8 Hideous And Cringe-Worthy Rookie Lesbian Fashion Mistakes I Made In My 20s

You need to earn the right to wear the power lesbian blazer.

Photo by istock

I’ve been gay AF since I came spiraling out of the womb in 1986, but sweet-baby-Jesus did it take me some time to come into my raging dykeness. When I first came out I had a major, debilitating, all-consuming fashion identity crisis. I was a girly-girl. What the mature lezzies call a “lipstick lesbian.” What the kids call a “hard femme.”

I’ve been wearing six-inch-platforms, daily, since the seventh grade, and I don’t leave the house without approximately ten thousand pounds of makeup adhered to my face (yes, I’m one of those wildly vain bitches who wears blush to the gym).

“Are you gay? You don’t look gay.” Some snarky lezzie said to me at my first ever lesbian party.

“Yes, I’m gay.” I said, tugging nervously at the hemline of my too-short silver miniskirt.

She stared at me accusingly and walked away. She started hitting on a girl with a snapback and skinny jeans on. I don’t look great in snapbacks or skinny jeans. What was I to do? I wanted to be visible, but I couldn’t quite pull off the whole “lesbian fashion” thang. (Most of all, I wanted to get laid. And the mean girl who told me I didn’t “look gay” was really hot, too).

So I went through an awkward phase, to say the least, babes. I made some “rookie lesbian fashion mistakes” that I still see “rookie lesbians” making all the time. So I’m going to save you all from terrible wardrobe choices, by exposing my humiliating mistakes.

1. Flannel recklessly wrapped around my waist for no good reason

Like most lesbians, I look fabulous in flannel. It’s in my genetic makeup as a raging dyke to look gorgeous in flannel. However, it’s not necessary to wrap a flannel around your waist ALL the time. It works with distressed denim. It works with sexy grunge chic slip dresses. It works with slutty short shorts (“denim underwear” I like to call them) because the flannel takes the edge off of their blatant sluttiness.

It does not work with the following: Chic white jeans. Spandex. Dress pants.

So baby gays here is an official PSA from your lesbian big sister: You do not need to prove your gayness by recklessly throwing a flannel around your waist when it’s not necessary. There is a time and a place for flannel. Don’t make the mistakes I made, because then, like me, you’ll have years of embarrassing pictures you can’t post on Facebook because you thought it was a good idea to pair flannel with shiny black leggings (true story).

2. The haircut that didn’t quite work

I’m not dogging on short hair. I love women with short hair. Pink is my celebrity crush after all.

However. I personally identify as a Lesbian Mermaid, and we all know Mermaids of sexual orientations don’t look good with short hair. We need long, flowing, blue-green hair, or else our scales look too exposed and vulnerable.

When I came out, I had one of those half-assed lesbian haircuts (I was too wimpy to really go for it, it was a hideous Lisa Rinna style bob).

PSA from your lesbian big sister: IF you want to cut your hair because you’ve always wanted short hair and your gayness is only amplifying your desire for short hair, do it. IF you want to remain a Mermaid, stay a Mermaid you cute little lesbian Mermbabe.

3. The impulsive tattoo

“I came out of the closet so I’m going to get drunk with my new lesbian crew and we’re all going to get tattoos that we’re going to regret when we’re 31 and have poorly inked symbols that mean absolutely nothing etched onto our arms for life!”

4. Wild insecurity

I’m still completely and totally intimidated by every pretty, tough, or wealthy (what? I have class issues, sue me) lesbian I meet. We’re a rough crowd! We’re hard on each other, we call each other out in the harshest of ways on the internet, we give each other dirty looks in bars if we accidentally glance at each other’s girlfriends, and we can swing a hammer better than any fuckboy in every red state ever could.

Even though I’m still seeping with irrepressible shyness, I’m not insecure around my own kind anymore. I’ve learned that even though we’re tough bitches on the outside, we’re sweet little Cadbury Cream Eggs on the inside. When I wore my wild insecurity on my sleeve it was a major fashion faux-pas. It made everything I wore look like a uniform. An uncomfortable school uniform you’re forced to wear and feel completely and ugly and stupid in.

PSA from your lesbian big sister: Queer Kittens. If you’re not comfortable in your own skin, everything you wear will look ridiculous. However, when you finally accept yourself, you can get away with wearing anything your gay little heart desires. Like bras as shirts. I do it all the time, and no one fucks with me (At least in person).

5. A frown


Just because you came out of the closet doesn’t mean you can’t smile anymore! I understand that the world is falling apart and lesbians are supposed to be very SERIOUS creatures WHO DON’T HAVE FUN, but FROWNING all the time will only give you wrinkles. Which are not cute. Like, ever.

However, if you’re incessantly frowning, I know of a really good top secret lesbian Botox party that happens in the West Village every three months. PM me, I’ll  give you the deets, dahling. (For the record, I haven’t done Botox YET, but I will be doing it soon. I’ve only injected my lips, which I highly recommend to anyone who wants to look overtly sexual all the time).

6. The lesbian blazer I wasn’t quite ready for

You have to earn the lesbian blazer. You can’t just pop one on when you’re not ready to possess all the power it commands.

7. A sports bra as a shirt

I thought crop tops were too “girly” but I still wanted to dress like a slooze, so I rocked sports bras, as shirts. And I wonder why I was banned in my early twenties from almost every bar in Williamsburg (that and I was, once-upon-a-time a rowdy drinker. I’m a “civilized” champagne girl now).

8. Depression

Untreated depression is not a good look. It doesn’t make you physically ugly, it makes you direly unhappy and when you’re direly unhappy you tend to fall into the shadows of the bar, attract energy vampires, and self-medicate with drugs and alcohol (which is not good for the under-eye bags).

In my early 20s, after a major mental breakdown that involved the hallucination of dogs (saving that story for my memoir, hunnies) I was diagnosed with depression, anxiety, panic disorder, eating disorder and obsessive-compulsive-disorder—it was a real party. I went on meds (Lexapro at the time, now I’m on a fab cocktail of Zoloft and Wellbutrin, known in the depression-forum community as “Welloft”), started to see a therapist, dealt with my traumas and started dressing like myself.

So PSA to my depressed baby gays: You’re not alone. You don’t have to feel this way. I know this piece is supposed to be about fashion and just took a dramatic dark turn, but these things can’t be helped. Plus fashion and feelings are wildly interconnected, I think. Anyway, please see a therapist (I know they’re expensive AF, but there are great places like Callen Lorde that offer cheap services!). Don’t let your friends shame you if you need to take meds. Don’t drink yourself into the ground (alcohol is a depressant, remember). Don’t let drugs steal your light. Accept your sexuality. Find amazing friends who won’t use you, neglect you, or verbally abuse you. And live your best lesbian life, baby. Take care of your mental health, and the fashion, my chic little dykes, will come naturally.