Day 1
I begin with a classic updo, gathering up all my hair and then twisting it into a ballerina bun (sported by many an off-duty model). My hair isn't quite long enough to make a big knot, and I end up with more of a nubbin. Nonetheless, it feels refined yet casual: the perfect day-to-night do.
TIME : 4 minutes (washing and drying time not included)
TOOLS : Frédéric Fekkai Sheer Hold hairspray, elastic band, bobby pins
Day 2
I keep my second look as simple as the first (I have to ease into this thing!) and try a Whitney Port–like middle part with twisted and pinned front sections. The look is very functional—my hair is down, but my forevergrowing- out fringe is out of my face. A compulsive hairtoucher, now I have nothing to do with my hands while talking except gesture wildly. I make fists instead.
TIME : 2 minutes
TOOLS : Bobby pins
Day 3
To impersonate primping princess Blair Waldorf , I set my hair in hot rollers before placing the headband/crown. I may have pulled this off too well—I'm pretty sure I hear some prepschool girls gossiping about me on the subway. Wannabes.
TIME : 20 minutes
TOOLS : Revlon Ionic Hairsetter, Goody headband, Tigi Catwalk Your Highness hairspray
Day 4
Yesterday's curls still intact, I rough them up with a little dry shampoo and pin them into a disheveled French twist . Topped off with a headband, the effect is fetchingly Grecian. I plan a toga party.
TIME : 5 minutes
TOOLS : Teeny House Bunny Priscilla Headband, Klorane Dry Shampoo, bobby pins
Day 5
I continue my headband fixation with this punk take on a '30s turban : Who needs mace when you have an adorable hair accessory that doubles as a weapon? This plan backfires when I inadvertently injure myself (just a scratch) while removing the artillery.
TIME : 4 minutes
TOOLS : Jennifer Behr Spiked Turban Headwrap, elastic band
Day 6
Inspired by a red-carpet photo of my celebrity pretend best friend, Drew Barrymore, I ask stylist Pasquale Ferrante to craft a hippie-chic, braided updo . I would wear my hair like this every day if I could—it's soft, sophisticated, and even a strong wind couldn't shake it out of place. It's my new go-to for special events.
TIME : 30 minutes
TOOLS : Pasquale Ferrante at Ion Studio, NYC
Day 7
I whip out the hot rollers again to create a '40s-inspired wave . I roll the front section back (it only takes four rollers to cover the rest of my hair), and when I pull out the roller, my bangs form a perfect ringlet. All I have to do is pin it. My hair was made for this era!
TIME : 20 minutes
TOOLS : Revlon Ionic Hairsetter, Frédéric Fekkai Sheer Hold hairspray, bobby pins
Day 8
Tempted to rock the celeb-beloved bob , I create a surprisingly simple faux version— no scissors required. I pull my hair back into a low ponytail and pin it under. My friend calls it "librarian-meets-suffragette." I won't be marching anytime soon, though—the bobby pins don't feel secure, and I could be revealed as a crop-imposter at any moment!
TIME : 10 minutes
TOOLS : Elastic band, bobby pins
Day 9
Designers such as Karl Lagerfeld and Diane von Furstenberg welcomed crimped hair back to the runway. Why shouldn't I revisit the style I aced as a kid? Sadly, I think I look more like Tarzan after too much jungle juice; over drinks, my friend asks if I've been licking electrical sockets again.
TIME : 20 minutes
TOOLS : Hot Tools Helix Crimper Kit, Redken Spray Starch
Day 10
Crimping, I realize, works much better with a little discipline. Pulled back into a geometric updo , it even garners a compliment from a complete stranger (a stylish Brit girl), the true test of an experimental style.
TIME: 4 minutes
TOOLS : Bobby pins, Tigi Catwalk Your Highness hairspray
Day 11
I rarely feel sophisticated, but these Lauren Bacall–like waves change that fast. After setting my hair in rollers, I brush out the curls and apply styling cream for extra silky strands, then pin one side back. It's simple to create yet feels siren-chic.
TIME : 25 minutes
TOOLS : Revlon Ionic Hairsetter, Philip B. Crème of the Crop Lite, bobby pins
Day 12
Hairstylist Julien d'Ys somehow made dime-store-comb headbands look luxe at YSL's spring show, so I try to do thesame, fitting six of the gold, silver, and black bands on my head (d'Ys used 10–15). It looks exquisite, but now I see why models make the big bucks: Within five minutes, I succumb to cranial discomfort. Get these things off my head!
TIME : 15 minutes
TOOLS : Scünci Stretch Combs, bobby pins
Day 13
Nothing makes me feel more badass than a good old-fashioned, Elvis-worthy pompadour . After teasing and spraying the front section of my hair, I pin it back and shellac it with even more hairspray, then secure the back section into a tight twist. Tonight, we rumble.
TIME : 10 minutes
TOOLS : Tigi Catwalk Your Highness hairspray, Ricky's comb, bobby pins
Day 14
I've never had sexy, Rapunzel-length hair , so I seize this opportunity to live the lush locked life and try out extensions. I can't help but be reminded, though, of DJ Kool's '90s dance anthem "Let Me Clear My Throat," in which he asks the ladies in the house to "make some noise" if they have real fingernails and real hair. For the first time, I'd be the girl on the floor not making a peep! Eh. Who cares? This hair is fabulous!
TIME : 15 minutes
TOOLS : Ted Gibson Clip-in Extensions
Day 15
The superlong side-braid at Alexander Wang's spring show is an office sensation: I unabashedly turn to extensions again. On me, the look is less downtown, more out of town—as in, on a farm.
TIME : 20 minutes
TOOLS : Ted Gibson Clip-in Extensions, Sachajuan Ocean Mist, elastic band
Day 16
Now that I've accumulated a mountain of bobby pins (yoo-hoo, MacGyver), I lay down a full set on one side of my head (another recurring runway look). I think I'm picking up cell phone signals.
TIME : 3 minutes
TOOLS : Goody Colour- Collection bobby pins
Day 17
This extremely large headwrap (from DVF's resort runway) would be perfect for a hipster Kentucky Derby. In lieu of this, I wear it to a party at a Manhattan sports bar, where my friend informs me that I look like a puppy wrapped up in a bow. Grrr. I think it's Desperately Seeking Susan–superb.
TIME : 2 minutes
TOOLS : Diane von Furstenberg printed headbow
Day 18
VERDICT : Stylist Paul Labrecque helps me channel material girls Marilyn and Madonna with full, controlled ringlets . I love the bounce, but now I look exactly like my mom's driver's license photo circa 1987.
TIME : 30 minutes
TOOLS : Paul Labrecque, NYC
Day 19
I stole this idea from an employee at NYC beauty emporium Ricky's, who told me the secret to her awesome faux-hawk was actually a long, hidden banana clip. I tease out yesterday's curls and brush up the sides of my hair before snapping it into the clip. A few bobby pins keep my wild hairs in place, resulting in a girl-meets-punk style ready-made for Rihanna. And me.
TIME : 15 minutes
TOOLS : Scünci Banana Clip, Tigi Catwalk Your Highness hairspray, bobby pins
Day 20
Terrifying. My fake hair and my real hair are at war with each other.
TIME : 1 minute
TOOLS : Ken Paves Hairdo Clip-in Bangs
Day 21
It's a bit belated, but I finally taste teenage rebellion. In my final look—pink, purple, and blue streaks —I'm staying out way past curfew tonight.
TIME : 25 minutes
TOOLS : Manic Panic and Stargazer color gels
