I love to dress up. And I’m not just talking about putting on a dress, high heels, and some makeup. When I dress up, it is full-blown, exhaustive, with all stops pulled out. There are hats, gloves, sequins, metallics, glitter, bloomers, petticoats, and gobs and gobs of blush. Call it theatrical dressing, everyday costuming, Xtreme style for Xtreme times. All you need to pull it off is some imagination and a big dose of confidence. Because when you are wearing a see-through tutu, sequined knickers, Victorian granny boots, a corset, and a rakish bowler—an outfit I once dreamed up but never executed because of a lack of some of the key pieces—people will stare. And you have to learn to enjoy it, or at least not mind.

I was never a particularly bold sort of person. My first instinct in any social situation was (and still is) to blend into a corner, pretending to be invisible. “Oh no, it’s just little old me! Please don’t pay me any attention!” But deep down inside there has always lurked a secret desire to be in the spotlight, to be different, to boldly go where women are actively discouraged to go. Even while I hid in baggy, shapeless blacks, I was constantly flipping through fashion magazines at the store (I was too embarrassed to buy them) to admire the editorials—all those weird, outrageous, amazing clothes that no self-respecting person would dare to wear (they wouldn’t, right?). Now I wear weird, outrageous (and hopefully amazing) clothes all the time. So what changed? Well, confidence.

In 2011 the fashion photographer Velvet D’Amour asked me to pose for some photos. I was unbelievably flattered; modeling for a fashion magazine was something I had previously only dreamed of. Velvet dressed me in tutus, corsets, a harness, and six-inch heels, topped by a pile of fake hair and an assortment of extravagant lace headpieces and had me bouncing around on a gigantic fluorescent exercise ball. As you might imagine, people stared. Some commented. It was unnerving at first. But here I was doing something I had always secretly wanted to do, and after about 10 minutes the thrill of that started to outweigh my discomfort, and soon I found I just DID NOT CARE what anyone else thought. I stood in the middle of the market in my (frankly painful) heels, twirling a cane and posing my heart out. It was scary, but it was also really exhilarating and liberating and empowering. Never again was I scared to go out in public in whatever the hell I wanted. All the world was my stage, and my clothes were my costume.

That shoot wasn’t a magic bullet—I didn’t go from wallflower to butterfly in one afternoon. It was the final push I needed after a long process of experimenting with my personal style. Confidence takes time and serious effort to develop. It takes lots of experimentation and rejection and stumbling and getting back up again. I think you have to be derided/mocked/insulted over and over and over before you get sick of paying attention to what other people think of you. If you’re scared of dressing the way you want to because of other people’s reactions, start collecting their shitty comments like badges of honor. Keep score. For every 10 insults, give yourself a reward: some bananas article of clothing you’ve been eyeing, or a fashion magazine, or a trip to the craft store for DIY supplies. Pretty soon other people’s negativity will start to sting less, and you might start to feel a little ego/happiness boost every time someone tries to put you down because of your outfit. You may even begin to feel sorry for them. Eventually you will stop even thinking about them. Voilà: confidence.

That’s the first thing you’ll need to dress like you’re onstage, in a silent movie, on the vaudeville circuit, or in the circus. Here’s the rest:

(Wait, a quick caveat: I don’t believe in “fast fashion”—stuff that’s cheaply made and cheaply sold—because I’m concerned with the human-rights and environmental abuses practiced by most of the big chains that sell trendy clothes at super-low prices, and because I buy clothes with the intention of wearing them for the rest of my life, so they have to be made to last. So some of the stuff I’m gonna suggest here might be a bit of an investment—but I think you get what you pay for!)


Top left: Knee-length Sisters of the Moon tutu, $45, Etsy. Bottom left: American Blossoms tutu, $60, Etsy. Right, Georgina of Cupcake’s Clothes.

I consider a tutu or a tulle skirt a wardrobe essential for every girl or boy. Get a ready-made one like the styles above, or make your own!


Left to right: Phone Booth Belle Dress, $125, ModCloth; Sea Shanty Singing Dress, $130, ModCloth; Elin on Lookbook.nu.

Sailor style is always great for theatricality, especially when you add a hat! I absolutely adore these two dresses.


L–R: Top of the Byline Dress, $80, ModCloth; Star Carousel dress, $165, Gloomth’s Haunted Circus; Shan Shan of Tiny Toadstool.

Vertical stripes are so vaudeville, and incredibly readily available right now, so take advantage of your good timing!


L–R: High-Waist Suspenders Skirt, $60, ChicStar; Kelly-Marie Burdekin of A Harem of Peacocks; Georgina of Cupcake’s Clothes.

I love how opulent and dramatic velvet can be.


L–R: Hello Sunshine Dress, $65, Ashley Nell Tipton; ruffle-collar dress, $40, FabULoUs Vintage on eBay; Moona Saul.

Kids can usually get away with dressing way more inventively than most adults, so children’s clothing is a big inspiration for me. Cute dresses with collars are great for when you want to borrow some of the playfulness and freedom with which a first-grader regards their wardrobe.


L-R: Belles of Ireland coat, $70, ModCloth; Gretel Coat, $270, Collectif; swing coat, $144, SwingCoat on Etsy; Nicole Eymard of Fashion Forestry.

I rely on an outrageous, flamboyant coat to ensure I’ll be noticed in cooler weather.

And now for the most important part: accessories! Essential for grabbing people’s attention and NEVER LETTING GO.


L–R: Custom-made hat by Behida Dolic; Olney straw boater, $92, Tails of the Unexpected on eBay; 1940s felt hat, $39, Frocks ’n’ Frills Vintage on Etsy.

First you’re gonna need some hats. Most of the best eccentric dressers have a whole wardrobe of them.

L–R: Yours truly, Dents.

Top: Yours truly! Bottom: Gloves by Dents (red leather with ruffles and bow, $69; mustard leather, $65).

Dents, in my opinion, makes the best gloves.

Flappergirl; the Pineneedle Collective.

L–R: Women’s neck ties with lace flowers ($20.50) and with cats and polka-dots ($18.50) from Flapper Girl on Etsy; Annika of The Pineneedle Collective.

If you’re getting tired of your Peter Pan collars, try something new, like an ascot tie!

Teja Jamilla, Sockdreams, The Pineneedle Collective.

L-R: Hand-painted Art Nouveau Printed Tights, $26.50, Teja Jamilla on Etsy; Floral Flocked Tights, $12, Sockdreams; Annika of The Pineneedle Collective.

I love a good pair of embellished/printed/generally awesome tights. Teja Jamilla’s store on Etsy stocks beautiful tights that go up to a (U.S.) size 28! Sockdreams has a plus-size section—and I find that their straight-range sizes run really big.

Rachel Antonoff for Bass, Chie Mihara.

L-R: Bass ♥ Rachel Antonoff Women’s Snim Lace-Ups, $83 for similar, Zappos; Tamer oxford ($465.50) and Isias Navy flats ($360), Chie Mihara.

I’m always one for a mannish shoe, so I’m a big fan of Rachel Antonoff’s line for Bass shoes. Chie Mihara, too.

Alice Takes a Trip, Miss Patina.

Hello Sailor Dress, $89, Alice Takes a Trip; Oktoberfest dress, $70.50, Miss Patina.

Special mentions: Alice Takes a Trip and Miss Patina are two of my favorite independent designers when it comes to no-holds-barred style with a vintage flavor.

Nouveau Suede mask in Imperial Purple, Face Lace.

Nouveau Suede mask in Imperial Purple, $28, Face Lace.

And finally, if you want to pull out all the stops, here’s some Face Lace.

Have fun dressing up! ♦