This past weekend, many looked outside their window to see flurries and snowflakes dotting the sky. And with Thanksgiving nearing and holiday sales launching, it prompts the debate: When can we officially start celebrating the holidays?
Before you pull out the Christmas tree, consider stocking up on must-have basics and elevated styles for your winter wardrobe first. To help you get started, stylist and on-air expert Jasmine Snow shares approved finds on Jenna & Friends from brands you know and love (and most likely shop on the daily), including Target, Old Navy, and more.
From a "one-and-done" dress that can be worn both in the office and out for festive gatherings, to cozy sweaters that you can bundle up with during your next holiday movie marathon, we have trendy seasonal finds starting at $20.
Winter style staples seen on Jenna & Friends
For cozy winter errands
A cozy fleece sweater is paramount to any wardrobe, especially a winter wardrobe. This under-$50 option is available in 10 different colors, including neutrals and earthy shades such as army and dark green.
"It’s also a great length for leggings or joggers so you get a relaxed athleisure vibe without looking sloppy," says Snow.

"I was actually surprised by how much I liked these," admits associate editor Kamari Stewart. "They have a 'satiny' feel to them and are both soft and stretchy. I wore these on a flight and on public transit [and] walking to my hotel, and I was comfortable enough to keep wearing them for the rest of the day if I had to. The pockets are decently deep, too, so I wasn't worried about things falling out while I was on the move."
Other editors described them as a nice "lightweight, multipurpose" pant, having worn them on travel days, to the gym and more.
Everyday basics
Black long sleeves are wardrobe staples for a reason! They allow you to continue wearing the tank tops and short sleeves you love for warmer weather, or can be worn solo with a patterned skirt or pair of pants.
"The fabric is super soft and stretchy, so you get that smooth, body-skimming fit that’s really flattering," says Snow.
We're big fans of Halara here at Shop TODAY, with editors describing their jeans as among the most comfortable pairs they've owned. This option proves to be no different, with reviewers raving about the comfort and versatility, as they're able to dress them up or down depending on the occasion.

The one-and-done winter dress
Snow says this piece can truly take you from day to night — from the office holiday party to hosting your own. "It’s incredibly comfortable but still polished," she says. "The Jersey fabric has stretch, so it will skim the body and highlight your curves in all the right places."
It's part of Old Navy's "The Occasion" line, which provides shoppers with more elevated attire to wear to weddings, dinner parties and more.

Accessories for the season
"A clean, minimal design like this defines the waist on dresses and sweaters or a high waist pair of jeans," says Snow, adding that "if you’re not big on lots of jewelry, this belt will add just a hint of shine without overwhelming the whole outfit."
"This soft structure makes the look casual but still chic, so you can easily wear it dressed up or down," says Snow. It gives a luxe look for less, as it's only $30.

More winter style staples to shop
Stay extra warm in your favorite sweater dresses this season with a pair of fleece-lined tights. One Shop TODAY writer said, " I was worried they would be too warm, but somehow the fleece is just cozy enough without making me overheat."
A simple beanie that goes with any winter outfit is a must for the season. This bestselling option from Carhartt is unisex and comes in tons of colors to choose from.
Clogs are a trending topic each fall — they combine what we love about sandals in the warmer months with a closed-toe option for the winter. And we're not the only ones, podiatrists love them due to their supportive structure, wide toe box, "anti-fatigue footbeds" and more.
A puffer vest is the perfect layering piece to keep warm during the winter months. You can wear it with a long-sleeve tee, or pack it under a heavy coat for blustery days.
Slouchy, relaxed and comfortable — these jeans are well-loved by reviewers for their soft, high-quality material and baggy silhouette. They're also tall girl-approved, with many reviewers appreciating the wide leg style and longer length.
If leopard print is your favorite style (or you love a patterned pump), this affordable pair easily matches any holiday dress you're planning on wearing. They're also available in a brown and white dotted pattern and a deep brown color — in case your skirt or shirt steals the show.
Experts we previously interviewed said it's important to prioritize white sneakers that have a different-colored outsole — so they don't get, or appear as dirty. These sneakers have a tan, textured sole that grips the ground as you walk, preventing slips and trips.
Meanwhile, there's a memory foam insole keeping your feet comfortable and supported from the inside.
If you've been nervous to try stilettos because you're afraid of slips and trips, this pair has a slingback attachment that helps feet remain secure and in place.
"I have been counting down the days until it's cold enough to wear this sweater, and today is the day," says production associate, Audrey Ekman. "I'm happy to report it's every bit as cozy as I was hoping it'd be, as a cotton-cashmere blend. I layered it over a long-sleeved base layer and it didn't look bulky or bunch up at all, plus it stays tucked in thanks to the bodysuit bottom. Such a great staple piece for fall and winter that I'm excited to style with jeans, skirts, slacks, cardigans and more."
Reviewers describe this pullover as "exceptional," with its soft, quality fleece fabric and half-zip style being easy to slip on and off. It's ideal for running errands quickly or cozying up at home.
A pair of tall boots is the perfect thing to slip over leggings or tights during the wintertime, to pair with your favorite sweater or dress.
This specific pair earned high praise from social media editorial assistant, Annie Shigo, who compliments how easy they are to take on and off.
Bundling up for the snow never looked so good. This twill jacket is crafted out of a cozy polyester fabric that promises to keep you warm.
Associate editor Shannon Garlin initially purchased this top to remain warm on a skiing trip, further finding that its lightweight fit and feel let her move without restriction.
"But the most notable feature was the promised moisture-wicking fabric," she says. "We skied to a restaurant, and when I peeled off my ski coat and sweater, the underlayer felt dry and my sweat was absorbed."
Vuori is a Shop TODAY editor-loved brand, with writer Emma Stessman naming this hoodie as one of her go-tos for keeping her warm on long winter walks.
"I had been hearing so many great things about Vuori over the last year and when the brand sent me a few pieces to try, I finally understood why," she says. "I particularly loved this hoodie, which has gotten me multiple compliments from friends. It is so soft and cozy and pretty stylish, too. I love the slightly cropped fit and quarter-zip design."
Meet the experts
Our team features a range of qualified experts and contributors in our broadcast segments to reveal the latest in trends, remarkable sale events and all things shopping across a variety of categories. Products were independently chosen by members of the Shop TODAY team along with Jasmine Snow.
- Jasmine Snow is a stylist, on-air fashion expert and editor.
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How we chose
The Shop TODAY editors and writers search the internet to find the best products out there. We interview expert sources, comb through customer reviews and even use our own personal experiences to make shopping easier for our readers.
As an editorial team, we independently create content and determine coverage based on research, reporting and what we think TODAY.com readers would like to read about. The goal of our content is to provide a service and inform readers who are on the hunt for the latest products to help make their life better. Items are sold by retailer, not TODAY. Pricing and availability are accurate as of publish time. Learn more about Shop TODAY.



























