How to Dress for Winter (Plain and Simple)

by Bailey Powell

Layering is intimidating because the more wardrobe components involved, the easier it is to mess up an outfit. While some people are born with an innate sense of style, effortlessly pulling together looks and piling on perfect accessories no matter what the season, some people are not. I honestly fall into the latter category and particularly struggle to create fun, fresh looks for the colder months. Since getting dressed should always be a joy, I’ve created these sets to inspire ideas for those of you who might also need a mid-winter sartorial pick-me-up.

Wear your short-sleeved favorites into winter by layering them over a turtleneck. Tie back in the brown from the blouse with a scrunched up pair of elbow-length gloves, keep your feet warm with shearling-lined boots, and add a pop of color with a happy shade of nail polish.

Wear statement shoes (those Lisa Frank-esque Steve Maddens are on sale for $42, swoon) with plain over-the-knee socks and a chic shift dress in order to avoid looking over the top. Repeat the purple with a thin belt and finish the look with some sleek earrings.

Incorporate winter white with a dramatic cape, gloves, and bag. Keep the rest of the look light with khaki cords and gold accessories and let the striking red lipstick be the icing on the cake.

Be match-y with a ladylike wrap dress and velvet pumps in the same hue. Paint your nails bordeaux for a beautiful contrast and wear nude tights to keep your legs covered. Top it all off with a fabulous faux fur coat and a trendy bronze clutch.

Look statuesque in a maxi skirt and keep your legs warm underneath with a pair of tights and low-heeled wedge boots. Wear a statement necklace that makes a clinking noise your grandchildren will remember(!) over a neutral turtleneck and keep a faux fur vest handy in case you get cold. Pull the outfit together with a whimsical yet sophisticated striped bag.

Go for a mod look in a mint coat and try some charcoal pieces instead of all basic black. Capitalize on the snakeskin trend with a neutral bag and keep the whole look fresh with pretty pink lips.

Cobalt is still going strong, so incorporate it with a tailored jacket worn with a modest pencil skirt. If you’re feeling saucy go for the bordeaux hosiery, but classic black with a back seam is fool-proof. Tie the white from the jacket back in the with pointy-toed flats and wear Isabella Blow sunglasses + studded gloves for glamourous eccentric bonus points.

Wear a cozy ruana/cape over plain black trousers and add an inch or two with some slingback kitten heels. Keep the rest of your arms covered with some long leather gloves and look undeniably feminine with red nails and cat eye sunglasses.

Now go forth and be chic, winter warriors!



Some of the things shown are high-dollar and some are surprisingly inexpensive, but the main point of this post is to show you how to wear a look opposed to what exact things to buy. However, if you’re interested in where to find a specific piece simply click inside the age group and you will be whisked away to it’s actual Polyvore page complete with an inventory of everything shown.