Don’t get me wrong—moms know a lot. They’re freakishly good at multi-tasking, and they have an extraordinary ability to ask “ W hat’s wrong?” before you even realize you’re upset. But let me ask you this: would you let your mom choose your prom dress for you? Your wedding dress? Your lipstick color? If the answer is yes, then cheers to you for having come into this world through the birth canal of Carine Roitfeld. On the topic of style, mom does not always know best. Then again, neither do you. Which is when, of course, moms can fairly say, “I told you so.”

I remember the first time I thought, “Maybe mom doesn’t know best.” I was five, at an uncle’s wedding in Ohio, and I was sobbing hysterically behind a couch because my mom had dressed my three-year-old brother and me in matching plaid rompers (it could have been a dress but, for all intents and purposes, it was a romper) that had our names down the front next to huge felt duck decals. We may share the same chromosomes, my mom and I, but we have never shared the same sartorial outlook. The above scenario withstanding, we got along OK in the personal-style department...until I began to understand the concept of “cool”—that was on the ride home from seeing Clueless in 1995. I was ten and, though I didn’t know what it meant to crave an “herbal refreshment,” I could infer that the Laura Ashley twinset I wore to the theater would probably not land me at a lunch table with Cher Horowitz. And so it came to pass that on my first day of sixth grade at a conservative Connecticut middle school, I donned a plaid miniskirt, over-the-knee socks, high-heeled loafers, and god knows what shirt. Throughout my tweens and teens, my mom and I would fight, for sure, but in the end, she always let me go for it. Brassy blond highlights? I’ll drive you, but I’m not paying for it, and it’s going to look weird. Blue contact lenses? Fine, but I’m telling you, your real brown eyes are nicer... Maybe there was some of that psychic-mom thing going on, where she knew that my fashion and makeup obsession and all of the experimentation was going somewhere.

But as Mother’s Day, the most glorious of manufactured holidays, nears (May 12!!), we’d like to take a moment to acknowledge those major “I told you so” moments. Times when, if we could go back, we would have listened to mom.

DO NOT PLUCK YOUR EYEBROWS. Just don’t. Your brain is not capable of making smart decisions about several things as a teenager, eyebrow shape being one of them. You will over-pluck, especially in the middle, and it will take years (if that) for those barren patches to sprout again. If you’re naturally erring on the side of unibrow—and most of us have a little somethin’-somethin’ in that department—here’s a thought: let your mom help you. She has more experience with a pair of tweezers than you do.

DO NOT PIERCE YOUR BELLY BUTTON. This is probably not still applicable, given that it’s not the early aughts and “Hit Me Baby One More Time” isn’t every other song on the radio, but I always wished I had known that belly-button piercings leave their mark long after the cubic-zirconia-topped barbell comes out. And I can only imagine how that hole-on-a-hole is going to look when (one day) it’s stretched taught over a developing baby. This “wait!” philosophy can also be applied to tattoos; that’s one place where my mom stood her ground.

And now, a male perspective (courtesy of Mr. Nick Axelrod):

I wasn’t a particularly eccentric kid—I didn’t go through a Juggalo phase; only one pair of Jncos—but I always had a particular and, in retrospect, pretty homosexual sense of style. A flair for vibrant color (the neon spectrum, tie-dye), an appreciation for vests, a bizarre (but I think totally acceptable at the time?) investment in biker-shorts-as-pants. But the area in which I came closest to reaching the limits of my parents’ lovingly blasé attitude was my hair. Every so often, usually at home over the holidays, I’ll uncover a photo of myself with, maybe, henna-dyed brick-red spikes (age 10) and my mom will glance at it and say, “That was really horrible.”

Why’d you let me do it? I didn’t drive myself to the natural-food store to buy the henna, and I certainly didn’t use my non-existent income to fund this ongoing dyeing habit. Her answer is always, “Well, you wanted to do it.” This is what’s so cool about Gwenn, my mom. But also, GWENN, WTF!? How could you let your son look like a damn fool??

When Emily and I decided to pay tribute to our very understanding mothers for this post, I emailed mine to ask her how she coped with my style quirks, and also to get her side of the story regarding my most egregious hairstyle [photo 4]. The story involves a bowl cut, a beauty parlor called “Tress?” a chain-smoking stylist, five hours of bleaching (applied to only the ‘bowl’; the sides remained my natural dark-brown), and an amount of parental love and support I’m not sure I’ll ever be capable of generating in this tiny, bike-shorts-loving heart of mine.

“You were very insistent about bleaching your hair—the word ‘relentless’ comes to mind,” my mom said. “Dad and I just figured, whatever, hair grows back. So, we took you to the local beauty salon and Meryl did it. It took literally hours to bleach your hair; the cut was faster. What a look… It seemed to mean something to you, though, and it wasn’t harmful, so we didn’t care. Also, you’d have to figure out how to deal with the assholes who looked at you and made comments... I have no idea where you got the idea from—Andy Warhol?

“You always had very specific taste in clothing,” she continued, “and seemed to always have an image in your mind about how you wanted to look. Unfortunately, your image did not match the image I had in my mind. Before you were born, I imagined a Jewish ‘John-John’ (John F. Kennedy, Jr.)—sort of WASPY PREPPY, little navy shorts, tennis sweaters, little ties, little navy blazers, maybe chinos…But, we let you choose your clothes as soon as you wanted to. You wore Oshkosh and t-shirts for years and years and liked turquoise and dark purple. But when you bleached your hair, people would say, ‘How could you let him do that?’ You got a lot of stares. I think it only lasted for that summer—I know for your Bar Mitzvah it was back to brown. I guess our philosophy was that you could choose whatever you want to wear and how you wanted to look. If you wanted to wear something and you felt good about how you looked, we were fine.”

I recently tested this philosophy when this story went up on ITG. “I have no words,” my mom said. Fair enough.

Well, here’s a thought!

This Mother’s Day, don’t just send a card, email, or text with thirteen heart Emojis. Acknowledge how, and when, your mom knew best—at the very least, you’ll laugh about it. Or better yet: go shopping. Take HER shopping. Which is where Barneys New York comes in. We’re teaming up with the retailer to give away two $1,500 Barneys gift cards , which is certainly enough cash make both you and your madre happy. Who knows, she could, as it turns out, ultimately be the Cher to your Tai. Or, at least she’ll make sure you don’t look like a farmer in those clothes.

** Note: Contest has ended. Thanks to all who entered! Winners will be notified soon.*

—Emily Weiss and Nick Axelrod