Realistic School Drop-Off Outfits You Can Also Wear to the Office

There’s a whole category of outfits that need to do double duty: something you can throw on for school drop-off, but still feel confident wearing to the office right after. Whether your “office” is a Zoom screen, a coffee shop, or an actual corporate space, these are the outfits that make it easy.

They’re built around elevated basics and layers that look good, feel good, and don’t make you look like you rushed out the door (even if you did).

Shop products below:

OUTFIT 1: The “Leggings but Elevated” Look

• Brown oversized sweater

• White tee layered underneath

• Black stirrup leggings

• Classic black loafers

Why it works:
This is the easiest way to wear leggings without looking like you just left the gym. The oversized knit makes it intentional, the white tee softens it, and the loafers make it look like an outfit instead of loungewear. You could swap the loafers for sneakers and it still works, but the structure of the shoe is what keeps it office-ready.

Where it works:
Drop-off, WFH days with Zoom, coffee meetings, errands, casual office days.

Optional add-ons:
A trench, a crossbody bag, low bun or slick pony.

OUTFIT 2: The “I Didn’t Try, But It Looks Like I Did” Combo

• Navy knit sweater

• Chambray/denim button-down

• Mid-wash straight jeans

• Black riding boots

Why it works:
It’s a classic denim-on-denim moment without feeling too literal. The navy sweater adds structure, the button-down peeking out gives it layering without overthinking it, and the riding boots make it polished in seconds. It’s comfortable, it’s warm, and it looks like effort even if you got dressed in three minutes.

Where it works:
Drop-off, office days, lunch out, casual Fridays, travel days, weekend errands.

Optional add-ons:
A tote bag, black sunglasses, gold hoops.

If you want links, fit notes, or similar pieces, everything is saved on my LTK.
More school drop-off outfit posts coming — because this is daily life now.

— Lex