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What to Wear Right Now: September / Back to School Edition.

By: Jen Shoop

Queue the “You’ve Got Mail” soundtrack…

What to Wear: Volunteering at School.

Or carpool, or errands, or ferrying the kids from activity to activity! What I love about this outfit is that the pants (use code EXTRACRISPY) are sweats/pajamas-level comfortable (pull-on, loose-fit) but you look so polished!

what to wear to volunteer at school

J. CREW BARN JACKET

CADETS PANTS

ALEX MILL CASHMERE BLEND ROLLNECK

FREDA SALVADOR CELESTE FLATS

GUCCI CROSSBODY

What to Wear: Shopping Downtown / Beergarden / Family Excursion.

A perfect formula for an outdoor excursion, featuring layers, loose-fit pants, and a crossbody that will keep you hands-free. Plus THE COOLEST JACKET. And I’m obsessed with this variegated striped cashmere sweater. I’ve been seeing stripes like this all over this season!

WHAT TO WEAR IN FALL

J. CREW CASHMERE SWEATER

LAYER OVER A THIN JERSEY BASE LAYER TEE — THIS ONE’S MY FAVORITE

ULLA J JACKET

LUNA PULL-ON CORDUROY PANTS

CUYANA CROSSBODY

MIU MIU RUBBER SOLE BOAT SHOES

What to Wear: Back to School Night.

A definitive cool mom look featuring of-the-moment bandana print pants, but with a blazer for a little polish — and this denim one is on ridiculous sale but low in stock. A classic navy would work just as well and may be more versatile as we head into true fall.

what to wear back to school night

VERONICA BEARD KIKI BLAZER (ON SALE)

TO DO LIST

BANDANA PRINTS

CHANEL BAG

MARGAUX FLATS

CARTIER BAGNOIRE WATCH (SWOOOOOON)

What to Wear: Book Talk.

For those of you coming to one of my book talks…hehe! (Please join me!!!). This look would also be great for a coffee date, a field trip chaperone moment, museum visit, etc. Note that this blazer is deeply, deeply discounted and delivers major Chanel vibes, and that the pleated pants are (at time of writing) on sale! I pre-ordered these a few weeks ago in a rush of envisioning myself as Meg Ryan in the 90s and can’t wait for them to arrive.

Last lil note: these A. Soliani denim Comos are probably one of my top two most-worn flats. They look so cool with EVERYTHING. A shirtdress, utility pants, jeans, cords! They just add that unexpected American irreverently casual vibe to anything. I love the toe box on these shoes.

what to wear this fall

VERONICA BEARD AINSLIE BLAZER (DEEPLY DISCOUNTED!)

EVERLANE PLEATED PANTS

LESET NANDO LONG SLEEVED TEE

CALL IT BY YOUR NAME BANDANA BAG

A. SOLIANI DENIM FLATS

What to Wear: Convocation, Teacher Meeting, Board Meeting.

The contrast trim on this tweedy dress is SO GOOD. Polished but not too up-tight. Layer beneath a cardigan with a little pattern for contrast. Doen’s knitwear is insanely good! I wore my fair isle cardigan from them ALL SEASON LONG. And the watch just looks like an heirloom!

what to wear this fall

ME + EM DRESS

DOEN SWEATER

VERONICA BEARD BOOTS

JANE WIN PENDANT

CENDRE WATCH

LORO PIANA CALF-HAIR BAG (OMG)

What to Wear: Fall Garden Goddess.

In another life, I live in a small English cottage and putter about in a garden while the tea kettle is whistling. As I write that, I am remembering when I texted my sister, earlier this week, “in another life, we own a romance bookstore in the Cotswolds,” and she replied: “Why not this life?” Lol! Love that energy. Anyway, this is what my quaint English doppelganger would wear:

fall gardening

IF ONLY IF NIGHTGOWN

CLOTHBOUND SENSE AND SENSIBILITY BOOK

DOEN CARDIGAN

CROCS BOAT SHOE

HAWS WATERING CAN

What to Wear: Football Viewing.

Fantasy football season is closing in on us. Sigh. Lol. This is what I’d wear to a Sunday afternoon hang out — easy sweatshirt and jeans but with a little interest. These jeans have been a top Magpie seller. The dark rinse denim makes them ultra-relevant.

what to wear this fall

DONNI SWEATSHIRT

HILL HOUSE JACKET

SAVETTE BAG

LUG SOLE SPERRY

DARK RINSE DENIM

P.S. What I’d tell my 20-year-old self.

P.P.S. Thoughts on becoming an expert in yourself.

P.P.P.S. One of my favorite books this summer.

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