The 5 Sweater Outfits I Keep on Constant Rotation in the Fall and Winter

Until I moved to New England, I didn’t realize how big of a commitment sweater season was. With no exaggeration, my sweater wardrobe is in strong rotation from about 9 out of the 12 months of the year. At peak winter, I reach cartoon character status, where I’m basically wearing the same sweater outfit almost every day in each episode of my life.

That said, I opened up my carefully stored sweater wardrobe earlier this fall with a pit in my stomach: I don’t actually want to wear ANY of these.

I like to think of myself as a responsible consumer, wearing pretty much everything I own into the ground. Not to say I’m exceptionally rough on things—I do try pretty hard to take great care of pieces that I think I’ll have forever—but heavy rotation due to lack of space can be tough on clothes. I frequently repair pieces, and generally like a mended aesthetic when I’m dressing pretty casually. Lucky for me, my sister is an expert-level knitter, and has darned many of my go-to’s out of the kindness of her heart. (My nagging also helped.) But sometimes, being the steward of threadbare pieces doesn’t do much for the creative soul.

I think I have reached my limit. I examined my sweater collection carefully, and there is no shortage of pattern, color, and texture. Basics are my Achilles heel, and, while patterned sweater doesn’t help much in repeat wear, it generally brings me joy. (Also, I find the latter to be way easier to wear than solid colors.)

After putting some of my old reliables back into the secondhand market and recycling those beyond further repair, it was time to consider some freshies. Following a formula of tried-and-true “patterns," I replenished the gaps, and am now encouraging readers to not shy away from busy sweaters—rather, embrace the fun and versatility these pieces bring in some of the most bleak days of the year. Here are five sweater outfits that I find hold up through repeat wear during the winter.

Striped Sweaters

A stripe acting as a neutral is a sartorial take I’ll take with me to the grave. For my sweater re-ups, I decided to shift away from my usual nautical and dabble in more collegiate stripes. I had to go straight to the source: Polo Ralph Lauren (via the Real Real).

Burgundy, navy, and gold were never the colors of any school I attended, but it seems like the School of Ralph owns this combo. I’ve seen styles in these colorways over the years (the brand has a few versions in its vintage capsule online), and, after I bought mine from the Real Real, I inception-ed myself into getting my kid an accidentally-matching one from Thredup.

I decided to “Ralph it up” even more when styling this sweater with a white linen maxi skirt, cowboy boots, a shearling trapper, a slick black leather belt and bag, and silver accessories. I know it will also look great with jeans or knit sweats on “throw-on-and-go” kind of days. This one may be my cartoon character choice of the season—watch this space.

Argyle Sweaters

A forever classic that has elbowed its way back into the fashion zeitgeist with appearances on the recent Miu Miu and Celine runways, argyle sweaters are feeling really right for right now. And I wanted in on it!

Damson Madder has been on my radar for its sustainability practices, and its take on the style in a punchy bright blue is a perfect marriage of my craving for something trendy that's also made with intention. (The 100% wool construction follows the responsible wool standard.) I paired it with my victorious Alaïa sample sale navy velour leggings, and played with some colorblocking by adding a Lindquist bag, olive socks, and a neutral sneaker. I also think this one will be fun to style over a slip dress with tall boots for a cozy winter date night or with shorts, socks, and loafers come spring.

Intarsia Sweaters

Intarsia (when a picture is woven into a knit) goes hand in hand with nostalgia, since these sweaters often feature childlike or scenic imagery that feels sweet and playful. My thoughtful friend Jenny tipped me off to this L.L. Bean style that has an intarsia dog nearly identical to my own sweet Peggy girl. I went oversized on this incredibly soft 100% cotton rollneck to give it a little more edge, and immediately added it to a classic “short skirt, long jacket” combo. I topped it off with some elf-like winter accessories, like a pompom hat and these chunky loafers from the recent Ugg x Sacai collaboration. The fact that it's made from a washable cotton makes it ideal to throw on with leggings on days I’m with my toddler, when a smudge of yogurt and/or playground dirt is inevitable.

Fair Isle Sweaters

While most of the iterations popping up everywhere are not knit on the Scottish island of which the style originated, it’s hard to resist that handmade-ish quality Fair Isle sweaters evoke. Sometimes this particular pattern can really scream “Christmas” to me, which gets a little awkward from January on, but it’s great to repeat all November and December long.

This shrunken one from Alex Mill is super intricate, crafted from a very soft merino wool. It reminds me of just a perfect vintage find. I tried to make it a little more kooky with a graphic pair of striped Junya Watanabe sweatshirt jeans, a flash of a red sock, suede boat shoes, and a vintage Chanel backpack to anchor the look. Popping it on over a turtleneck with jeans is a no-brainer, but I also could see myself wearing it with a pleated skirt and lace tights for a round on the holiday party circuit.

Cricket Sweater

A riff on the classic uniforms of the sport, a cricket sweater proves to be anything but boring. This graphic cable-knit is not exactly another stripe, but it’s not really a basic, either, which appeals to me greatly. I called upon Mr. Lauren once again for a fresh take, and love his version in cotton for easy maintenance, even if it’s white.

It’s hard not to feel kind of posh in one, but I also didn’t want to be super fussy. I grabbed a striped shirt and an old Saint Laurent denim skirt, and added a few prissy accessories, like a silk scarf and a pair of two-tone Chanel boots, which helped transition this otherwise preppy knit nicely into after work drinks with friends. Because of its weight and breathability, this one might actually be the winner for year-round wear! I can definitely see myself grabbing it for cool summer nights over a floral mini dress.