Styling Winter’s Top Fashion Trends Made Me Fall Back In Love With Dressing Up

Gisele Smith
Styling Winter’s Top Fashion Trends Made Me Fall Back In Love With Dressing Up
Photo: Courtesy of Gisele Smith.

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It’s finally time to discuss winter fashion trendsIt’s no secret that 2020 has been extremely out of the ordinary, and like many others, I’ve spent more time in sweatpants and leggings than I would have ever expected (or liked) to do. If you know anything about me, I always get dressed up.

Putting on a full outfit is my comfort zone, and at the beginning of quarantine, I did just that. I wore my elaborate spring and summer dresses just to work from home and sit on Zoom calls all day, but heyat least I looked good as the world felt like it was crumbling around me. 

I did this for a while, months even, until one day I hit a wall. Any enthusiasm I had in regards to styling myself went out the window, and biker shorts and sweats became my new best friends. I found myself rejecting my usual style because it reminded me too much of the way things used to be, and I just didn’t feel like that person anymore. So much around me was changing, and as I changed, so did the way I wanted to dress.

It’s funny to think about just how much what we wear seeps into our culture, and this year couldn’t be a better example. As the world changed around us, so does the fashion industry. It has had to adapt, and while some thought the last few months would mark the death of fashion as we knew it, I’d argue that quite the opposite has happened—fashion has been given a breath of new life. 

Some thought that the last few months would mark the death of fashion as we knew it, but fashion has been given a breath of new life.

Fashion’s biggest players have had to step it up, whether that be through inclusive or sustainable practices, or just sparking a jolt of creativity to get us excited about clothes again. With winter upon us, I, just like the industry itself, am ready to embrace what’s new. 

This season, there’s a new guard of style stars setting the trends and holding other industry players to higher standards—and of course, I wanted the inside scoop. For that, I went directly to Telsha Anderson, owner of and buyer for New York concept store T.A.

The way Anderson approaches her store, which opened at the start of the pandemic, is with aim to “reflect women of all sizes and colors.” The current pandemic and blizzard of racial injustice haven’t halted her; in fact, they’re inspired her to push onward. With an intentional focus on POC designers, Anderson has declared that when it comes to representation, she’s “not doing it if they’re not in it.”

When I picked her brain regarding the top winter trends for 2020 into 2021, Anderson was confident and unapologetic in her declarations. After chatting with her and putting my mind (and wardrobe) to the test, I styled myself using her advice, and my excitement about getting dressed up has been fully restored.

Below, a look at Anderson’s trend predictions, and how I made them work for my own personal style.

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STYLECASTER | Winter Fashion Trends

Courtesy of Gisele Smith.

Ready or Knit

This one might seem obvious, but Anderson notes that it’s all about finding more unique sweaters to help you stand out. “Knits are perfect for winter layering” says Anderson. “This knit is my personal favorite because there is no back to it. You can wear it with an overcoat and still feel warm”. If you prefer a one-piece look, she adds: “Also, Ribbed knit dresses, perfect for this season as well.” 

Usually, I style my knits with jeans, so I decided to switch things up and take Anderson’s advice. I paired a short sleeve knit over a dress and styled the pieces with a blazer and boots for the perfect layered look that stands out from the crowd. My biggest takeaway? Don’t be afraid to shop the men’s sectionthis no-sleeve knit was perfectly oversized for layering over my dress, and in my opinion, all clothing is genderless.

STYLECASTER | Winter Fashion Trends

Courtesy of Gisele Smith.

On Mute

Minimalists and neutrals-lovers, rejoice! “Muted colors are definitely a fall trend. Browns especially,” says Anderson. “When worn as a coat, it’s something you can throw on that still makes its own statement within whatever you’re wearing.” 

For this look I decided to step out of my patterned-filled comfort zone and go full monochromatic with matching socks, pants, top and unbuttoned shirt, and just my black shoes for some contrast. What I love so much about taking inspiration and advice from others is that it challenges you to think outside of the box, and this was a hit! For this trend, think Yeezy vibes, but make it unproblematic.

STYLECASTER | Winter Fashion Trends

Courtesy of Gisele Smith.

Keep It Cord-ial

“In my opinion, Corduroy is never going to die”, says Anderson, and I couldn’t agree more. Whether it’s a jacket or a pair of pants, it’s the perfect way to add a pop of texture while transitioning your wardrobe for colder temperatures.

That said, don’t say goodbye to your favorite summer dress just yet. I threw a corduroy jacket over one of my fave summer go-tos and it was the perfect way to transition my pieces and save some coins in the process. To make it extra winter-appropriate, I threw on a printed mesh shirt underneath for added warmth and (of course) my classic pattern-clashing signature touch.

STYLECASTER | Winter Fashion Trends

Courtesy of Gisele Smith.

Printed Denim

I love my basic denim, but Anderson makes the case for amping up the pattern this season, and she’s won me over. “I love to fill the store with things that will carry over easily from season to season. Something indicative of this trend is printed denim,” says Anderson. “Denim is going to continue to be huge.” 

Now as someone who is a recent denim convert, my collection is slowly growing. While I didn’t have any printed denim on hand, I added that implied boldness through a printed sweater and a large denim jacket with sherpa detailing for contrast. This printed pair is definitely next on my list, though! This is a great reminder that following trends is not about spending lots of money to recreate them exactlyit’s about using them as #inspo and making them work for you!

STYLECASTER | Winter Fashion Trends

Courtesy of Gisele Smith.

The It Bag

Statement bags are in, so justify buying something unique and you won’t regret it. Promise! “Slingback bags like this one are going nowhere,” says Anderson. “I wear mine over big coats.”  

Now, I am a self proclaimed bag lady. If there is any place in my wardrobe I will splurge, it’s on a nice, quality bag. I personally love a statement bag in the black or white color family, like my pick above and this similar yin yang piece by Paloma Wool. It is the perfect bold touch that’s still versatile enough to go with many outfits, making it worth the money in the long run!

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