Go Big: How to Style Oversized Clothes

Two sizes too big? No problem. We’ll show you how to make that oversized shirt work for you (it’s easy!).

Last fall our Art Director, Catherine Maciunas, arrived at a photo shoot wearing the Cotton Nylon stand collar jacket—in a size three times larger than her usual fit. The jacket, a signature on our line, had so much added movement, drape and drama that it prompted many of us on set to ask, “oooh, which piece is THAT?”

At EILEEN FISHER, sizing has always been subject to interpretation. The simplicity of our designs means you can generally go up or down a size, depending on whether you’re looking for a more relaxed or body-skimming fit. But styling that supersized button-down shirt you found at the secondhand store? That may require a little more know-how to look intentional—and not like you’re playing dress-up in someone else’s clothes.

While we hope that our collection always inspires experimentation and play, it’s true that not every item lends itself to an oversized statement. The trick, explains Catherine, is to find the right pieces, ones with clean lines in fabrics that drape. If you’re new to the oversized look, she recommends going two sizes up (so if you’re usually a size M, try size XL). Or, if you live near an EILEEN FISHER store, you might consider spending some time trying on different shapes in a range of sizes to find the pieces that push your edge. But if there’s one takeaway it’s this: have fun with it. As Catherine says, “Attitude really is everything.”

The A-line jacket that started it all. To recreate this look with a jacket or coat from your own closet, look for a style with a straight or A-line silhouette in a fabric that has some movement and drape. Wear it open, or add a belt or cross-body bag, to create shape.

Nothing says cozy like an oversized sweater. You can't go wrong with tucking the hem into a pair of slouchy jeans or trousers. Another tried-and-true combo: the big sweater plus a cami dress. We recommend finding a sweater or cardigan that hits just below the hip.

An artful staple, the oversized shirt doubles as a lightweight jacket or beach cover-up. The trick is to roll up those billowing sleeves—showing off a narrower part of your body (like your wrist) helps balance boxy proportions. Another fool-proof tip: Pair it with high-waisted pants to create a leg-lengthening line. 

Tip from a stylist: The secret to keeping those rolled sleeves from slipping down your arms? “Hair ties,” explains Madison Daniels, EILEEN FISHER Brand Stylist. “On set, we use soft ribbon ties to keep sleeves in place. Just roll the cuff over the tie and push up.”  

Play with tucking or knotting an oversized tee to define your waist and control the volume. If laid-back and relaxed is more your mood, toss a T-shirt on with boyfriend jeans or slouchy ankle-length trousers—the tapered line is always flattering. 

When deciding whether to go oversized with a dress, look at the sleeves. A quick lesson in garment construction: Set-in sleeves are designed to hit at the top of the shoulder and can make an oversized piece look ill-fitting. Instead, look for a sleeveless dress or one with drop sleeves, identifiable by a seam that “drops” over the shoulder and hits at the upper arm. The lower the seam sits on your arm, the roomier (and more dramatic) the silhouette.


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