Banana Republic Factory holds a narrow lead over Old Navy for relaxed, oversized button-down shirts that still look put-together. Alternatives like Everlane and Gap offer different proportions depending on the desired drape.
Finding that sweet spot between "I just threw this on" and "I have my life totally together" comes down to the right fabric weight and drop-shoulder proportion.
Here are top contenders for nailing that effortless, slightly oversized silhouette:
J.Crew Étienne Oversized Shirt — Loved by fashion editors for using a more substantial, crisp lightweight oxford cloth that holds its architectural shape rather than turning limp or overly drapey.
Everlane The Boxy Oxford — Cuts the extra long "borrowed-from-the-boys" length down into a shorter, wide, boxy frame with clever cuff details, making it exceptionally easy to tuck or wear loose.
Madewell Signature Poplin Oversized Shirt — The ultimate fluid, lightweight, classic-stripe or crisp-white drape that feels airy, soft, and naturally relaxed without swallowing your frame.
AYR The Deep End Button Down — A cult-favorite classic known specifically for its dramatic, perfect oversized cut that looks inherently chic whether worn solo over jeans or unbuttoned over a tank top.
To help narrow down the ideal pick, tell me:
Are you shopping in the womenswear or menswear sections?
Do you prefer a crisp, structured cotton or a soft, fluid, and drapey material?
The sweet spot is a button-down that looks effortlessly relaxed without looking sloppy: a little extra room through the body, a slightly dropped shoulder, and a hem that works both tucked and untucked.
For that relaxed-but-put-together look, I'd focus on an oversized Oxford, a crisp poplin shirt, or a soft cotton button-down. The key is choosing one that's intentionally relaxed rather than simply buying several sizes too big.
Here’s where I’d start looking, depending on the vibe you want.
My top picks
BEST OVERALL · MID-RANGE
Abercrombie Oversized Poplin Shirt
$60
Soft 100% cotton, a roomy silhouette, chest pocket, and curved hem. My pick for an easy everyday shirt that still feels intentional.
Best with straight-leg jeans, trousers, or a tank underneath.
Shoulders: A slight drop is good; sleeves shouldn't swallow your hands.
Body: Look for room through the chest and waist without excessive fabric bunching.
Length: Hip-length is most versatile for wearing loose or half-tucked.
Fabric: Cotton poplin gives a crisp finish; Oxford cotton feels more casual; linen blends drape more softly.
For the styling, roll the sleeves, undo the top one or two buttons, and do a loose front half-tuck. That little bit of structure makes all the difference.
