• March 14, 2026
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Photo-Illustration: The Strategist; Photo: Retailer

We are firmly in New York spring, a time of year when the temperature wildly oscillates between outdoor-dining weather and puffer-coat weather and then back again — sometimes within the span of a few days. The key to dressing effectively in this wonky weather is layers, and I’ll take that a step further and assert it’s the cotton sweater’s time to shine. In the depths of winter, I’m liable to toss on my cashmere sweater, but spring is perfect for a cotton one, which is less warm but still substantial enough to keep me comfortable. My personal favorite is the oversize Gap sweater, which I’ve raved about since purchasing a couple years ago. It’s so good that it’s made the rounds among Strategist staffers, who agree that it holds up over many washes and doesn’t lose its appeal. (So many of us own it that we’ve named it the Strategist’s Official “Boyfriend” Sweater.)

Photo: Tembe Denton-Hurst

The knit is the perfect weight for in-between weather—not so loose that wind and chill pass through easily and not so tight and chunky that I feel burdened about it. Its oversize fit also means I can layer a T-shirt underneath if need be, but it still fits nicely under my jackets. It’s 40 percent off at Gap right now as part of its sitewide Friends and Family sale, bringing it down to less than $50 — a deal so good I might just buy another.

Gap 100% Cotton Oversized Sweater




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Strategist writer Amelia Jerden just bought this super-discounted boatneck sweater …

… and this cable-crew sweater with an ultrachunky rib.

A close-fitting sweater that reminds me of a nice-looking long-sleeve.

This polo-style sweater is a little sheer, perfect for a nighttime event.

A mockneck sweater made of 100 percent cotton.

This sleek sweater is nicely constructed and the pink shade feels fitting for spring.


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The Strategist is designed to surface useful, expert recommendations for things to buy across the vast e-commerce landscape. Every product is independently selected by our team of editors, whom you can read about here. We update links when possible, but note that deals can expire and all prices are subject to change.



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