I don't know about you, but there's something about the first really cold day that makes me want to give up and pull on my stained, striped, wool sweater. But this year, I'm determined not to let the dropping temperatures get in the way of embracing life outside my apartment. Trip to the bodega? There's a patterned turtleneck for that. Solo date at the movies? No better time to button a cardigan up all the way and ask for extra butter on my popcorn. A great sweater is no small thing: Worn over a dress, it keeps things cool, and tied around the neck, it feels preppy without feeling too stuffy.
If you're in need of some major winter style inspiration, let this guide remind you of the magic of getting dressed in clothing that makes you happy, no matter the weather. Read on for 27 of the cheekiest winter sweaters to perk up even the dreariest of days.
Relaxed in fit, neutral without being boring, and downright cheerful, this Rails design will have you showing up to 9 a.m. meetings ready to roll.
Functionality at its chicest, this sweater from La Ligne is a dream for errands and weekend outings alike. It's fashionable without feeling too trendy, and the winter white cable knit is a reminder to enjoy all the best parts of the chilliest months.
If polos have integrated their way into your wardrobe, why not embrace the trend in sweater form? This pretty in pink look from Abercrombie & Fitch feels cool over a floral dress or layered with a tight turtleneck.
An outfit all on its own, this sweater is the missing item in your wardrobe. Paired with flared pants, it feels totally of the moment. Try it with a black skirt and tights if you're a little less keen on a '90s vibe.
This sweater is for the pattern clashers and colorful dressers. The houndstooth feels anything but old-fashioned in this vibrant rendition of the timeless pattern.
A certain remedy for winter blues, this cheerful green sweater is surprisingly versatile. Pair with the matching pants for a luxe lounging look, or take it outside with vintage Levis and a structured blazer.
This is the sweater for the sweater lover who's looking to invest in something special. A fashion editor favorite, the soft camel color and consciously luxe recycled cashmere fabric help this piece to elevate a cold-weather staple.
Roomy in just the right ways, this Spanish wool sweater is the epitome of cozy for seasons to come.
Embody sunshine on a cloudy day with this wool cardigan from Ganni. Try it buttoned up with your favorite jeans, or leave it open over a jumpsuit for days when you just want to get work done.
Keep things cozy while dressing up for your 9 to 5 in this spread collar style sweater. Made of 100% cashmere, it's super comfortable while feeling polished.
Essential for a reason, this sweater is the perfect place to start if you're looking to upgrade to cashmere. The midnight navy color is an ideal winter neutral.
Enjoy this puff-sleeved, cropped sweater for its comfortable, soft alpaca blend as well as its design, which adds whimsy to a classic black shade with colorful stripes and butterflies.
If you know you love a black turtleneck and are simply in the market to affirm your affection for the silhouette, look no further than this perfectly oversized cashmere number.
If you're looking for a stellar layering piece, this neutral knit offers you a sleeveless option to shake it up. Try it under a trench coat on a fall day, or paired with your favorite all black staples.
Get a knitwear confidence boost with this super sultry take on a white sweater. The rib knit makes it versatile for dressing up or down.
Made of a cozy cotton blend, this colorful sweater goes from reading on the sofa to meeting friends for drinks in no time.
Vintage-inspired, this cardigan from Lisa Says Gah is a dream for lovers of color and pattern. The pastel and neutral palette adds lots of fun without feeling overdone.
Nothing says Rich Mom quite like an open, shawlneck cardigan. Opting for chocolate brown instead of something light gives the look a sophisticated, timely vibe.
Cropped, half-zipped, and featuring a stunning cable knit, this cream sweater goes with just about anything. Wear it with black pants for a nice dinner and under white overalls for a country winter look.
Made of an alpaca blend, this drop shoulder crewneck sweater is a textural walk in the park. The subtle lime color matches almost anything, thanks to the marbled look.
This incredible knit is no "leave at your desk for when the AC kicks in" sweater. Paired with the matching pants, the look is unbelievable and a statement you'll want to rock all day long. But the sweater's equally as cool with a pair of jeans.
Feminine dressers, rejoice: This embroidered sweater is equal parts charming and coy, making it a great substitute for your favorite white blouse.
Color block is the name of the game when it comes to this statement sweater made to last. We love the half-sleeve and fresh take on neutrals.
Oversized and ultra-cozy, this sweater can be worn open or buttoned up to create a turtleneck style.
While this sweater's shape and gray tone make it easy to wear with anything, the raised popcorn dots add a fun detail to the lightweight yet cozy piece.
If you want to take trending olive shades from summer and fall statement pieces into chillier months, this half-zip sweater is a standout option.
This logo sweater will spice up the neutral collection in your closet.