9 Rollneck Sweater Picks for Winter Travel

I’ll be the first to admit that the piles of sweaters practically spilling out of my closet should be the first clue that I’m not exactly in the market for another new knit in my collection. But after years of trial and error, I had yet to find a pullover that pulled off the carefree nature and vintage charm of the sweaters I grew up in my mom’s closet with. That is, until my attention was drawn to JCrew’s selection of rollneck sweaters.

I reviewed a selection of men’s and women’s offerings for several months. After careful consideration, it was the men’s 1988 roll-neck sweater in a heavyweight cotton that I chose, with a loose, drapey fit that bucks the ribbing of the best-selling women’s 2025 roll-neck sweater. Since I wrapped up the sweater for my birthday in August, it’s been the first thing 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 Roll Neck Sweater

With its raw hem, drop shoulders, and perfectly boxy fit, this impeccably tailored sweater quickly became a favorite in my closet. Its quality is evident in the weight and feel of the fabric. As well as my favorite pair of jeans, the maxi skirt is another packing list staple, and it’s so soft that it doesn’t need to be layered with a top to wear it comfortably. Because I have wide hips, I usually struggle to find an oversized sweater that actually flatters my body without clinging to it, and this cozy knit weft finally made my dreams come true. does not Dodge my body or sink my frame.

It’s made from 100 percent cotton, so it’s machine washable, which is important because I’m not in the mood to hand wash or dry my favorite pieces — and in the four months I’ve owned this sweater it’s already seen enough wear that it needs 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 easily be layered under my favorite jackets).

J Crew 1988 Roll Neck Sweater

When choosing my colorway last summer, the iconic rollneck sweater was available in a much more limited shade range. It now comes in six gorgeous colors, including navy, heather sky, and red ocher—the most delicious tomato red I’ve ever seen myself gifting myself. Since I was looking for a baggy fit, I found the medium to be perfect (even in men’s sizes), although it’s also available from 2x to 2xl.

It’s a dress that will be at the forefront of my wardrobe for the rest of my life, the JCrew 1988 Rollneck Sweater was a totally worthwhile investment in 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 will make you the best-dressed traveler on any destination, starting at just $30.

More Roll Neck Sweaters to Shop for Winter

Banana Republic Cable Rollneck Sweater, $43 at checkout

Currently on sale for $43, this gorgeous cable knit sweater is the perfect oversize pick for your winter travel plans, and it’s especially flattering with the split hems and modest roll neck design. Made from a soft, stretchy cotton blend, the raw sweater can be worn loose or tucked in depending on the style and bottoms chosen for the day. It comes in sizes 2xs to 2xl so you can choose an airy or snug fit, and it’s available in three timeless colors.

LLBEAN Men’s Organic Cotton Rollneck Waffle Sweater

Experimenting with texture is a great way to define new pieces in addition to your existing sweater collection. This 100 percent cotton waffle-knit pullover from LLBean 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 heavy weight will make this your go-to sweater for chilly days in the winter months, and it’s machine washable for easy care. Although it’s a men’s sweater, it’s a great choice for anyone with any type of, oversized fit.

Free People Opal Rollneck Knit Sweater

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

Sodomalso large pullover

Like the women’s version of the JCrew rollneck sweater, this oversized pullover from Amazon is a much more affordable choice at $30. It features ribbing on the hem, neck and sleeves that add thoughtful detail to a simple sweater. The sleeves boast a wide, batting style that’s super comfortable without restricting your movement. It’s even earned thousands of five-star ratings from HappyShoppers, with one customer noting that not only is it “very comfortable and warm,” it also “held up on vacation.”

Gradia pullover sweater

Another wallet-friendly Amazon pick, this simple, baggy pullover is a whimsical knit that will be a breeze to style in countless different ways on any holiday. The sweater is voluminous, falls well from the hips, but slips on either side of the hem ensuring it’s still flattering and allows for movement without feeling too tight. It comes in five neutral colors (all of which are on sale for just $30), and the boxy cut looks great worn loose with anything from jeans to sweats.

Free People Torres Turtleneck Sweater

Made from 100 percent cotton, the Free People Taurus Turtleneck Sweater should be at the top of your packing list no matter where you’re heading this winter—and you can’t go wrong with any of its four gorgeous colors. Unlike other roll neck styles, this sweater has a high, sloucher neckline and batting sleeves for a loose, relaxed finish that can be dressed up with a skirt or dressed down with a pair of jeans. It’s incredibly soft and machine washable, so you don’t have to worry about maintenance hassles, and it’s thick enough to keep you warm as the temperature drops. Actually keep you warm.

Land’s 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 Roll Neck Sweater would be your best bet. Both the sleeves and the hem of the pullover are decorated with ribbing, which contrasts with the plain knit of the body. The yarn is flocked to add vintage charm to this high-quality sweater. Its cotton blend is blended with wool for extra warmth and insulation against the elements. It can be worn on its own depending on the weather or layered under a lightweight trench.

Aran Handicraft Plain Knit Curl Neck Sweater

Simple in design yet incredibly comfortable and well-constructed, this 100 percent wool Irish sweater will be the MVP for keeping you warm this season. The timeless knit features a rolled neck 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 to Ireland anytime soon, you’ll be transported by the classic weave that will keep you well-dressed from Dublin to the Mountains of Moher. Comes in three gorgeous colors to match every pair of pants in your suitcase.

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