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Winter skirt outfits to wear this season

2 women wearing dressy skirt outfits


Winter’s chill has already arrived, but that doesn’t mean you have to pack away your skirts until next spring. There are lots of ways to wear skirts in winter while staying just as warm as you would be in pants. Let us show you how:

2 women wearing dressy skirt outfits

How to wear skirts in the winter

What to wear underneath

The key to pulling off winter skirt outfits is to wear a warm layer beneath them. Regular old stockings and leggings won’t do – you need something designed for the cold. Look for opaque tights instead, and choose a pair lined with fleece if you want extra warmth and comfort.

“Avoid tights and leggings made of cotton or cotton blends.”

Also, you’ll want to choose a moisture-wicking fabric. Although it’s winter, you may find yourself sweating underneath your coat as you hustle through the day. Unless you’re wearing a water-wicking, quick-drying fabric like nylon, polyester or merino wool, the sweat will sit against your skin and cool down rapidly, keeping your clothes wet and uncomfortable. Avoid tights and leggings made of cotton or cotton blends; these trap water, which is the last thing you want.

What to wear over top

Often, a pair of thick tights or high boots is all you need to keep warm when wearing a skirt in winter – unless, of course, you live in a place where temperatures regularly fall below freezing. If the skirt you’re planning to wear wasn’t designed with icy winds in mind – and honestly, most of them aren’t – you’ll need something to block these bone-rattling chills. Opt for an ankle-length wool or puffer coat to keep your entire body warm. Your outfit will be hidden while you’re outside, but these coats are perfect for a dramatic reveal once you get indoors.

On the other hand, those of you who don’t live in the icy north should feel free to show off your tights and skirt with a coat that ends above the knee. For example, pairing a skater skirt with black tights and a leather or motorcycle-style jacket gives you a bit of casual edge, while a cape paired with a pencil skirt is a great office alternative to dressy pants outfits.

Style tips for wearing skirts in winter

Now that we have the basics out of the way, let’s get to the outfits! These suggestions will leave you feeling warm and looking good throughout the colder months. And as always, don’t forget accessories! It does no good to keep your legs warm if your head and fingers are freezing, so grab your gloves and hat on the way out. It’s good to have a pair of each in a basic color like black as well as a statement color so you can mix and match.

Pencil skirts

Pencil skirts are perfect for the office, making them great for wearing with sweaters, blazers and button downs. You can have a lot of fun with the length of your top here – try tucking a collared shirt into a high-waisted skirt or donning an oversized sweater that falls past your waist. Each option creates a radically different look, but both are incredibly chic. Finish the outfit with thick tights and booties or knee-high leather boots.

Woman wearing pink jacket with black and pink skirt

Long skirts

Long skirts tend to hang loose from the body, so pair these with a tight sweater to add some shape to your figure. That said, you can go for a chic winter-boho look by pairing your long skirts with tunics instead. Throw on an oversized cardigan, and you’re good to go!

Casual Skirts

For most skirts that stop above the ankle, grab a pair of knee-high boots.  The primary exception is hi low skirts – you can certainly wear these with high boots, but ankle booties and chunky-heeled pumps create a more elegant, flattering line. Also, if you’re wearing ribbed or patterned tights underneath your skirt, a shorter boot will show off the interesting pattern.

Maxi Skirts

Wear maxi skirts in winter by pairing them with warm leggings and cute booties. You can even wear a pair of thermal long johns underneath – maxi skirts are long enough that they’ll be completely hidden.

Winter can be dreary, but your outfit doesn’t have to be. Wear your skirts year round by adding tights, leggings and an appropriate coat during the colder months.

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Published on Jan 10 2018

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