How to Survive Your First Winter If You’re a Cold Weather Virgin

Growing up in Virginia, a state that has pretty much every kind of weather I’ve had plenty of experience both with walking to class in twelve degrees and seeing schools close because snow is even mentioned in the forecast. But for many twenty something Southerners born and raised in states like Florida, Alabama, and Georgia who’ve since migrated north for jobs, they’re facing their first real winter. And they have no clue what to do. Fear not, the ladies at Literally, Darling are happy to share our expertise on how to survive the fiercest of winters.

Winter Clothes

Where to find cheap boots & coats?

  • This is a great website for finding never worn to slightly used name brand clothes at an extremely discounted price.
  • TJ Maxx and Marshalls: Look in the fall for the most variety and towards the end of winter for the best deals.
  • Target and Walmart: You’re not going to care about name brands when you’re freezing or there’s snow up to your knees.
  • Outlet Malls: Columbia and NorthFace both have great deals out their outlet malls where you can get great coats for $100 or less.

Best brands


Doc Martens

While they can be expensive initially, they are well worth the price. I’ve worn them everywhere from an outdoor concert in the summer to climbing a steep snow and ice covered hill. Their tread is exceptional (bonus points: they’re waterproof) and they are the most comfortable shoes for doing a lot of walking or standing once you’ve broken them in.

Sorel Snow Boots

These hold up through multiple seasons, and give you plenty of traction in snow or ice. Pick some with lots of lining for more warmth, and make sure they are higher than ankle length. You can find these at a lot of department stores or Amazon. I wouldn’t consider them super cheap but they’re worth the investment.

Leather Riding Boots

Invest in a great pair of leather riding boots with a rubber sole. Just because there’s not a foot of snow on the ground doesn’t mean it isn’t going to rain, sleet, snow or all three. Leather riding boots are easy to pair with any outfit, typically can be warmed up with socks, and are great if you’re commuting using public transportation for those rainy winter days.  

L.L. Bean Boots

You may need to get on the waiting list the summer before, but nothing will keep your feet warmer or dryer through the long cold months. These indestructible boots will last for decades and thanks to the Maine aesthetic making a comeback, you can look fashionable while still being entirely functional.

Hunter Boots

On their own, these boots can be a bit chilly, but you can get so many fun and fuzzy warm inserts that it will hardly matter. Whether you’re sloshing through the wet muck of the city and would like to protect your legs farther than your ankles, or taking the dog to the muddy park, these boots are perfect.


Lands End Pea Coat:

I’ve had this winter jacket since freshman year of college. It’s seen me through many a snowstorm. I love that it reach almost to my knees so I don’t have to worry about getting a wet/icy butt when I sit down somewhere. It also has amazing pockets and is big enough that I can layer up underneath for the really cold days.

London Fog Black Trench Coat:

My favorite thing about this jacket is its removable lining, which makes it perfect for a rainy or snowy day in any season. This jacket with its deep pockets and equally deep hood make walking through freezing rain a little less torturous.

Columbia Omni-Heat Coats:

These coats are the bomb, especially if you’re into any kind of outdoor sport which is huge in New York. These jackets have a reflective technology in them that reflects your body heat keeping you toasty. Bonus, they often come in double layers which basically makes them two jackets in one that you can wear together or separate.

What makes a good winter coat or boots?

Lined, insulated, and waterproof are your go-to features when shopping. Look for temperature ratings on coats.  Good boots have a good tread that will prevent you from slipping and will keep your feet dry. If you’re going to be splashing through a lot of puddles or wading through lots of snow, definitely get boots that reach at least mid-calf.

What kind of coat (peacoat, hooded, long, insulated, waterproof)

For Iowa winters, or any winter where you’ll face both windchill and snow, definitely look for long, hooded, insulated and waterproof. Get a down or down alternative coat. Don’t worry about being cute. If it feels like you’re wrapping yourself in a down comforter, you’re on the right track. I highly recommended Lands End for their durability and warmth. Note: they do make cute down coats. Check TJ Maxx or Marshalls. But you will be too cold to care.

The wind in New York can be bitter in the winter so I definitely suggest opting for a longer coat in the winter than you may normally. Any type of coat that has technology meant to keep you warm and dry are going to be your best bets for surviving New York winters. Long black down coats are a popular choice. Throw fashion pretty much to the wind here because it’s honestly all about survival once winter rolls around.

