9 Rollneck Sweater Picks for Winter Travel

I’ll be the first to admit that the piles of sweaters practically spilling from my closet should be the first indicator that I’m not exactly in the market for another new knit in my collection. But after years of trial and error, I had still yet to find a pullover that exuded the carefree nature and vintage charm of the sweaters I’d spotted in my mom’s closet growing up. That is, until my attention was directed to J.Crew’s selection of rollneck sweaters.

I hemmed and hawed for months, surveying the selection of men’s and women’s offerings. After careful consideration, it was the men’s 1988 Rollneck Sweater in a heavyweight cotton that I opted for, with a loose, drapey fit sans the ribbing of the best-selling women’s 2025 Rollneck Sweater. Since I unwrapped the sweater for my birthday in August, it’s been the first thing I pack in my suitcase regardless of the climate of my destination—and now that the style has gone viral, I feel vindicated in my choice. 

J.Crew 1988 Rollneck Sweater

With its raw hem, drop shoulders, and perfectly boxy fit, this impeccably made sweater swiftly became a favorite in my wardrobe. Its quality is evident in the weight and feel of the knit. It pairs just as well with my favorite pair of jeans as the flowy maxi skirt that’s another packing list staple, and it’s so soft that I don’t have to layer a top beneath it to wear it comfortably. Since I have wider hips, I generally struggle to find an oversized sweater that actually skims my body without clinging to it, and the relaxed weft of this knit finally fulfilled my dreams of a throw-on-and-go sweater that doesn’t warp my body or drown my frame. 

It’s made from 100 percent cotton, so it’s machine washable, which is essential since I’m never in the mood to hand wash or dry clean my favorite pieces—and in the four months I’ve owned this sweater it’s already gotten enough wear that it’s required frequent washing. And since we’re in the heart of winter, I especially appreciate its heavyweight design that will actually keep me warm (and can be easily layered under my favorite jackets).

J.Crew 1988 Rollneck Sweater

While selecting my colorway last summer, the iconic rollneck sweater was available in a far more limited shade range. Now it comes in six beautiful hues, including navy, heather sky, and red ochre—the most delicious tomato red I’m eyeing as a gift to myself. Since I was looking for a baggier fit, I found the medium to be perfect (even in men’s sizes), although it’s also available from 2XS to 2XL. 

Being that it’s a garment I’ll likely have at the forefront of my closet for the rest of my life, the J.Crew 1988 Rollneck Sweater was an entirely worthwhile investment into my wardrobe at $98. But, if you’re still looking for the perfect knit for your packing list, keep reading to find more rollneck sweaters that’ll make you the best-dressed traveler at any destination, starting at just $30.

More Rollneck Sweaters to Shop for Winter

Banana Republic Cable Rollneck Sweater, $43 at Checkout

Currently double-discounted to $43, this beautiful cable-knit sweater is the perfect oversized pick for your winter travel plans, and it’s especially flattering with split hems and a slight rollneck design. Made from a soft, stretchy cotton blend, the slouchy sweater exudes style and can be worn loose or tucked in depending on the bottoms you’ve opted for that day. It comes in sizes 2XS to 2XL so you can choose a breezy or snug fit, and it’s available in three timeless shades.

L.L.Bean Men’s Organic Cotton Rollneck Waffle Sweater

Experimenting with texture is a great way to set new pieces apart from your existing sweater collection. This 100 percent cotton waffle-knit pullover from L.L.Bean is an excellent pick that comes in an impressive size range with regular and tall lengths available to accommodate a larger swath of shoppers. The heavier weight will make it the first sweater you slip on for chilly sightseeing days throughout the winter months, and it’s machine washable for convenient care. While it is a men’s sweater, it’s a great choice for anyone looking for a snuggly, oversized fit. 

Free People Opal Rollneck Knit Sweater

For a more feminine take on the rollneck trend, the Free People Opal Rollneck Knit Sweater will fit wonderfully into your wardrobe, providing warmth and style all in one. The cropped, raw hem is both trendy and effortlessly cool, while drop shoulders create a casual finish that’s easy to throw on in-flight or on the go. It’s constructed from a lightweight cotton knit that’ll transition easily from winter to spring, but the biggest selling point is the eye-catching 13 color range. 

Saodimallsu Oversized Pullover

Similar in appearance to the women’s version of the J.Crew Rollneck Sweater, this oversized pullover from Amazon is a far more affordable pick at $30. It features ribbing at the hem, neckline, and sleeves that adds thoughtful detail to the simple sweater. The sleeves boast a wide, batwing style that’s super casual and comfy without restricting your movement. It’s even earned thousands of five-star ratings from happy shoppers, with one customer noting that not only was it “very comfortable and warm,” but it also “held up on vacation.”

Greaidea Pullover Sweater

Another wallet-friendly Amazon pick, this simple, baggy pullover is a dreamy knit that’ll be a breeze to style countless different ways throughout any vacation—and its slightly rolled neckline is perfectly on trend for the season. The sweater is oversized, falling well past the hips, but slits at either side of the hem ensure it’s still flattering and allow for movement without feeling too rigid. It comes in five neutral colors (all of which are on sale for just $30), and the boxy cut looks best worn loose with anything from jeans to sweatpants. 

Free People Torres Turtleneck Sweater

Made from a 100 percent cotton knit, the Free People Torres Turtleneck Sweater should remain at the top of your packing list no matter your destination this winter—and you can’t go wrong with any of its four pretty shades. Unlike other rollneck styles, this sweater has a higher, slouchier neckline and batwing sleeves that create a loose, casual finish that can be dressed up with a skirt or down with a pair of worn-in jeans. It’s incredibly soft and machine washable, so you don’t have to worry about maintenance being a hassle, and it’s thick enough to actually keep you warm as the temperatures drop. 

Lands’ End Men’s Long Sleeve Rollneck Sweater, $36 with Coupon

If you prefer your sweaters to have a more structured fit, the Lands’ End Men’s Long Sleeve Rollneck Sweater will be your best bet—and right now it’s 64 percent off. Both the sleeves and hem of the pullover are decorated with ribbing, which contrasts with the plain knit of the body. The yarn is flecked to add vintage charm to this high-quality sweater. Its cotton blend is mixed with wool for additional warmth and insulation against the elements. It can be worn on its own or layered beneath a lightweight trench, depending on the weather. 

Aran Crafts Plain Knit Curl Neck Sweater

Simple in design yet incredibly cozy and well-structured, this 100 percent wool Irish sweater will be the MVP for keeping you warm this season. The timeless knit has a rolled neckline and sleeves, and the body of the sweater is slightly boxy and relaxed but will still layer well under a coat as needed. Even if you can’t make it over to Ireland anytime soon, you’ll be transported by the classic weave that’ll keep you well dressed from Dublin to the Cliffs of Moher. comes in three beautiful shades that’ll match every pair of pants in your suitcase. 

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