shaft (that completely cover my ankles). With all that being said, I would still probably only wear these with high waisted jeans or leggings.

Micro Touch Water Resistant Quilted Jacket in concret snow leopard

Hunter Tall Tour Boots 5

Tall Rain Boots

I’ve styled tall rain boots many times over the years and I only recently made one change and it has made the biggest difference. Wear high waisted jeans or leggings! This will help show off more leg (because we always want as much leg as possible). Your tall boots are hiding so much of your legs, which can be so unflattering when you’re short. The extra inches of “leg” with your high waisted bottoms make all the difference.

Loft Turtleneck

Stuart Weitzman Hiline OTK boots 4.5

High Heeled OTK Boot

High heeled OTK boots might be the most flattering boots for petites. I’ve heard mixed feelings about OTK boots and petites, but trust me, if you find the right boots and you style them correctly, you will look very tall. You want your OTK boots to be slimming and form fitting to your legs. No slouch boots and don’t pick styles with thick shafts. I’ve tried many brands of OTK boots (read more here) and Stuart Weitzman is without a doubt the superior boot. Pricey, but if you wear OTK boots a lot, they’re a great investment. Again, it’s best to wear these with high waisted jeans and at tucked in top.

Ash brown suede booties

Ash Joy Booties 5 (in black)

Tall Heeled Ankle Bootie

The key to making ankle booties work for petites (this probably goes for flat ankle booties as well) is finding a pair with little to no shaft. The Ash pair that I’m wearing hit me right at the ankle. This allows as much of my leg to be seen as possible. Meaning, the shaft doesn’t cover up my legs, making them look even shorter. Pair this style with high-waisted jeans and all of a sudden you look taller than you ever thought you could.


Banana Republic Plaid mini skirt

Marc Fisher OTK boots

Marc Fisher OTK Boots 5

Flat OTK Boot

I wasn’t sure how flat OTK boots would look on me, but they actually work and are flattering. Again, find a pair that are form fitting along your legs and pair them with high-waisted jeans. OTK boots with ties have proven to be the best for me. I like to even pair flat OTK boots with skirts or dresses. But, you’re going to want to keep your dress or skirt on the short side.

Banana Republic camel blazer

Steve Madden Sock Booties 5

Sock Booties

For me, sock booties look best worn under your jeans (not over your jeans). Pair sock booties with any type of cropped denim, even a skinny jean with a more straight leg opening. And you want to make sure your denim is cropped enough for the booties. I think the jeans I’m wearing in this photo are a little long – ideally I would like more of the sock part of the bootie to show.


How to Style a trench coat

Marc Fisher Yale booties 5

Flat Pointed Toe Ankle Bootie

Flat booties in general are hard to wear, no doubt. No heel to help you out whatsoever. I don’t own a ton of flat boots, but I know it’s something you all have and need help styling. I wear my black flat Marc Fisher pointed boots at least every other day. They’ve been a life saver this winter. They’re so comfortable and instantly make you look elevated – I feel like pointed booties have that effect. I tend to wear my booties with black jeans (monochromatic) or my high-waisted legging jeans that hit right at the ankle. You want to avoid any jeans that bunch at the ankle. Your legs will end up looking stocky, which is exactly what we don’t want. If I wear my brown Marc Fisher boots, I will wear them with a complete monochromatic look.

*Monochromatic dressing is your friend when you’re petite. You can dress in all one color from head to ankle and then play with your shoes OR go monochromatic from waist to feet (shoes and jeans same color) and play with your top. Both ways help make you look taller.