This Fall I Just Want to Dress Like Meg Ryan in ‘You’ve Got Mail’

Racked is no longer publishing. Thank you to everyone who read our work over the years. The archives will remain available here; for new stories, head over to Vox.com, where our staff is covering consumer culture for The Goods by Vox. You can also see what we’re up to by signing up here.

Whether a bouquet of freshly sharpened pencils sounds romantic to you or like a legit threat, no one can find You’ve Got Mail main character Kathleen Kelly’s impeccable style anything other than rousing. (Plus, that men’s pajamas game!) She’s smart but not especially pretentious; a Joni Mitchell fan descended from “enchanting.”

Legendary costume designer Albert Wolsky styled Meg Ryan for her 1998 role as the lovable independent children’s bookstore owner and daisy lover. Wolsky stuck to classic silhouettes in solid neutrals to balance out Kathleen’s earnest whimsy. This, too, coming from an age of handwringing over Borders wiping out mom-and-pop bookshops — long before “Prime” became shorthand for acquiring pantry staples, let alone the occasional subway read. (Were we ever so young?) The film’s independent, brick-and-mortar heart may occasionally ring dated or naive, but Kathleen’s wardrobe does not. There we have a series of layered masterpieces far more timeless than a tall skim caramel macchiato or, you know, dial-up.

Layering is crucial come fall, duh. The challenge may be daunting, but thanks to Kathleen’s shining light (or Wolsky’s wisdom, more likely), there’s a lot of inspo. Here’s how to shop like the girl around the corner.

Black mock turtlenecks are hard to coax outside of territories like “Judy Funnie entourage” and “high school theater tech hand,” but here is a good exception. Tucked neatly beneath a mossy green jumper with a chunky, oversized cardigan on top, the black mock turtleneck straddles the line of literary and posh.

Look as — sans sweater — it transitions into supportive-girlfriend-who-still-sticks-to-her-guns.

Less of a layering win, yet still notable: Kathleen’s party duds. It’s the black mock turtleneck again. (This one from Gap — on sale for $28 — is a dead ringer.) And with an important accessory! When navigating conversation with a dude explaining your own feelings back to you, this look truly resonates.

A camel cami and cardigan set make a chic, slightly melancholy blind first date get-up. It looks great, too, with the slate gray pencil skirt and Kathleen’s fav black tights/Oxford shoe comb — even if the fact she’s wearing her subway clothes in bed makes my skin crawl. (These Oxfords from Dansko look super similar — plus, Kathleen would surely appreciate the super comfy design, what with all that Upper West Side trotting.)

But the men’s-style pajamas!!

A tawny linen boatneck dress with full skirt and a cropped gray-blue button-down pair with this garden (and, spoiler alert, long-awaited smooch) like a goddamned dream. Please clap.