SIMILAR JACKET  ||  MERRICK’S ART FOR GOLDEN TOTE SWING DRESS (no longer available, similar here and similar maternity dress here)  ||  ANKLE BOOTS c/o RACK ROOM SHOES  ||  BAG MADE BY ME, TUTORIAL HERE, PURCHASE SIMILAR HERE 
Ankle boots have been trendy for years now, and they’re one of my very favorite styles of shoes to wear. But this year we’re seeing taller ankle boots, which tend to be a little trickier to style without cutting off the line of your leg and making you look stumpy. Obviously not what any woman wants, right?
Today I’ve teamed up with Rack Room Shoes to style these pretty zipper embellished ankle boots. Their buyer and style expert, Alyson Stanley, says that ankle boots, especially with chunky heels and zipper and strap details are huge this season — and I couldn’t agree more! The shaft of the boot is taller than any other boot in my closet, so when I went to style them I found it harder than I expected. So I came up with these two outfits for day and night, and three tips for styling them. 
1. Dress it up. To keep your leg looking long and lean, stick with knee length or shorter hemlines. Midi length dresses with tall ankle boots exposes only a few inches of leg and unless you already have legs a mile long, will make you look really stumpy. Swing or A-line style dresses are also more flattering than pencil dresses with this style of boot. 
2. Get the skinny. If you opt to wear pants or leggings with them, keep the legs and ankles on these pants really slim. You don’t want any fabric bunching around your ankles creating bulk. You can cuff your jeans, but I found that with these tall boots, it also shortened my legs when my jeans had to be cuffed so many times just to get above the boot.
3. Show a little leg. Well, I mean when you’re wearing jeans, leggings, or pants. An instant way to elongate your leg is by showing your ankles. When there is no opening between the top of your boots and the bottom of your pants, it can often create a stumpy look. Cuff your jeans, wear leggings, or style them with a shorter pair of pants just so an inch or two peeks out above your boots. [note, with dark blue or black skinny jeans, you can wear them tucked into the boot as long as they’re really fitted at the ankle and keep your ankles looking slim). 
Hope these tips help as you style your ankle boots this season! 
photos by rad and happy | created in partnership with rack room shoes


  1. Natali says:

    Such a stylish mommy to be! The first outfit is top notch and you could wear it even while not being pregnant.

  2. I’m loving those booties, the detailing is so cute.

    Kristina does the Internets

  3. The booties are so cute! Love your style!!

  4. Paige Cassandra Flamm says:

    These are great tips! I find I often look stumpier than not… so I’ll definitely be cuffing my pants from now on!


  5. Heidi D. says:

    I love your style! The zipper detail on those booties is so unique!

    Wishes & Reality

  6. These boots are so cute! I love how you showed them in a variety of different outfits 🙂

    Dani |

  7. allie J. says:

    Ugh it’s so easy to look stumpy when you wear shoes that cut you off at the ankle! Thanks for the tips 🙂

    allie J. |
    modern mid-century sewing and style.

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