How To Style Ankle Boots For Fall

ashley wearing a cream colored sweater, black cropped pants, and cognac ankle boots with a leopard tote bag

Ankle boots are one of my most worn shoes for the fall and winter, but they can be tricky to style. I find this is especially true with all the denim styles that are popular today (straight, skinny, full length, cropped, flared, and more!) Today, I’m sharing some tips I’ve learned for styling your ankle boots plus 6 different outfit ideas.

This exact pair of boots are from ABLE (I shared a post about them here!). They have a mid-shaft and a semi-wide ankle, meaning the shaft is not short or tall and the width at the top of the boot is not wide or tight.

Sweater // Cropped Pants // Boots // Sunglasses

Tips For Styling Ankle Boots

  1. My first tip is to look for ankle boots with a taller, tighter shaft which are more on trend (and timeless) than those with a short, wide shaft. They also keep your ankles warmer in the winter!
  2. If you’re wearing a boot with a wider shaft, it’s best if you jeans or pants hit right at the top of the shaft rather than above it. This may mean that some jeans just don’t work with every pair of ankle boots.
  3. Try to minimize the skin showing between the top of the shaft and your pants (1/2 inch max!)
  4. Also try to minimize any bunching of your jeans at the top of the boot (either roll the jeans up or tuck them into your boots).
  5. If you’re wearing a boot with a tight shaft, it looks best if the pants or denim lay over the boots rather then tucked into it.
  6. Look for an ankle boot with a pointed toe to help elongate your legs (petite girl tip!)

Five Outfits With Ankle Boots

LOOK ONE
ashley wearing a rust colored patterned peasant blouse, medium wash mom jeans, and cognac ankle boots
Top (old from Madewell; similar) // Jeans (similar option) // Boots // Belt (old; similar)
LOOK TWO
ashley wearing a black t-shirt dress // tan long coatigan, cognac ankle boots, and a leopard print tote bag
Sweater Blazer // T-Shirt Dress // Boots // Bag (old from Target, similar)
LOOK THREE
ashley wearing a brown tee, black blazer, black floral midi skirt and cognac ankle boots
Tee // Blazer (old from Old Navy, similar, similar) // Skirt (old from Madewell, similar) // Boots
LOOK FOUR
ashley wearing a plaid blazer, gray tee, and full length medium wash straight leg jeans, with cognac ankle boots
Blazer (sold out; similar, similar) // Tee // Jeans // Boots
LOOK FIVE
ashley wearing a faux leather moto jacket, washed black graphic tee with the words Nashville, washed black denim, cognac ankle boots and a brown beanie
Tee // Faux Leather Moto Jacket // Jeans (old from Madewell; similar in same style) // Boots // Beanie

I hope this post was helpful! Styling your ankle boots, especially with jeans can be a bit confusing; so just try out a few different pairs and see what you like. On my wish list for my winter capsule are a pair of black boots with a tight shaft for wearing under some straight leg jeans. I love that look. You can also style your ankle boots with a midi or maxi dress. (See some outfit inspo here.) As always, style has no rules so wear what you love.

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