From unique bags to fun socks, here are 7 ways to add whimsy to your wardrobe

I’ve always liked colour, but if you looked at my closet mere months ago, there would be no indication of it. I’d collected earth tones and shades of grey in the hope that if everything matched, it would be easier to put together an outfit. I dressed with seriousness and followed formulaic fashion rules (no, actually, your belt does not have to match your shoes). My search for efficient dressing made me boring. It took the fun out of fashion. And I wanted it back. I wanted to wear clothes that made me feel happy, no matter how ridiculous they were. I wanted to be whimsical.

In Donald Miller’s A Million Miles in a Thousand Years: What I Learned While Editing My Life, Miller recalls asking someone to define whimsy. He struggled to put it into words, eventually describing it as “that nagging idea that life could be magical; it could be special if we were only willing to take a few risks.” I had been risk-averse, and as a result my style was devoid of magic. That feels like a pretty good reason to chase whimsy—not in way where you look as though a six-year-old has styled you, are covered in bows or look like a fairy (unless you want to)—but about play, and letting yourself be silly.

Artist and content creator Emma Foss, who runs Y Street Studio, where she sells nature-inspired art, has been on a jouney to whimsify her wardrobe, exploring this territory largely with upcycling, DIY hacks and looking at ordinary things with a slightly more curious eye. Her inspiration comes from Pinterest, other artists or an occasional walk outside. “There are times when I’ll see some leaves, and it’ll remind me of a sequin and I’ll wonder if I could make similiar-looking sequins out of upcycled acetate,” she says.

Foss’s approach to upcycling is a good example of where to start. Her old jacket upcycled with rows of buttons arranged in geometric lines shows “how you can be whimsical and elevated at the same time”. After taking some cues from Foss—and experimenting with a few of my own—I’ve put together a guide to making clothes a little more fun.

1. Bags do not have to be bag-shaped

“If you’re nervous to dress more crazy, a fun purse feels a lot less intimidating than wearing a giant balloon dress,” says Foss. Wonderfully unique bags can do a lot of heavy lifting without requiring you to rethink your entire outfit. Accessories can be a gateway into larger fashion experiments.