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The 2019 Winter Wardrobe Essentials I Wear Over And Over Again

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Don't judge me too much for bringing this up, but I'm a Capricorn. I'm pragmatic, practical, and serious. And though we're in the prime time of year to celebrate me (my birthday was in late December), it's also the time of year I find to be my biggest challenge in terms of energy and creativity. Being the basics-loving woman that I am, diverting my focus to think about layering trends in a coordinated way can send me into a spin in the morning (especially when I'm trying to get dressed before the sun is even up). Which is why I've come to rely steadily on what I'll lovingly refer to as my "starter pack," a collection of stylish winter wardrobe essentials for 2019 I know that I can mix and match without taking up too much brain power.

While when it comes to personal style there will always be extremists, it's safe to assume that myself and most others fall somewhere in the middle of the fashion spectrum. We respect Mari Kondo, but our drawers still runneth-over sometimes. We love a pop of color or a fresh print to try, but we draw the line at anything that verges on cartoon territory. That's why curating a list of trustworthy winter pieces has been my saving grace. By combining a few key trends with more classic staples I've put my analytical skills to use in a sartorial sense.

Despite my admission that creative layering doesn't always come naturally to me, I've found that the key to appearing put-together December through April is about being able to stack pieces one on top of another in a way that feels more purposeful than happenstance. Below, I've outlined 11 key items I turn to, all of which can be easily mixed and matched to create more outfits than I can count (sorry, I'm leaving the math to someone else). Now, find your winter starter pack below.

@aemiliafay

Polished Trousers

Let's kick things off by focusing on workwear staples. While I'm typically a jeans girl, I've found that a comfortable trouser is actually better suited to winter months. If it's super cold, I can easily slide Uniqlo's Heattech leggings underneath, and a loose wool pair feels more like wearing pajamas out than anything short of sweats.

Belted Tapered Pants

$640

Victoria, Victoria Beckham

Blazer-Coat Hybrid

The great thing about a strong pair of trousers is that ideally they'll work just as easily with a sweatshirt and sneakers as they will with pumps and a crisp button-down. One way I've been styling my bottoms on repeat during the week is with a heavy blazer-coat hybrid. For days when it's not puffer-level chilly, I find a well-tailored coat to be an ideal layering piece that works for both in the office and when I run out for lunch.

Gemina Blazer

$1,195

$597

Joseph

Under-Outer Layers

As I mentioned above, Heattech has also become a saving grace for me during winter months. I spent my first few east coast winters without it, and the second I finally sprung for some, I noticed the immediate difference. Uniqlo's recent collaboration with Alexander Wang is a current favorite because though it's meant to be worn layered under everyday clothes, it's cute enough to wear on its own.

Heattech Body Suit

$40

Uniqlo x Alexander Wang

@aemiliafay

Now, for those days when a medium-warmth coat just won't cut it, I recommend breaking out the big guns - a heavy duty puffer (I prefer Aritzia's Nano Puff or anything from Patagonia), or a current favorite of mine: an impenetrable teddy bear coat.

Teddy Coat

Koda Coat

$1,295

The Arrivals

Wide-Leg Denim

As for denim, during the winter I try to avoid anything with too much stretch (it doesn't protect against wind very well), and aim for looser fits in case I want to layer something warm underneath. Vintage-inspired high-rise jeans are cool, but also feel office appropriate.

A Straight Leg Jean

$295

Goldsign

Practical-Chic Shoes

As for footwear, I basically oscillate between two things: a sturdy pair of lug-thick-soled boots, and sneakers. While obviously, something sleeker is needed for when I have to dress up (I promise I don't wear sneakers to anything where the invite specifies black tie), the vast majority of the time, something slip-proof, that has a little extra platform between me and the frozen sidewalks of New York is the ideal choice.

Fara Boots

$1,390

The Row

Temper Run Sneakers

$140

Adidas

@aemiliafay

As a realistic earth sign, I try to keep getting dressed as easy (and comfortable) as possible on the days I'd rather not leave the house. Which is why I take every opportunity I can to wear athleisure staples like leggings, sot knits, and cozy-cool sweatshirts. Those three items make up the key parts of my weekend uniform, when I know I'll be mostly taking it easy.

Comfy Leggings

I have more leggings than I'd readily like to admit, but I find that I like different brands and styles depending on what my day entails. For the gym I like Nike's tech sweat, for hiking I'm a fan of Outdoor Voices, and for errands I usually opt for leggings that have a fashion twist, like this logo style from Paco Rabanne. If I'm just watching reruns of The Office in bed, I'll take any of the above.

Bodyline Leggings

$218

Paco Rabanne

Sweatshirt or Sweater

I alternate between hooded sweatshirts (added head warmth) and oversized knits (like leaving the house in a blanket), and though these are both staples for the weekend, I usually find ways to dress them up for the office too.

Jane Hoodie

$150

Kith

Carlito Sweater

$1,350

Khaite

Statement Accessories

Lastly, to finish off my wintery ensembles, I also find that accessories are a great way to make staples feel fresh. Layer on scarves, beanies, and even barrettes and headbands to amp up your cold-weather look.

Pansy Face Appliqued Ribbed Wool Beanie

$145

Acne Studios