Dressing for Different Types of Booties

Jeans for every style bootie

When I asked what type of fall content you were looking for from me this year, the topic of dressing for different types of booties came up quite a bit. Mastering this has taken me a few years, but I finally feel confident in my theories and I’m excited to share them with you today. The guidelines I’m sharing will really make an impact if you’re petite or if you have short legs. If you’re tall with long legs, you can literally get away with anything, so you do you. I wrote a post last spring, 10 Tips to Help You Dress Taller, and this post takes those same sentiments and applies them to booties. I also wrote a similar post about petites and boots at the beginning of the year here

In the past I would only wear certain booties because my legs looked so stumpy. There was even a time I would only wear black flat booties with black skinny jeans because that was the only way my legs would look flattering. I’ve come a long way and now I have a handful of bootie styles I wear and feel good in and it’s all thanks to my little tricks to help elongate my legs. 

I’ve been meaning to pick up combat boots and more of a cold weather boot. Once I do, I will update this post on how I would style those. I will keep you updated. 

Bootie Styling Guidelines

  • First and foremost, booties look best with high-waisted bottoms – jeans, skirts, pants, etc. High-waisted jeans allow for more leg to be shown, which is always what you want when you wear booties. 
  • Wearing the same color boot and jeans (black on black) help elongate your legs. I like to do this with flat boots. 
  • For ankle booties (that you will tuck your jeans into), opt for booties with a low shaft. If you tuck your jeans into a bootie with a tall shaft, you cut off your legs and you look stumpy. You want to show as much of your legs as possible.
  • Ankle booties should be paired with skinny jeans that are tight around your ankle. Don’t roll under or cuff. This also gives the illusion of stumpy legs. You want smooth and streamlined jeans.
  • If you get a bootie with a shaft, wear them with cropped straight or wide legged jeans. 
  • Sock booties are meant for cropped straight or wide legged jeans. 
  • The only time you can get away with sock booties over jeans, is when it’s a black boot and black jeans. This works because the black on black gives the illusion of one piece. 
  • Booties with tall shafts look great with midi or maxi skirts and dresses.

Chelsea Booties

These are a long-time favorite boot. I’ve had these for a good 3 years and they’re holding up well. They look great with black high-rise skinny jeans or tight-at-the-ankle high-rise dark blue skinny jeans.

Marc Fisher booties

Marc Fisher Chelsea boots

J.Crew coat petite xxs (fits snug), Madewell sweater (last year, but this year’s version is identical), Madewell jeans petite 23, Marc Fisher Chelsea boots 5, Quay sunglasses

Pointed Booties

Pointed booties are my favorite style, I love the way they look and how they elongate your legs (notice a theme here?). These have a taller shaft, so I only wear these with cropped straight or wide legged jeans. I absolutely love the color on these and the small heel is comfortable and flattering on my legs.

Tamara Mellon Hustler Bootie

Tamara Mellon Hustler Bootie

Ann Taylor coat petite xxs (old), Majestic Filatures turtleneck xs (old, new version), Banana Republic jeans petite 24 (cut hems), Tamara Mellon booties 5 (run small, this color is old), Staud bag, Quay sunglasses

Pointed Stiletto Booties

These are a recent purchase and I’m obsessed! I love the way they look with skirts and dresses, but they pair really well with jeans as well. I will probably wear these with straight or wide legged cropped jeans and I may wear them with faux leather skinny pants or black skinny jeans (and tuck in my jeans). The stiletto heel makes these a little more dressy compared to a chunky heel, which will be perfect for the holidays coming up.

Stuart Weitzman sock booties

Pointed Stiletto bootie

Topshop blazer petite 0, Majestic Filatures turtleneck xs (old, new version), Halogen skirt petite xxs, Stuart Weitzman boots 5, Quay sunglasses

Ankle Booties

I was actually going to replace these booties with these from Sam Edelman because I like a pointier heel, but ended up keeping these because they literally have zero shaft and really show all of my legs. The shaft on the Sam Edelman pair was too tall for ankle booties (they made my legs look too stumpy). While the round toe on these aren’t my favorite, the boots are super flattering on my legs and I love the brown color.

Ash Brown booties

Ankle Booties

Abercrombie & Fitch coat xxs, J.Crew sweater xxs (old, similar), Banana Republic jeans petite 24 (old, similar), Ash booties 5 (old, same style), Anine Bing sunglasses

Sock Booties

I bought these booties last year and still really love them! They’re a classic shape and the sock shaft isn’t too high, so if I need to wear them with black skinny jeans, I can easily pull it off (my only exception is when it’s black on black). These pair best with high-waisted straight or wide legged jeans.

Steve Madden sock booties

Sock booties

Asos trench petite 00, Majestic Filatures turtleneck xs (old, new version), Topshop jeans petite 25 (old, similar), Steve Madden sock booties 5, Quay sunglasses

Embossed Bootie

These were a random purchase maybe 3 years ago, but I didn’t start wearing them until last year (I bought them when I didn’t know how to style different booties). I LOVE these boots. It’s the shape, heel height, and embossed details. Since there’s a little bit of a shaft I typically wear these with high-waisted straight jeans. I love that they’re comfortable to walk in (short heel), but still give a little extra height. The leg opening is also really narrow (but still comfortable) and fitted around my ankle, making them extra flattering.

Zara booties

Embossed Bootie

Topshop coat petite 0 (old, new version), Majestic Filatures turtleneck xs (old, new version), Topshop jeans petite 25 (old, similar), Zara booties 5 (old, similar), Janessa Leone hat, Cuyana bag, Quay sunglasses