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Ask anybody and they’ll tell you fall is the best season for dressing.
Summer’s too hot and winter’s too dark and dreary, but fall is that sweet spot where you can actually have fun with fashion. That said, what’s a girl to do when we hit the tail end of fall—when it’s plenty cold out, but not quite “bundle-up-in-a-parka” weather? I have two words for you: smart layering.
In fall, layering is an art form. It’s your chance to take your favorite warm-weather pieces and make them work for cooler temps. Maybe it’s adding a turtleneck and tights to the slip dress you wore all summer, and suddenly you’re got a chic (and cozy) new look. Or try a white button-down layered under a chunky knit with jeans and loafers for a put-together ‘fit.
To make things easy for you, we’ve rounded up eight key pieces (all under $50) that’ll help you nail that tricky transition from fall to winter. Get ready to stay warm and look good, no matter what the forecast says!
Nordstrom Cotton Blend Button‑Front Sweater Vest ($33.39)
If there’s one piece that screams fall layering essential, it’s a sweater vest like this. The chunky knit adds just the right amount of warmth for chilly mornings, while the sleeveless silhouette keeps you from overheating in the sun.
I love that it’s versatile enough to wear now and later. For those in-between fall days, try layering it over a white button-down with relaxed jeans and loafers. (You’ll get minimal bulk, and still look put-together.) As temps drop, swap the shirt for a fitted turtleneck, add wide-leg trousers or a midi skirt, and finish with ankle boots.
BP. Oversize Cozy V‑Neck Sweater ($49.50)
What’s better than finding a cute, cozy sweater? Knowing exactly how to style it year-round.
This oversized V-neck version is plush and soft, with a deep neckline and relaxed silhouette that keeps it feeling stylish instead of sloppy. When the weather’s still mild, take your cues from the model and pair the sweater with a flirty skirt or mini. Once the temps dip lower, switch gears with pants or jeans, and don’t be afraid to add tights underneath for extra warmth.
Levi’s Ribcage High Waist Straight Leg Jeans ($41.16)
With its signature super-high rise and classic straight-leg fit, these Levi’s Ribcage Jeans define your waist and flatter practically everything in your closet.
On crisp (but not freezing) fall days, try them with a tucked-in tee and loafers or ankle boots. When winter really settles in, layer a slim turtleneck under a chunky sweater and finish with a wool coat. And don’t pack them away once it’s warm again! These jeans are breathable enough to wear on mild summer days, too.
Halogen Crewneck Long Sleeve T-Shirt ($22.99)
I love a long-sleeve tee because it’s the hero of any transitional wardrobe. The key is finding one that’s soft, fitted, and cute—and this one from Halogen checks all three boxes. Made from smooth, stretchy jersey, it’s lightweight yet cozy, with a flattering silhouette that layers well.
When it’s warmer out, wear it on its own with a midi skirt and ankle boots. Once it gets cold, make it your base layer under knits, blazers, or coats for extra warmth without the bulk. Trust me, you’ll be so glad you have it.
Open Edit Daydream Rib‑Lounge Pants ($49)
Who says transition dressing is only for when you leave the house? These ribbed lounge pants from Open Edit prove you can stay just as stylish while cozied up at home. The soft ribbed fabric and cropped, straight-leg fit are giving “cozy-luxe.”
Pair them with a fitted long-sleeve tee or a chunky cardigan for the ultimate WFH look. And if you do need to step out, just throw on sneakers and a wool coat.
Thread & Supply Hooded Fleece Shacket ($45-$49)
True story: I have an oversized jacket-slash-wrap that reminds me of this one. I got it ten years ago and still break it out every fall and winter. That’s because there’s just something great about an oversized fleece layer! It’s big enough to cozy up in, but still polished enough to wear out.
This hooded “shacket” finds the perfect middle ground with its plush polar-fleece fabric and drawstring hood. You can wear it as a standalone hero piece with jeans and ankle boots, or layer it over a slip dress for that high/low mix of cozy and chic. And come December, just add a thick scarf, swap in thermal tights, or layer a fitted long-sleeve tee underneath for extra warmth.
Halogen Open Front Longline Cardigan ($27.65)
This long, open-front cardigan is cotton-soft, with a flowy silhouette and side slits; plus, the front pockets are perfect for keeping your hands warm.
I love a cardigan for its possibilities. For example, you can wear it over a fitted long-sleeve tee and jeans for an easy, transitional look, or layer it over a dress for more of a boho vibe. Once it’s freezing outside, add scarves, chunky sweaters, or a coat on top. This could be the layer that makes all the difference in keeping you cozy!
New Balance RC42 Sneaker ($45.49)
Even when the weather turns gray and chilly, you don’t have to sacrifice style. These New Balance RC42 sneakers keep your look grounded and cool, with a low-top, vintage-inspired silhouette and minimal detailing that works with everything. The grippy gum-rubber sole also means you can easily handle snow, sleet, or wet sidewalks.
For transitional dressing, pair these sneakers with jeans and cozy socks that peek out just enough to show off a little personality. A structured beanie, scarf, or crossbody bag can elevate the look while keeping you warm, so even on chilly days you stay warm but look put-together.
Transitioning from fall to winter doesn’t have to mean sacrificing style for warmth (or vice versa). These eight essentials make it simple to mix, match, and layer so that your wardrobe feels fresh and functional, no matter what the weather brings.
