Booties are incredibly popular with absolutely no signs of slowing down.  It seems fairly obvious that they should be easy to wear in the winter.  However, once it gets super cold, they can get tricky.  Do you tuck your pants into the booties?  Wear them over?  What about that gap of ankle skin between the pants and the booties?  Surely, we can’t be expected to expose skin on cold days when wearing booties, right?  Socks?  No socks?  This is way too much to think about, especially given the popularity of these shoes.

How to Wear Booties in the Winter

Below I have broken down a few ways to wear your booties in the winter.  Take a look below.

#1- Wear skinny ankle length pants that just cover the tops of the booties

booties in the winter

When looking for booties and skinny pants that will work together, look for booties that sit a bit higher on the ankles to get more ankle coverage and then select ankle length pants that just graze the top of the booties.  You don’t want a break in the pants when wearing them.  A break is when the fabric at the hem pools a bit at the instep.  You want a clean, straight line.  In looks like this, I would avoid heavy, bunchy socks and choose thin trouser like socks instead.

In the outfit above, I styled these skinny ankle pants from Vince Camuto with a pair of booties by Corso Como.  With the pants I added this sleeveless top from Theory and over that I used this cardigan from Elie Tahari.  The look is accessorized with a Rebecca Minkoff bag in burgundy, a pavé chain link bracelet from Michael Kors and Kendra Scott drop earrings.

#2- Tuck pants into the booties

booties in the winter

The next way to wear booties in the winter is to tuck your skinny pants or jeans into your booties.  Don’t force this if the pants aren’t designed to be tucked in, the pants will just balloon and you will look a pirate.  If you have to fuss to keep your pants tucked in you should just avoid it.  Also make sure the booties have a wide enough opening for the pants to be tucked.

In the outfit above, I styled these booties from Cole Haan with a pair of skinny jeans from J. Crew and added this teal sweater from Boden, yellow scarf from Steve Madden, grey bag from Sole Society and earrings from Madewell.

#3- Wear booties with tights

booties in the winter

Wearing tights with booties is a fairly obvious suggestion.  You can create a monochromatic and slimming look by pairing them in the same color together.  It’s also fun to play with different tights shades too.  I love wearing burgundy booties with brown boots.  In the outfit above, I styled these black tights from Lands’ End and booties from Caslon.  I added this dress from Madewell, bag from Fossil and necklace from Panacea.

#4- Roll your jeans to the top of the booties

booties in the winter

With boyfriend jeans being so popular, they can be easy to wear in the winter with booties.  The roll can end right at the top of the booties and, if you want, you can wear socks in an exposed scrunchy way or hidden under the jeans.  It all depends on the look you want.  I have done both.  I styled the booties from Sam Edelman and boyfriend jeans from Lucky Brand, added this long sleeve t-shirt in grey from J. Crew, navy blazer from Elie Tahari, printed scarf from Nordstrom, bag from Dara and yellow earrings from Kate Spade.

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