Ask a Real Teen: Shopping & Personal Style

A high school freshman reflects on cool kids, hypebeasts and current trends

I've long been fascinated by teen culture. When I was a teenager myself, I was trying to recreate experiences I'd seen in movies like Dazed and Confused or read about in Perks of Being a Wallflower. It's been eight years since I've graduated from high school, but I still enjoy consuming media about the teenage experience. Maybe it's because we all feel a bit like an outsider. Or maybe every decision we make as adults, consciously or not, is made to avenge our teenage selves. Just me? OK.

I have a teenage sister who just entered high school—the very same high school that I attended. And though I have no interest in reliving my high school years through her, having her as a connection to that strange, yet wonderful stage of adolescence keeps me grounded and empathetic of teenagers in general, but also Teenage Diana.

And since I have this source into the mysterious world of teenage girls, I thought I'd take the opportunity to ask my sister Andrea her thoughts on shopping, trends and finding your personal style at a time when nothing is really yours.

How would you describe your style?
I would describe it as an extension of my personality. Yeah, yeah, of course your style is an extension of your personality, but that's all I can think of. I'm outgoing at school so I like to pick outfits that are fun or make me look approachable if people wanna become friends. My favorite outfit is my dark blue crop top paired with my high-waisted, straight leg jeans, with my old slip-on checkered Vans. Jewelry is also a giant part of my style. I always wear my ring that my older sister made me, and I love, love, love my minimalist gold chain choker.

Did you see starting high school as a chance to change your style or experiment with something new?
Of course. Everyone around you is trying to dress different to prove that their style is better than other people's. You see people trying to do this with brand new expensive brand names, you see people perfecting their shoe game, girls wearing jewelry you wish you thought of wearing first. Since there's more of a variety in style in high school, I've found myself feeling more confident in clothes that I didn't really see people wearing in middle school. I even made a Pinterest board dedicated to what I want to wear for freshman year. Your outfit is the first thing people see about you and so your sense of style is the perfect opportunity to express yourself in an environment where nobody knows who you are.

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Where do you shop the most? Online? In-store? Any favorite stores?
I shop most at H&M, in-store and online. I love it so much because the clothes are cute and they're really well priced. The jeans? They're cheap and cute! Buy a couple pairs! And if I need shirts or hoodies, they got me! The way I see it, it's better to get more clothes because it costs less money than to buy 2 sweatshirts from a certain brand and spend all the money you brought to the mall. Ballin' on a budget is always better.

Where is the coolest place to shop? The place where everyone seems to shop.
The coolest place to shop right now is definitely Brandy Melville. All of my friends shop there and their clothes are really trendy. I think it's popular because it fits so many people's aesthetics. It's also really popular because so many influencers dress in clothes like that. Emma Chamberlain is a teenage YouTuber that many girls I know look up to for her fashion and aesthetic and guess what? She shops at Brandy. The clothes there are so cute and it's really easy to find something you like yourself in. The clothes aren't "basic" and I love that anyone who wears their clothes can make them unique to their own personal style.

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What trends are you and your friends really into right now?
My friends and I love the dad hats! They're so perfect for when your hair isn't cute but you still want your outfit to be poppin', or when you just wanna look laid-back. My best friend and I are always wearing hats now and I'm so glad I decided to get some!

How do you choose what to wear in the morning? Do you plan it out ahead of time?
I usually visualize the outfit I want to wear the day before I actually wear it. It's not always successful and I usually end up trying on different shirts and stuff but it helps me save time in the morning by giving me an idea. I'm not gonna lie though, on the night before the first day of school I always lay out my clothes on my chair, shoes and everything. I love putting effort into the what I wear though because it makes me feel confident when I leave the house. If I don't feel confident, I'll be insecure and shy all day and it has an effect on my schoolwork for the day so I always try to avoid picking a bad outfit.

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What current trends do adults wear that you don't understand? What about trends teenagers are wearing that you don't understand?
I can't really think of any trends that adults are wearing that I don't understand, but I have a lot of trends that teenagers are wearing right now that I don't like. For example, the overdone '90s kid thing. Baggy colorblock shirts or crewnecks paired with baggy jeans aren't really something I would try. Another thing I don't understand are hypebeasts. It's okay to flex but just don't flex too hard because it's not cute. I respect it, but I just would never try it, plus it's a pretty expensive kind of style to have.

Do you feel pressure to keep up with trends or to be "cool"? Are there still "cool kids"? Who are they and what do they wear?
I don't feel any pressure to do anything anyone else is doing. I wear what I like and it makes me happy. There are still cool kids and people like most of them because they're genuinely really friendly and nice. The girls are wearing off the shoulder tops, a lot of Vans, and yes, PINK. I do think some of the clothes they wear are cute and when I see something cute, I take a note of it and try to incorporate into my own style.

Diana Le

Diana Le

Diana is the co-creator and Editor-in-Chief of Oatmeal Cardigan. She works as a copywriter by day and moonlights as a texting guru by night.