Five Fashion Experts Share Their Tips on How to Wear Winter Dresses

Many of us are seeing chillier temperatures on our weather apps. This almost prompts us to begin putting together our winter wardrobe. You don’t need to overhaul your entire closet. You can still use your favorite warm staples, such as sweaters and cardigans.

You can wear winter dresses, so don’t forget to pack them.

We don’t just mean sweater dresses. Your LBD is yours to wear, whether it’s minis, maxis or midis. It is a matter of how you style them in frigid weather.

Interview with InStyle: Celebrity stylist Cindy Conroy said that dresses could make for a great winter outfit. She adds, “I wear them almost every day of the year.”

Conroy states that dresses can be worn in winter without being too out of season or freezing. Consider outerwear, footwear, jewelry.

We have some tips to help you dress for the season. We reached out to five stylists to get their top tips.

Layer up

Ramy Brook Sharp, CEO of Ramy Brook and creative director, said that layering is the key to wearing a winter dress.

She tells Style that you can still wear your sleeveless summer dress, but layer it with something underneath. You can choose a button-down blouse or a turtleneck. A great leather jacket will last you through winter. You can wear it as part of your winter outfit, or you can take it off to coat check.

The Dress Can Be Used As A Blank Canvas

Mickey Freeman, a celebrity stylist, suggests that you build on it by adding outerwear and accessories to transform the look. His motto is: His motto? Maximum impact with minimum effort.

For example, I would wear a long-sleeved mini dress over a faux fox fur or feather scarf to create an evening look. For instant glamour, pair with a metallic or embellished box clutch and add high-heeled boots to complete the look.

Take care of your footwear.

Conroy recommends styling a dress with thin fabric with ankle boots between 4-6 inches in height (as long you are comfortable walking in them).

“Those extra inches of material will protect your legs and ankles from the freezing cold and snow piles mysteriously sneaking in to your boot.”

Choose a Puffer Vest Over Traditional Outerwear

Puffer vests have been growing in popularity on social media (like this H&M quilted number). You can find them in many lengths and styles. Freeman says they make a unique combination with a dress.

He tells InStyle that they “stylistically juxtapose each other.” The puffer vest still has a utilitarian feel, but the lack of sleeves helps to keep the dress’s form visible.

Choose Long Coats Over Cropped Styles

It’s not easy to stay warm when temperatures dip below freezing. Conroy reminds you that long outerwear is the best choice for dressing up.

She says that long coats made from wool, cashmere, faux fur, shearling or faux fur are your best friends for keeping warm. The additional fabric acts as a barrier to prevent the winter chill from getting in. Even wearing a small dress, the coat will wrap around your legs to keep the cold out.

Get Punk

Thanks to Kourtney Kim and Megan Fox, all things punk rocker will be ‘in’ in the future. Freeman believes this is a great way to find winter dresses.

She says, “I would wear a form-fitting mindress underneath an oversized leather motorcycle jacket, a distressed, oversized chunky knit scarf, high combat boots and Wolford fishnets for a splashes of punk rebelliousness.”

For an ’80s flair, add shoulder pads.

Although ’90s grunge is timeless, JLUX cofounders Teresa Jaide and Christina Jaide tell InStyle that they are taking inspiration from the ’80s for styling dresses this winter.

Christina tells us that cold weather is upon us, and she loves finding creative ways to update our favorite dresses while still staying warm in the new season. Shoulder pads are a favorite style tip. This simple trick works best when worn with a sweater or knit dress, as it lacks structure.

Teresa recommends that you add warmth to your legs, which is where you most need it.

This look is perfect for winter! Layer up with boots over the knees and a long coat.


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