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5 Ways To Wear Ankle Boots

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Clearly, I must have shoes on the brain this week! First, we spoke about my favorite over-the-knee boots and now, we head down low to the ankle. In my styling work, one of the most frequently asked questions I get is about how to wear ankle boots.

“Should I be wearing my booties with long jeans? Skinny jeans? Cuffed jeans? Scrunched? With socks? Without?”

Lots of questions, people… lots of questions! Fortunately, today I have the answers! Actually, 5 of them.

1. Ankle boots with skinny, ankle-length jeans.

Like peanut butter and jelly, these two were just MADE for each other. If you’re a tall girl like me, by default, most skinny jeans probably fall into the ankle-length category. If you happen to be on the more petite side, most retailers and denim designers offer jeans in an official ankle-length. That small sliver of skin makes the whole look appear in proportion and visually interesting.


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2. Ankle boots with cuffed, skinny jeans.

So you’re next question is probably, “Well, what do I do with my FULL-LENGTH skinny jeans?” No worries, you can wear them too. Give them a little cuff at the bottom and they’ll look fantastic with any ankle boot.


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3. Ankle boots with boyfriend jeans.

Speaking of cuffs, boyfriend jeans are a perfect choice if you’re looking for another more casual, cuffed alternative. The slouchier the better.


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4. Ankle boots with socks.

No joke. Really, this works. Pick a pair of your coziest, marled cotton, or wool socks and scrunch them over a pair of skinny jeans or leggings for that “Fall/Winter by a roaring fire with hot cocoa” look.


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5. Ankle boots with skirts.

Fall is the time to trade in those heels for a more comfortable, fuller-coverage option. Whether straight or flared, ankle booties work well with most skirt/dress silhouettes. If you’re on the more petite side, try to stay away from longer skirt lengths to avoid any dowdy Little House on The Prairie ensembles. Oh, and tights are definitely a DO for all once the winter chill sets in!

Have you guys seen these FLEECE LINED TIGHTS?! Winter game changer.


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Shop the look:

How do YOU wear your ankle boots?
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