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There’s nothing better than a big, comfy sweater you can curl up in during winter, or a loose-fitting maxi skirt that blows around your ankles come spring. But as with everything, the too-big look didn’t come from nowhere. Through the decades the shapes and styles of oversized clothing changed as suited the times.

From head to toe, oversized clothing has had an impact on modern style. Whatever the reason, fashion always cycles back to the oversized look — be it with a bit of bling or a flowy maxi dress.

The 1920s: All that Glitters

Dresses like The New Woman’s Flapper Dress were designed to hang loose on a woman’s frame, but the layers and beads swung and shimmered with every movement so as to draw attention. Even jewelry burgeoned in size; pieces like Daisy’s Simple Chandelier Earrings would have stolen the show at any party. In fact, from rings to headwear, accessories were displayed as centerpieces of an outfit, not just accents.

But while flapper dresses have been relegated to the costume closet, large costume jewelry like the Anthro Knock Off Akela Necklace have made a serious comeback in current popular fashion. As new fabrics like jersey and new styles like the drop-waist dress became de rigueur in the 1920s, oversized garments and accessories quickly came into fashion. The overall style of the 1920s was a blend of relaxed, sporty daywear coupled with flashy eveningwear meant to catch—and hold—the eye.

 The 1930s: Fake It ‘Till You Make It

The 1930s were a rough time, economically—particularly for Americans, who were suffering through the Great Depression. Though movies featured ever more glamorous celebrities, the day-to-day reality of the average individual was far from the bright lights of Hollywood.

To combat the sharp fall in sales, designers began creating discounted products, relying more heavily on more economical fabrics like rayon and nylon. Even still, women were often forced to improvise. In order to achieve the puffy, oversized look of the film stars, women would sew fur to the hems of their garments, like this Fleece Scarf with a Fur Pocket or this Simple Faux Fur Infinity Scarf. Adding fur to a coat, scarf, or dress created a fabric contrast that both enlarged the garment and added a luxurious feel. A two-tone, flowy jacket like this Wrap Coat would have been a hit—both for the different fabrics and for the loose design.

The 1960s: Fun and Fancy Free

The 1960s were a time of radical change, particularly in women’s fashion.  This was the decade of  the miniskirt (and the midiskirt) and the A-line bodice. But it was also a decade that embraced the maxi dress. These flowing, fluid fabrics created the kind of easily elegant silhouettes that celebrities from Jackie-O to Joni Mitchell favored.

Dresses like this Chiffon Maxi Dress and the Effortless Caftan Dress wouldn’t have been out of place at a red carpet event. And of course no one can forget Jackie O’s notoriously overlarge sunglasses or the beehive hairstyle that was so radically popular. Loose, flowing, and big: the three keys to 1960s oversize fashion. Even the popular mod dresses of the time owed a debt to the oversized style of the 1920s flapper dress, as the cut was much the same, though mod dresses like this Cute Black and White Mini Dress emphasized a color block design, whereas flapper dresses keyed in to the movement of the dress on the body.

The 1990s and Beyond

The ’90s were a pretty hilarious time for fashion. Baggy, too-big, and grunge came with force to the forefront. From crop-tops to hammer pants, the ’90s were all about playing with perspective by emphasizing volume. These Zoot Alors pants, for example, might have walked off the stage of a concert or a red carpet at an awards show. This Easy Oversized Dress uses the same theory, gathering in and flaring out to emphasize contours and shape.

Current trends make a mix of history’s offerings. Enormous, comfy sweaters like the Asymmetrical Tunic Sweater, the Comfy Cardigan, and the Goncho Fleur de Lis Sweater all fit with that pattern. Looser-fitting t-shirts like the Draped Color Block Tee and the Shimmery Slouch Top also blend style with comfort.

What’s your favorite piece of oversized clothing?