We’re back for Fashion You’ll Actually Wear Week with indisputably the most fun category. Staying in or going out (even just to run errands), these outfits are ready for anything.
theSkimm

September 10, 2025

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Fashion You'll Actually Wear Week: The Play Edit

We’re back for Fashion You’ll Actually Wear Week with indisputably the most fun category. Staying in or going out (even just to run errands), these outfits are ready for anything.

 

CHECK OUT OUR OFF-DUTY PICKS

 
Baggy Dad Barrel Jeans

LEVI’S

Baggy Dad Barrel Jeans

$108 AT LEVI’S

The baggy dad jeans you love, but with a chic barrel-leg silhouette.

The baggy dad jeans you love, but with a chic barrel-leg silhouette.

2025 Rollneck™ Sweater

J.CREW

2025 Rollneck™ Sweater

$98 AT J.CREW

Maturing is realizing how versatile a good cotton sweater is.

Maturing is realizing how versatile a good cotton sweater is.

We The Free Baby Emerson Tote Bag

FREE PEOPLE

We The Free Baby Emerson Tote Bag

$178 AT FREE PEOPLE

The perfect mix between a tote and a bowler bag.

The perfect mix between a tote and a bowler bag.

Bra-Free 90s Cami

ABERCROMBIE & FITCH

Bra-Free 90s Cami

$29 AT ABERCROMBIE & FITCH

We’ve been wearing this nonstop and can confirm: no bra is required.

We’ve been wearing this nonstop and can confirm: no bra is required.

What to Wear on the Weekends When You’re Running Errands

What to Wear on the Weekends When You’re Running Errands

GETTING COFFEE COUNTS
High-Waisted PowerSoft Rib Leggings

OLD NAVY

High-Waisted PowerSoft Rib Leggings

$9.99+ AT OLD NAVY

Old Navy activewear is elite. These are no exception.

Old Navy activewear is elite. These are no exception.

Organic Cotton Poplin Big Shirt

GAP

Organic Cotton Poplin Big Shirt

$69.95 AT GAP

A nice button-up will never fail to make you feel put-together.

A nice button-up will never fail to make you feel put-together.

Classic Jean Jacket

OLD NAVY

Classic Jean Jacket

$27.99+ AT OLD NAVY

A classic denim jacket never goes out of style.

A classic denim jacket never goes out of style.

Italian Leather Pointed Bow Flat

QUINCE

Italian Leather Pointed Bow Flat