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Dressing Like a Bookstore Owner in the 90s (Meg Ryan Core).

By: Jen Shoop

I’ve been saying how I’ve been feeling very drawn to 90s-style pleated khakis as we head into fall (I ordered these and intend to wear belted), so I loved this Instagram post!

youve got mail fashion

Landon is heading out to a baseball game tomorrow night, and I will absolutely be watching “You’ve Got Mail” tomorrow night as a prelude to fall. Cannot wait. Need to dream up something cozy and fall-coded to enjoy alongside — maybe a batch of popcorn with some sort of fall seasoning (brown butter and paprika? or just my old faithful, this truffle popcorn?), a glass of red wine? Or maybe I’ll pick up a seasonal cupcake from Georgetown Cupcake. Maybe both! Going to put on a neutral knit set and chunky socks to channel Meg.

what to wear fall movies

NEGATIVE WAFFLE HENLEY, BRA, AND PANTS // WARBY PARKER GLASSES // EAST FORK POPCORN BOWL // TRUFFLE POPCORN // BOMBAS SOCKS

Now a visual homage to Meg in the 90s — loveeee the gamine silhouettes, neutrals, slouchy knits, loose hair!

Dressing like a bookstore owner in the 90s (Meg Ryan core) collage.

I’ve seen some really fab street style looks that echo Meg Ryan core recently — note the pleated khakis, the slim belts, cardigans and socks and a general slouchy vibe:

meg ryan inspired fashion
meg ryan inspired fashion

IMAGES VIA ONE // TWO // THREE // FOUR // FIVE

Some fun fashion finds to channel the look:

Dressing like a bookstore owner in the 90s collage.

BUTTON DOWN // TOTE // LOAFERS (USE CODE MAGPIE10) // JEANS // TRIANGLE SCARF // SHORT SLEEVE CARDIGAN // BELT

01. The pleated pants I ordered. Going to play around with styling. In my head, I’d wear with a cardigan, a cashmere triangle scarf, socks, and loafers (I own and adore these!!! use code MAGPIE10), but we will see how the proportions play out. Whatever I wear, the top has to be tucked in! Also, do I need red socks for my loafers a la the chic pea above?!

02. Adore the knot buttons on this cardigan — I own in gray. She’s a perfect Meg accessory. The slim cardigans from La Ligne (Ben style — super thin; use code MAGPIE10) and Ann Mashburn are also deeply on-theme.

03. Can’t get over this belt. Aureum makes THE chicest belts.

04. It doesn’t get more bookstore-owner core than this slim ladylike watch (use code MAGPIE20). Of course wouldn’t oppose a Cartier tank (suhwooon).

05. Love Warby glasses — thought this wire pair seemed especially Meg-coded.

05. Shop Around the Corner book tote! Perfect library book bag.

06. Per my note above: the ideal fall penny loafer. (Use code MAGPIE10.)

07. Denim pleated pants!

08. Pleated midi plaid skirt. Have actually been seeing skirts like this pop up all over the place — Me + Em, Wiggy Kit, Hunter Bell! This has major 90s Ralph Lauren energy. It also seems like something Meg would have worn with a black turtleneck and boots to Christmas dinner.

09. Suede dress to layer over a crisply starched white button down, a la Meg Ryan’s iconic look as owner of TSATC.

10. This cashmere argyle sweater and the matching triangle scarf. Obsessed. Gap released a similar triangle scarf last week!

11. Pleated chino skirt. Epic with the loafers and a slim fit cashmere sweater.

12. Meg owned the chunky turtleneck look — this sweater is a gorgeous homage to her.

13. These Banana Republic x La Ligne pants are a great fit for this motif. Would look phenomenal with the sweater above or a navy cashmere cardi.

14. Everyone needs a classic slim-fit turtleneck sweater.

15. Another great cashmere cardigan option — this one under $80.

16. A more contemporary twist: a short-sleeved cardi (unbuttoned just a tad) over a white baby tee with Agolde 90’s pinch waist denim. On the tee front: I just ordered two more of these (which just launched in new colors!) because I find I reach for them FIRST when looking for something to pair with athleisure. A little softer and more cropped than the SoldOut ones. I also ordered one of the long-sleeves to try!

17. Meg Ryan coded pajama set. Just add a box of kleenex and Tom Hanks buzzing up to your apartment.

18. Ultra-soft tipped robe to layer over top. My mom had one exactly like this growing up so it carries extra nostalgia for me!

Styling Meg Ryan Core.

Styling meg ryan core collage.

BARREL JEANS // LOAFERS // PLAID SWEATER // NECKLACE

Styling meg ryan core collage.

JEANS // SHORT SLEEVE SWEATER // LOAFER // PURSE

Styling meg ryan core collage.

PAJAMAS // ROBE // SLIPPERS

P.S. Movies that feel like a chocolate chip cookie.

P.P.S. The fall 2026 bag edit.

P.P.P.S. September tidings.

This post may contain affiliate links. If you make a purchase through the links above, I may receive compensation.

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