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. Tied around the neck, it feels preppy without feeling too stuffy.
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.
Oversized, neutral without being boring, and downright cheerful, this very Marimekko 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. Plus, stripes are always a good idea.
If polos have integrated their way into your wardrobe, why not embrace the trendy in sweater form? This darling look from Alex Mill 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 purple cardigan is surprisingly versatile. Pair with the matching bike shorts and tank tops for a luxe lounging look. Take it outside with a white shirt and vintage Levis.
This is the sweater for the sweater lover who's looking to invest in something special. "Hand vat-dyed in fermented persimmon fruit and cured in the sun for a orange-y beige color," the color is like nothing else, elevating all your other cold-weather basics.
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 Toast. Try it buttoned all the way up with your favorite jeans or leave it open over a jumpsuit for days 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 time neutral.
Feel good about this puff sleeved, cropped sweater for more reasons than one. Ten percent of the sale of this sweater goes to support the ACLU.
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.
While it's technically a poncho, this ingenious knit is just another argument against the idea that sweaters are boring. Try it over a trench coat, as pictured, or just on top of an all-black outfit.
Try out the trend of open, knitted tops with this super sultry take on a white sweater. The cropped hemline makes it versatile for tucking in and leaving out.
Made of 100% cotton, this cropped sweater goes from reading on the sofa to meeting friends for drinks in no time.
Vintage-inspired, this cardigan from YMC is a dream for minimalists and pattern lovers, alike. The greyscale coloring feels cool 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 little more relevance.
Wide, cropped, and slit in all the right places, 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 chenille and cotton, this drop shoulder crewneck sweater is a textural walk in the park. It matches almost anything, thanks to the marbled neutral look.
This incredible sweater is no "leave at your desk for when the AC kicks in" sweater. Paired with the matching pants, the look is unbelievable. But the sweater's equally as cool with a pair of jeans.
Feminine dressers, rejoice! This embroidered sweater is equal parts charming and coy, great for over your frilliest white blouse.
Texture is the name of the game when it comes to this ultra-special sweater made to last.
Oversized and ultra-cozy, this sweater can be worn open or buttoned up to create a turtleneck style.
While this sweater appears to be a simple, cropped crewneck from the front, the back reveals a lovely button detailing worthy of any holiday party or simply a Friday night.
If you don't want to pledge your allegiance to one school in particular, but still love the collegiate look, this striped quarter-zip offers the perfect compromise.
This fuzzy sweater will spice up the neutral collection in your closet.