Walking & Driving in the Snow

Keep an extra coat in the car. If your car breaks down in the winter, you’ll stay cozy warm. Also keep some kitty litter in the trunk of the car.  If you’re stuck on the ice, it’ll give you some traction. (I have recently become aware fancy people carry actual ice melt and sand, but you know – Vermont college kids carried kitty litter.)

Invest in a nice windshield brush/ice scraper and keep it handy (not in your trunk). It makes the snow clearing and defrosting process so much easier and you won’t be one of those idiots driving around with chunks of snow flying off their car roof.

Make sure you have a car emergency kit including flares, jumper cables, a space blanket, food, etc. It’s a good idea to have a blanket and an extra coat and gloves handy too. Even snow pants are a good call. Also, assume nobody around you knows how to drive in snow and that everyone will drive like an idiot. So use caution and take things slow when you need to.

Always err on the side of caution. My motto when it comes to the winter in New York is this: If there’s a chance I may not make it home from work or wherever I’m supposed to be going that day, I stay home. Make sure you pay close attention to your local radio stations and weather forecasts. Also become very familiar with your work’s policy when it comes to snow. If there’s a chance there might be a snow storm coming your way, don’t wait until the last minute to stock up on essentials.

Other Things You Probably Didn’t Realize About Winter

  • Always undo/take off/unzip some of your layers when you step inside, even if it’s at a store. Your body will adjust to the heat from those layers when you’re inside and they won’t feel as warm when you step back outside.
  • Wind chill. You’re like oh it’s not going to be that bad temperature-wise but then they mention a wind chill that’s cold as shit and you realize that every gust of wind is going to make you think you’re in Antarctica so nevermind.  
  • People suck at driving in the snow. Seriously, always assume people are going to not know what they’re doing when it snows because that’s how you stay safe. Getting horns honked at you for going too slow? Who cares? Better safe than sorry.
  • Make sure you shovel all the snow off your steps, front walk, driveway, and sidewalk. Anything left with turn to a thin sheet of ice and be way worse than the actual snow.

Is it vital to have waterproof footwear?

YES. I dunno about everywhere else, but Vermont had “mud season” which is an unofficial part of winter and is as wet as it sounds. -The last thing you want is for your feet to get wet and then be freezing cold at your desk or cubicle the rest of the day. If it isn’t snowing in New York, there’s a good chance it’s either raining sideways or sleeting so waterproof boots are a must.T here is nothing worse than walking around in icy, wet socks. Your feet, especially your toes, will thank you!

Do bulky sweaters/coats/outerwear made from wool or fleece or cotton as warm as something thin and light (but synthetically made)?

I am such a fan of wool sweaters and they will definitely keep you warm. In my experience, wool fleece and cotton do a lot better at blocking out wind than thin and lightweight materials.

Hat or scarf?

Hat usually, scarf for only the times when it’s snowing hard or aggressively cold. But opinions do differ, Sarah swears by scarves, “Keeps my neck cozy warm and I like that you can leave the scarf on indoors in like an office setting whereas it might be weird to leave a hat on.”

Allie loves the fleece infinity scarves from Old Navy. They keep you surprisingly warm and they’re cheap. “I always wear a hat or fleece ear cover too. Wool is itchy so I’ve never tried it but fleece is great for layering.”

Of course, both is always an option too.

Gloves or mittens?

Fingerless gloves that you can turn into mittens are the best as you can’t text/use your phone with regular gloves.Or invest in fleece tech gloves. I get mine at Costco. No shame.

Do you prefer to layer or to have a single coat?

Virginia’s all-four-seasons-in-a-week weather has made me all about layers. If the temperature is going to change a lot over the course of the day, definitely go with layers for optimum comfort. Besides layers, particularly insulated/cozy leggings are a go-to.That way I can wear skirts and dresses without freezing my kneecaps off.

Besides, if you’re cold all the time but don’t want to wear the bulky coat indoors, you can layer up in winter so you’re always cozy.

In New York, you pretty much have to be a layering master. That’s why I like vests. Vests add an extra layer of warmth for when you’re wearing your coat and when you’re not.

Contributors: Darrian, Sarah, Allie, Maggie, Katie

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