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What I’d Wear, Vol. III.

By: Jen Shoop

Seen above: Maison Le Comte wool-silk shawl scarf; Soeur sherpa bag; Guest in Residence fringed cashmere jacket.

I’m back with another installment of outfit formulas for various seasonal events we may be attending in the coming week or two. Below is what I’d want to wear for the events that are specifically on my calendar —

What to Wear: Back to School Event.

We have another back to school event (we get to audit my daughter’s morning, walking around with her from class to class!) coming up. Below is what I’d wear in an ideal world…very “grown up back to school.”

back to school parents outfit

VERONICA BEARD BLAZER (LOOK FOR LESS HERE, HERE, HERE) // ALEX MILL CASHMERE POLO SWEATER (LOOK FOR LESS HERE, HERE) // AGOLDE REN JEANS // A SOLIANI COMO FLATS* // TOTEME BAG // ELECTRIC PICKS CHUNKY GOLD HOOPS**

*I’ve admired this brand from afar since I first spotted Julia Amory wearing a few pairs of this brand last fall. I finally ordered a pair and they are absolutely fantastic. They are similar in quality and finish to the Margaux ones we all know and love, but have a slightly longer toe box which I think makes them a tad more comfortable. I wore them three days straight (with lots of walking!) and can’t rec more. Run TTS. These flats look like they cost multiples of their price tag — quiet luxury for sure. They could pass for Khaite or Manolo or something.

**These are the exact kinds of earrings I’m reaching for at the moment to finish every fall look. Use code SHOOP20 for 20% off — well under $100! I have a pair from Mega that are similarly chunky and gold that I adore.

What to Wear: Dinner with Parents.

I’m just back from a lovely two night stay in rural PA with my parents, and this is exactly what I wore to dinner — the only swap is that my suede cropped jacket is past season Talbots (!!! — such a good score, I still can’t believe it), and the one below is lust-worthy Nili Lotan. I’ve linked a few other similar suede cropped jackets at different price points if you’re in the market: Madewell, Anthro, and Brooks Brothers.

what to wear to dinner with in-laws

SUEDE CROPPED JACKET (LOOK FOR LESS HERE) // THE GREAT TULSA DRESS (SIMILAR VIBE FOR LESS HERE) // SCAROSSO LOHAN SUEDE MULES // LIZZIE FORTUNATO EARRINGS // SOEUR SHERPA BAG // THE OUTSET LIP OASIS IN NUDE

What to Wear: Fall Outing.

I wore a version of this outfit while traveling with my parents, enjoying lunch with them, etc. All the fall textures and colors.

what to wear on a fall outing

SANDRO JACKET (LOOK FOR LESS HERE, HERE, HERE) // ALIGNE DION SWEATER (LOOK FOR LESS HERE) // PISTOLA WIDE LEG CROP CORDUROYS (LOOK FOR LESS HERE AND HERE) // BOAT SHOES (UNDER $100!) // TUCKERNUCK WOOL BLEND SCARF

What to Wear: Wine with Mom Friends.

I am looking forward to a couple of dates with mom friends after the rush of September has settled down a bit —

what to wear wine night with friends

HILL HOUSE SCARLETT DRESS // GUEST IN RESIDENCE SCULPTED SWEATER (VIBE FOR LESS HERE, HERE) // JENNIFER BEHR EARRINGS // HUNTING SEASON CLUTCH // TECOVAS BOOTS

What to Wear: Carpool / Play Date.

This weekend, I’m taking two of my daughter’s new friends from her new school (and my daughter) to get boba teas! A cute little weekend date to help them cultivate those new relationships. I’ll be wearing something similar to this — note that these overalls are CORDUROY (!!!) and $108!

what to wear carpool outfit

GAP CORDUROY OVERALLS // RIBBED BUTTON-DOWN (50% OFF!) // UNDO MINI HAIR CLIP // CALL IT BY YOUR NAME BANDANA TOTE (LOOK FOR LESS HERE) // BIRKS // GLASS TO-GO CUP

What to Wear: Dinner Date with Landon.

I snagged reservations at newly-opened Maison DC, a wine bar and sister restaurant to Lutece and Pascual (both of which Landon and I loved!), and I can’t wait to dress up for a night out with him. We’ve had such a fun and busy social calendar the past few weeks, but it feels like we’ve not spent a ton of time just the two of us. Looking forward to this date night, and my dream outfit for it below —

what to wear dinner date

LA DOUBLE J BLOUSE (SIMILAR VIBE FOR LESS HERE) // SHASHI EARRINGS (UNDER $100!) // LA LIGNE COLBY PANTS (LOOK FOR LESS HERE) // MULES (UNDER $60!) // BOTTEGA BAG

What to Wear: Country Concert.

I’m going to a country concert with friends this weekend! The weather is looking warm so I’ll probably wear this denim dress with “Western” accessories (belt, boots?) but this is the vibe I initially dreamt up. (More concert outfit ideas here!)

what to wear country concert

SEA DENIM JACKET (THE LACE CAPE, OMG!) // THE GREAT HENLEY TANK // VERONICA BEARD TAYLOR JEANS (LOOK FOR LESS HERE, HERE) // MARC FISHER BOOTS // CLEAR CONCERT BAG ($26!) — I’D WRAP THIS BANDANA — LOOK FOR LESS HERE — AROUND THE HANDLE

What to Wear: Cozy Night In.

I have been reading this cozy small town romance before bed this week. It’s set in the 90s and has a super nostalgic, almost sit-com-like feel to it and a very slow-burn neighbors-to-lovers story. (All my top fall reading recs here.)

cozy reading night in

LAKE PAJAMAS KNIT SET (GO DOWN A SIZE – THE PANTS RUN REALLY BIG) // CHAPPYWRAP BLANKET (15% OFF THIS MONTH WITH CODE JEN15) // HYDRATING MASK // PRADA SLIP-ONS // FAVORITE FALL CANDLE (USE CODE MAGPIE10) // IF IT MAKES YOU HAPPY BOOK // MICROCHIP COOKIES

P.S. What does happiness look like?

P.P.S. Benedictions.

P.P.P.S. Praise song for the people who keep the lamps lit.

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

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