1. Adam Fulrath, art director
I'm 21 and in college. It's the perfect do-it-yourself haircut: Two mirrors, $12 clippers and one messy dorm bathroom.
2. Allison Williams, associate features editor
“I blame the salty sea air for this knotty hair. I was on a camping trip at Olympic Peninsula in Washington State, which is why I’m dressed like the bottom of a Value Village free bin (but with matching teddy-bear socks!). My scalp still has PTSD from the detangling experience that followed this trip; forget waterboarding, someone should send my mom and her pitiless combing skills to Gitmo.”
3. Amanda Waas, brand solutions coordinator
“Remember when you were six years old and all you wanted to do was go outside and play? Yeah, well, you can’t always get what you want. Here I was being dressed up in girly garb by my grandmother. Just look at that forced smile! My hair appears to be feathered a bit, and who doesn’t love a princess crown? While the hair is bad, what really steals the show in this Victorian nightmare is the dress. When I showed this photo to Marisa Fariña, Time Out’s group publisher, she said ‘That dress looks like you could upholster two couches with it.’ Enough said.”
4. Angela Sundstrom, assistant consumer marketing manager
“I was 26. This bleached faux-hawk of doom was not designed for outdoor use. In the privacy of my own home, I often apply hair/face masks just before playing Guitar Hero in my underwear.”
5. Andrew Toal, staff writer
“I was 27 here. TONY editor-in-chief Michael Freidson made me proposition Boyz II Men.”
6. Ashlea Halpern, senior editor
“I’m about six years old in this shot, and these were my North Carolina neighbor’s pet ducks. All things considered, I thought (and still think) my hair is pretty rock & roll. Überflat bangs, the shaggy-rounded fringe…I pulled off a chili-bowl cut long before Karen O.”
7. Beth Greenfield, Gay & Lesbian editor
“I am 18 years old in this photo, on my way to the senior prom. My style at the time was some sort of goth-punk-suburban-hybrid mess, and in this photo my hair, which I was always overspraying with Aqua Net, had been freshly frizzed with my crimping iron. I was thinking I was some sort of Siouxsie Sioux Mini-Me (not!) and, most important, that I would not look anything like the prom queen.”
8. Beth Levendis, associate photo editor
“I used to dump my girlfriend’s leftover peroxide on my head. Sometimes it looked good! But then I waited in line for three hours at the DMV for this picture. I think I was about 25.”
9. Billie Cohen, deputy editor
“I was an 11-year-old soccer jock. I guess I’d call the style a first step toward the awesomely layered, winged, hair-sprayed creation I would sport at age 13—photos of which I must’ve burned, or someone else did, because I can’t find any. This was my first (and I hesitate to use this word) hairstyle after chopping off the butt-length, stick-straight locks that I’d had since I was about six. I thought I was cool—a mistake I continue to make to this day.”
10. Colin St. John, music writer
“I hate to say it, but I think this was my birthday freshman year of college. Seems I was trying to bring some late-’90s Western grunge to all the Boston softies. That said, I get some redemption points for the Cabin Boy DVD resting on the coffeemaker.”
11. Cristina Velocci, assistant features editor
“As a clueless eight-year-old, I had no idea how to style my hair. And apparently neither did my mom, who used to brush my curls—the single most offensive thing you can do to them. My locks went from Shirley Temple–cute ringlets to Medusa-like kinks of frizz and fury in a single brushstroke. And don’t even get me started about that vest.”
12. Ethan LaCroix, managing editor
“I was probably about 20 in this picture. I was in college (as if you couldn’t tell from the cement walls with the IMAGINE poster—so dorm). This was a popular late-period-grunge look and a lot of rock stars had neon-colored locks, so it was sort of trendy, at least on my campus. I did this to myself probably five times over a year or so. I also experimented with Manic Panic colors: Orange and red were favorites. Unfortunately, my hair is super dark and coarse, so it took a lot of time and peroxide to get it to the yellow color you see here. The one time I got the white-blond tone I wanted, I ended up burning the top layer of skin off my scalp and couldn’t go outside without a hat because the cold air hurt my head so much. That experience ended my affair with hair color for good.”
13. Evan Morgenstern, finance clerk
“I was 23 and was doing the good ol’-fashioned part to the side. It was late one night and my girlfriend and I had the crazy idea of dyeing our hair blond. So, we went to a 24-hour Walmart, and I bought Maxim’s hair dye for men and she got some other cheapo brand. Both of us ended up looking like we had orange hair. I dyed mine black to cover it up and she got what turned out to be a surprisingly not-terrible short haircut at Walmart the next day.”
14. Lucy Quintanilla, associate art director
This is just horrible. I begged my mother mercilessly until she broke down and let me cut bangs. At the time, I thought I was the shit; looking back I question my sanity. This is just one in a series of ultra-crappy school portraits where I rocked bangs. Needless to say, I didn't know what a flat iron or hair products were during my formative years
15. Michael Freidson, editor-in-chief
“I was 17 and snuck into an Atlantic City casino with my girlfriend, who was kind enough to tell me to stop wearing silk jackets shortly after this photo was taken. Unfortunately, she never warned me about my hair. In the salon, they called it the ‘Tom Hanks in Big.’”
16. Noelle Stout, account manager
“This was taken right before Rock of Love aired. So even though it was incredibly tacky, me and my 24 years were at least ahead of the retro-trashy curve.”
17. Raven Snook, TONY Kids Web editor
“Personally, I think my hair was fabulous in this pic. It was 1985 and I was (oy!) 14. I was a hard-core goth with a new-wave edge, thinking I was hot and cutting edge!”
18. Samantha Terry, marketing manager
“I was 12 in this photo, and actually thought it looked hot—in fact, I had just come back from the hairdresser!”
19. Scott Wooledge, special projects designer
“I wanted to be George Michael circa Wham! in this photo. But I was 17! I plead ignorance and blame it on the fog of the ’80s!”