12 Tips to Winter Dressing (Or How To Look Cute When It’s Cold AF)

As January draws to a close, and the long cold month of February stretches out before me, I long for the hibernation station of my couch and blankets. Unfortunately, most days I have to throw on some version of real clothing and venture out into the grey haze that is Winter. It’s bleak, but winter dressing doesn’t have to be a drag.

Here are my 12 tips and must-haves to survive the coldest months of the year in style and warmth.

12 Tips for Winter Dressing

1. Longline Wool Coats in Neutral Shades

Longline Camel Coat
Photo Credit: Death By Elocution

You need at least one of these. Obviously, it’s winter – you know you need a coat. And although parkas and leather jackets have their place, I find that nothing beats a long, thick, wool coat in a neutral shade. Its length keeps your lower body warm and the quality fabric and clean lines will add polish to your scruffiest winter outfits.

Yes, I’ve thrown a longline wool coat over leggings and a sweatshirt to the grocery store – and ya know what? It effing works. Color-wise, I recommend black as a staple and medium-camel brown as a lighter option. Camel coats are having a moment right now but have actually been in style for ages. It’s a classic shade and cut that will last you for years.

2. Black Ankle Boots with a Block Heel
Topshop May Boots

Topshop May Boots On Sale $90

Some girls rock sneakers or slip-ons all season long – with their skinny ankles and long legs (ahem, Kendall Jenner). For my own, more average body type, I’ve found that I get the most wear out of a pair of simple, black ankle boots with a small 2-inch block heel. The heel is just tall enough to be flattering but low enough to be comfortable. The black color makes it versatile and easy to throw on with any outfit.

I purchased the Topshop May Sock Boots in the fall of last year and have already gotten my money’s worth. I wear them almost every day and will probably continue to do so through the rainy month of April.

Sock boots are super on-trend right now, but if that’s not your deal, you can also check out a chunkier twist on the combat boot like these babies from Zara. These are a great option if you’re dealing with icy sidewalks and slippery surfaces.

3. Black High-Waisted Skinny Jeans
Topshop Jamie Jeans

Topshop Jamie Jeans $70

I mean, these are a staple year-round but especially during Winter when most skirts and dresses are just out of the question. The high waist and dark color is flattering on all body types and serves as a great starting point for any outfit.

Dress them up for a night out or dress them down for your errand-running needs. I even wear these to work since my office is pretty casual. Regardless, if you don’t own a pair of high-waisted black skinny jeans, this purchase might just change your fashion game.

4. Oversized Sweaters
Gigi Hadid Oversized Sweater

Gigi Hadid rocking an oversized sweater

Tis the season for layering! Stock up on snuggly, soft sweaters in versatile shades like grey, black, and cream. The neutral color palette ensures you’ll be able to pile them on top of any other outfit you own without worrying too much about matching.

Watch out for anything too itchy and buy them in a larger size so you can layer them on top of flannels and t-shirts. I like to buy these sweaters in one of two extremes – either long enough to partially cover my bum or short and cropped to pair with high-waisted styles.

5. At least 1 flannel shirt

Flannel Shirt Outfit

For more casual days, you can’t go wrong with a lumberjack-inspired, plaid, flannel shirt. These have been in for years and probably won’t be going out of style anytime soon. I like them in either a dark green and navy plaid or a bolder red/plum plaid.

I like styling them with a topknot or beanie, leggings, thick socks and chunky boots. They also go great with oversized sweaters or tied around the waist 90s grunge-style.

6. Beanies
Zara Cat Beanie


Nothing worse than cold, red ears when you’re waiting for the bus or metro. Protect your head from the cold with a snuggly, knit beanie that covers your ears. I love the ones I’ve been seeing in stores lately with pom poms or kitty ears. Regardless of what your style is, these hats are a must-have for my winter wardrobe. My mom says that if your head is warm, then the rest of you will be warm too. Wise words, mom. Wise words.

7. Large scarves in neutral shades
Oversized Winter Scarf

Photo Credit: Lou What Wear

Are you sick of the phrase “neutral shades” yet? Be patient, Paduan. Oversized, chunky scarves are a staple of Scandinavian dressing for good reason. They’ll protect you from the blistering wind and add a level of panache to an otherwise basic winter outfit.

Although you can certainly get these in some cool colors or patterns, starting your collection with a solid grey or camel color will ensure you get the most bang for your buck.

8. Black leggings
Asos Leather Look Leggings

Asos Leather Look Leggings $35

As if I even needed to list this one…most of you probably already have a pair of black leggings in your wardrobe. These are my go-to for snow days at home, or if I have to run out real quick to replenish my Ben & Jerry’s supply.

I’d also recommend experimenting with different textures like faux leather or crushed velvet. I’ve had this leather pair from Asos for a couple years now and have gotten so much wear out of them. They’re great for going out to dinner when you know you’re going to eat more than your high-waisted black skinny jeans will allow.

9. Snow Boots

If you live in an area with lots of snowy weather, then the sleek black sock boots above probably won’t cut it. I’m leaving this one pretty vague since it depends on your style and what kind of whether you’re dealing with but here are some great options:

Combat Boots (my favorite)

Steve Madden Combat Boots

Steve Madden  $79.95

L.L. Bean Boots (a classic)

LL Bean Boots

LL Bean $129, Photo Credit Kelly In The City

Hunter Rain Boots (great for rainier climates)

Hunter Rain Boots

Hunter Rain Boots $109.99

10. A-Line Skirts or Dresses with Tights

Winter Skirt Outfit

This isn’t exactly the season for skirts or dresses but when the occasion calls for it, or when you get sick of your skinny jeans, these styles can be worn with some thick black tights. I like black circle skirts or suede A-line skirts with tights and ankle boots.

Dresses can be a little trickier but a slim-fitting pencil dress can easily be paired with black tights and closed-toe pumps for fancier occasions.

11. Black leather jacket
Zara Faux Leather Jacket

Zara Faux Leather Jacket $69.90

If the deep freeze breaks and the temperature reaches above the freezing mark – I like to reach for my Zara leather jacket. I’ve had this one for a few years and have gotten so much wear out of it. It’s a staple for in-between season dressing, as well as for warmer winter days. I bought mine in a small but would advise anyone else to size up so you can wear it over your chunky sweaters and oversized flannels.

12. Statement Pieces
Statement Winter Dressing

Photo Credit: Claudia via Lookbook.nu

Knits in bold colors, a leopard print coat, a bright lipstick, or fun tassel earrings will go a long way to brighten a cold, grey day.

Okay, now that I’ve said “neutral shades” 3 times… I’m gonna tell you to embrace color. It’s important to invest in your foundation pieces as neutral building blocks to your wardrobe. But once you’ve got that down, it’s great to play with color – especially as a contrast to the grey, wintery backdrop.

I love to wear a cherry red lipstick (obvs), fun tassel earrings, or a bold blue sweater to brighten up my otherwise neutral outfit.

And there we have it! 12 tips and must-haves to make winter dressing easy. What are your most-worn items this season? Did I miss any? Comment below with your favorite, cozy winter wears!


    • Anna Christine
      February 15, 2018 / 4:34 pm

      Thanks girl!

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