Go Ahead, Dress Like A Teenager In Your Thirties (and Beyond)

The older you get the more you need to dress like a teenager.

Sounds crazy, right? How many times have you heard, “Dress your age”? Or been cautioned against being “mutton dressed like a lamb”? Lies, all of it. Done properly, dressing like a teenager can be rejuvenating and a relief. In today’s post, I’m going to tell you why and a give you a list of tips to get you started.

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First, What Exactly Do You Mean By Dressing Like A Teenager?Happy Ivy 660 | Gratisography

Okay, here's the thing. I like reading books and articles on dressing chic like a Frenchwoman, building a capsule wardrobe of neutrals, and buying a professional wardrobe. I’ll even purge my closet and go on a clothing diet in lines with their recommendations. But I always end up frustrated because, for me, it’s boring! Stifling!

Do you remember how exciting it was getting dressed when you were 13? 15? 19?

How you passionately put together outfits, spending way too much time deciding just what little touch to add to fit whatever identity you had taken on for the moment? That feeling of recognition when you got it just right and you saw your true self staring back at you in the mirror? Do you miss it?

Well, why let teenagers have all the fun?

You’ve put in the years, you deserve to enjoy getting dressed even more than you did back then. There’s nothing wrong with dressing like your inner teen in your thirties (and far, far beyond).

How to dress like a teenager in your thirties and get it right: Do your homeworkHappiness Magnified | Gratisography

♠ Pinpoint something you wore that gave you a rush
Was it that top you wore to your first concert? The earrings you wore to your evening shift at the pizza place? The skirt and cardigan you wore volunteering overseas? The boots you paired with your school uniform? Your school uniform itself?

Something may pop into your mind right away. Or maybe you’ll need to look at some old pictures or in a journal to trigger your memory. Take your time.

♠ Analyze why you still love it
Is it the texture, the color, the shape, or the way an entire outfit went together? Pick two or three features and keep them in mind.

♠ Do your research
Check out a few blogs and online magazines like So What to TwentyMan RepellerMy Curves & CurlsRookie, and Refinery 29.

Think back to TV shows you watched in your younger days. Find out where the cast's clothes were sourced and study how the looks are put together. Two quick picks: The kids of My So-Called Life (click here for a breakdown of Angela’s style and here for Style Rookie's analysis of Rayanne Graff's looks) and the ladies of the Cosby Show (click here for Denise Huxtable's sartorial choices and here for lessons learned from all The Cosby Show women).

♠ Don’t be afraid to Pinterest
Pinterest is a great resource and tool for gathering ideas and inspiration. Create a board, public or private, and pin your online finds. Use the similar pins feature to immerse yourself in almost every possible way to wear something.

If you’re drawing a blank on how to put together your new look, copy, copy, copy until you’re ready to put your own twist on it. Hey, you did it as a teenager, you can do it now!

A Guide to Dressing Like a Teenager in Your Thirties: Pull Yourself Together in 5 StepsBright & Happy | Gratisography

  1. Focus on evolving, not devolving
    It’s the teen spirit you want to embody, not the body of the teen, so there's no need to replicate the exact look. If you must, be meticulous about the fit of the clothes, making sure they work with your no-longer-teenage body. Otherwise, mix it up. Look for a leather satchel instead of a leather vest, polka-dot socks instead of a polka-dot skirt, a huge satin-covered bead necklace instead of satin leggings.
  2. Take a look in your closet
    Start with what you have already. Is your past life whispering to you through a belt or scarf you’ve stashed away? Perhaps the color that is inspiring you is hiding in a pattern of a coat or sweater you own.
  3. Head to the stores (online and off) and go hi-lo
    Now that you’re ready to shop, hit up your local Goodwill, Bargain World, Dollar Store, and online boutiques like Adored Vintage and Of A Kind. Zara's always an option, too! Combine unique, well-made garments, castoff fast-fashion pieces, and anything you pulled from your existing wardrobe. For extra teen (and green) points, upcycle or refashion (check out Refashioned for an inspiring look at 46 international designers who work with reused materials ) your thrift store purchases.
  4. Don’t get precious, loosen up and wear something 'tacky'
    Right about now, you may find yourself slipping back into your grown up shell. Fight the urge and give a shout-out to your inner teen with a velvet choker, pull on a pair of black or floral Doc Martens, sport a wristful of jelly bracelets or a candy heart necklace. I love Melissa Shoes' sweet-smelling, modern take on jelly shoes.
A Few More Fun Resources to Bring Out the Teenager in You
♥ Advanced Style - New York-based Ari Seth Cohen documents elder street style all over the world, showing there is no age limit on expressing oneself boldly through fashion. As one of his muses, Linda Rodin, says, "Old is the new black." Ari has written several books and filmed a documentary called Advanced Style.
♥ Ephemera - Sheila, a 40-something poet and voracious reader, has been posting her quirky outfits of the day since 2008.
♥ Garance Doré - On her eponymous blog, Garance showcases her own sleek style along with women of all ages. Though some of her book, Love, Style, Life leans towards the must-have wardrobe essentials, Garance is a big proponent of finding your own style.
Not Dressed As Lamb - Catherine Summers opposes the term "age-appropriate" and encourages "occasion-appropriate" dress.
Refinery 29's gorgeous book Style Stalking is a must-read for anyone searching for a fun way to express their inner teenager. My favorite parts are Brights, Ladylike, Ugly Pretty (love that term!), and Metallics.
Do you know anyone in their thirties (and beyond) who dresses like a teen and pulls it off?
If you know anyone online or in real life who does it well please let me know in the comments down below. I’d love to hear about them.  Also, if you have any tips or have written a post about this topic, feel free to leave your thoughts and a link.

Photo Credits: Gratisography