12 Ankle Boot Outfits

During the fall, ankle boots are my outfit staple. I get questions all the time about which ones are the best and how to style them, so I’ve rounded up some of my favorite pairs and different ways I’ve worn them.

This week there will be a TON of great sales for Black Friday and Cyber Monday, so take advantage of the discounts and snag yourself a pair!

I’ll be sharing the best sale deals on the blog all week, so make sure you check back!



Black, white, and brown is one of my favorite classic combos. These black ankle boots are so comfortable and the mid heel height makes them really easy to wear and walk in.


Splendid Cardigan  ||  Ankle Boots  ||  Felt Hat  ||  Tassel Bag

I love a long cardigan and this one is perfect for travel or something because it’s super lightweight and comfortable. But I love it dressed up a bit with jeans, ankle boots, and a hat.



This pair is my most classic. Just a tall height, no frills, medium brown boot. They’re perfect for pretty much any outfit or any occasion. You must invest in something like these!

Merrick's Art Dress and Ankle boots

DRESS ||  military jacket  ||  BAG   ||   Panacea necklace  ||  Vince Camuto boots

An easy way to dress down your LBD is to add flat ankle boots and a casual jacket.


TOP (similar tops here, here, here, here and here)   II  JEANS  II  BOOTS

A pretty top, dark skinny jeans, and neutral ankle boots. Not many outfits much easier than that!

Merrick's Art Dress and Ankle boots

NECK SCARF  ||  CHAMBRAY  ||  WHITE DRESS  ||  SIMILAR STYLE ANKLE BOOTS (another good styling option here)

A pair of light tan ankle boots is super flattering, especially when paired with a dress or skirt.

Merrick's Art Winter White's

SWEATER (wearing size small)  ||  SIMILAR JEANS  ||  ANKLE BOOTS  ||  BAG  ||  SUNGLASSES

Pair your ankle boots with an all-white look for a chic and cozy fall/winter outfit!

Merrick's Art Vest and Stripes

VEST, on sale (similar here, on sale!) ||  TURTLENECK  ||  JEANS  ||  SIMILAR ANKLE BOOTS  ||  BAG (one sale!)

A vest is a great layering piece for those days when the weather isn’t too cold. Also I cannot live without my striped turtleneck during the fall and winter — it’s a layering staple, but also can easily be worn alone.

Merrick's Art Tunic and Ankle boots

TUNIC DRESS  ||  SIMILAR JEANS  ||  ANKLE BOOTS c/o RACK ROOM SHOES (so comfortable and come in 3 other colors)  ||  NECKLACE

If a dress is too short on me, I throw on my skinniest (a.k.a. most elongating) pair of skinny jeans and a pair of ankle boots.


SHIRT (sold out in this color, but more colors available! It’s so soft, lightweight, and comfy!)  ||  JEANS  ||  ANKLE BOOTS  ||  BAG c/o FAWN DESIGNS  ||  SUNGLASSES


TOP  II  SKIRT (unavailable but find similar one here)  II  BOOTS

Boots are great with pencil skirts! Just choose more narrow boots so your leg line isn’t broken.


JEANS  ||  SWEATER  ||  WEDGES (limited sizing. Also available in black here, and a similar pair here)

A good pair of wedge boots is a great way to get height with a lot of comfort. These ones are so comfortable and are a good neutral brown that goes with everything.



  1. April says:

    This is such a timely post. Last year I had one pair of black suede booties and I bought a strappy pair of black leather boots. I also had a pair of black riding boots and a pair of brown and taupe suede booties. It felt so excessive bc boots are expensive and large. This fall I found some awesome distressed pewter/silver ones that I love and wear often. I wanted a red bootie and a blue bootie and was feeling like that was just way too many boots. I was talking to my friend and she reminded me that I had every color of flats and sandals in the rainbow, why shouldn’t I have variety in my boots? Excellent point. I found this amazing pair of black L.K. Bennett Chelsea boots that are cobalt blue on the back piece and black in the front, and a pair of black leather boots with red straps, and a pair of really strappy black ones similar to what you are wearing above, and I’m eyeing those Vince Camuto ones you have above in black. I need some color and variety in my winter footwear bc winter lasts for sooooo long here. I’m gonna check out the ones you shared.

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