How I’m Updating My Fall Wardrobe Before School Drop-Off Season Hits

Photo Credit:@emanosmann

Somewhere between buying 24 glue sticks for the school supply list and scheduling dentist appointments before the end of summer, I realized something: my fall wardrobe was basically on the back burner.

And listen — when you’re juggling drop-offs, work calls, and the occasional coffee with friends, you don’t just need outfits, you need outfits that work hard without looking like they work hard.

This year, instead of panic-buying whatever I could grab between errands, I made a plan. I wanted pieces I could wear on the playground, in the office, and even out to dinner without feeling like I was wearing “mom clothes” in the traditional sense.

Here’s my back-to-school shopping list — curated with style, comfort, and real-life chaos in mind.

The School Drop-Off Layer

For those chilly September mornings where you need something you can throw on over pajamas but still wave at other parents without shame.

Old Navy

Fit & Flare Sleeveless Denim Midi Dress

$49.99

The Work-to-PTA Meeting Dress

One that looks polished enough for client Zoom calls but isn’t so precious you can’t sit on bleachers at the fall pep rally.

Old Navy

Smocked Midi Skirt

$39.99

The Coffee Run Sweater

Because even when you’re just running for caffeine, a good knit can make you feel like you have it together.

Old Navy

SoComfy Oversized Graphic Raglan Sweatshirt

$39.99

The Multipurpose Denim

The pair you can wear for errands, Friday night football games, and date night if you swap sneakers for boots.

Old Navy

Extra High-Waisted Wide-Leg Jeans

$49.99

The “Surprise Meeting” Blazer

Keeps you looking sharp for that last-minute parent-teacher conference or when you run into your boss at Target.

Quince

100% Leather Blazer

$250.00

The After-School Sneakers

Comfortable enough to chase kids, chic enough that they work with a midi skirt.

Adidas

Cloudfoam Pure Shoes

$75

The Saturday Soccer Sideline Coat

Warm, weatherproof, and cute enough for brunch after the game.

Old Navy

Oversized Jean Trucker Jacket

$54.99

The Playdate-Approved Tote

Big enough for snacks, coloring books, and the inevitable “Can you hold this?”

L.L Bean

Boat and Tote®, Zip-Top

$49.95

The Layer-Under-Everything Turtleneck

The quiet MVP of transitional dressing — perfect for under cardigans, jackets, or jumpers.

Quince

Cotton Cashmere Ribbed Turtleneck Bodysuit

$39.90

The Easy-Upgrade Accessories

A good pair of hoops, a structured bag, and a scarf that makes you look instantly put together.

14K Gold Interlocking Stackable Rings

$15.99

Planning your fall wardrobe? Don’t miss the Fall Wardrobe Checklist — it’s the go-to list for layering like a pro without overthinking your outfits.