Cool Girls and Their Grandfathers Swear By These 9 Classic J.Crew Styles

models with trench coat and oxford shirt

(Image credit: J.Crew)

Whether you love or hate the fact that an "Eclectic Grandpa" aesthetic circling through the internet right now, you can't deny that the pieces that define the "grandpa" look are timeless pieces that'll kickstart any wardrobe. Cable-knit sweaters, classic loafers, and utility jackets were once associated with the older stylish set, but brands like J.Crew have added modern touches to bring the silhouettes into 2024. (Thank you, Olympia Gayot!) Think cashmere sweaters in cropped lengths, metallic loafers, and pastel-colored polo knits.

These items may be considered classic, but nothing about them is boring. Below, shop out the styles from J.Crew you'll catch both fashion folk and stylish grandpas sporting season after season. You'll be pleased with how many outfits you can create simply using the assortment below.


Whether you go for the cropped version or the vest silhouette, any of the three styles below will remain in your wardrobe for a long time.

Utility Jackets

Let utility jackets be the go-to outerwear piece in your wardrobe this spring.


Polos don't have to be stuffy, especially when they're crafted in cashmere and designed in pastel hues.

Classic Belts

Don't underestimate the power of a good ol' belt. J.Crew's options come at an affordable price point with quality comparable to higher-end brands.

Cashmere Sweaters

I have a trusty black cashmere sweater from J.Crew, and I'd be lying if I said I don't want to wear it everyday. Invest in the sweaters below and style them in a multitude of ways, whether you throw them over your shoulders or pair them with your favorite pair of jeans.

Oxford Shirts

Layer them under your knits or wear them as-is tucked into jeans, the options with an oxford shirt are endless. Instead of having to buy one from the men's department, I've noticed that J.Crew's options already have that slightly oversize and relaxed fit.


Don't let loafers only be worn with office or formal attire. Wear them with all your upcoming outfits, whether it be a T-shirt and jeans or a breezy dress.

Trench Coats

I don't like to call clothing items "needs," but I think a trench coat is just one of those pieces that deserves that title.

Retro Sneakers

No matter how polished the rest of your outfit is, a pair of retro sneakers will always add a relaxed touch to the outfit. Plus, they're extremely comfortable, so your feet will be thanking you. The green pair from New Balance below is sure to add a fun pop of color to your shoe collection.

Associate Fashion Editor
Yusra Siddiqui is an editor who resides in New Jersey but bounces between the suburbs and NYC. (She's a Jersey girl at heart.) After interning at Who What Wear in 2019, she found her way to the team after graduating from LIM College in 2022 with a fashion media degree. She's also spent time writing and working for publications such as Fashionista, Coveteur, and Nylon, but she always knew that Who What Wear was where she was meant to be. When she's on the job, she's perusing runway shows, analyzing the latest thing fellow Gen Zers are up to on the internet, and sharing what she can about the modest-fashion market. You can also catch her dabbling in entertainment, talking about the costume choices of the latest Netflix series or diving deeper into how the plotline affects the viewers in a myriad of ways. Lastly, she likes to create content for Who What Wear's TikTok. Her personal time is spent doing similar but also different things—deep diving into almost every new TV show (Bridgerton, Gilmore Girls, and Stranger Things are favorites), planning her next local getaway (whenever that may be), and reading the latest Emily Henry or Sally Rooney novel in one sitting.