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How to Dress Like a Teenager Forever

Hey, I just met you, and this is crazy, but here’s my number, so…” okay, you know the rest of the song. If not, listen to Carly Rae Jepson’s instant hit here. Selena Gomez, One Direction, and Justin Beiber can make anyone born before 1993 feel old. But dressing young is not only rejuvenating, it’s fun too if you just add certain styles one piece at a time. In an extreme example, the other day I left the house dressed like a 15-year-old. Although I normally just add a few elements like bright bracelets or a pair of classic Converse sneakers.

While I don’t recommend dressing like a teen head to toe (hint hint Real Housewives of Orange County), there are elements of ‘teeny bopper’ fashion statements that are acceptable at any age. Plus they’ll bring out that teen girl in you all over again…

1. Graphic Tees & Cutoffs ~ A tee like this is perfectly acceptable with a pair of jeans as long as it’s not too short & it’s rhinestone free. Also, I might wear these shorts with a white tank and long neutral cardigan sweater with flat sandals.

2. Spiked ~ This silver Renegade Cluster Bracelet by Stella & Dot  is one of my favorite pieces of jewelry appropriate for any age. It can be worn with a bunch of bracelets, alone, or next to your favorite watch. (Comes in gold or silver)

3. Sparkly TOMS ~ It took me a while to come around to the style of TOMS, but once I tried them on, they are one of the most comfortable shoes ever. You can walk miles in TOMS and I know 2-year-olds to Elementary school teachers who wear the sparkly ones. Try pink, silver or black.
Teeny Bopper beverage ~ It’s okay to swap a Red Bull or your energy drink of choice in place of a coffee every now and then. But after I hit 25, I switched to Sugar Free.
Tourist Tip ~ If you’re ever in San Francisco, make sure you take a walk on the Embarcadero at sunset for a view of the Bay Bridge. (Me walking Wallace, the CEO of The City Supply Co.)
4. Color by Numbers ~ While age is just a number, I’m not naive to the fact that I’m no spring chicken. 🙂 My days of wearing tangerine cutoffs may be limited, but I can guarantee I’ll be wearing dresses, tops, skirts and pants in whatever the hot color of the season may be for the rest of my life. (which is what I’d encourage every woman to do.)

5. Speaking of T’s ~ Men and women can wear bright t-shirts under blazers or with a  pair of jeans. This GAP building in SF lined with a ‘T’ made of tee’s on Brannon street always catches my eye

Tee ~ Project Social Tee, Watch ~ Michael Kors, shorts ~ XX1, Neon bracelets ~ courtesy of 33Knots, other bracelets ~ Forever21 & Stella & Dot, nail polish ~ Sally Hansen Insta-Dri

While I wouldn’t wear this outfit anywhere other than the beach or Disneyland, what do you think about adding a few teen styles into your outfits? 

Have a great weekend!

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  1. Melissa says:

    The shorts look great and it took e time to warm up to Toms to but there awesome for travel. I especially love that you say teeny bopper! I say it all the time and my friends love it.

  2. I went to forever 21 a few days ago and I’ve never felt sooooo old. I honestly can’t pull off crop tees and cut off shorts in neon colors. I do love TOMS and Converse. I can wear those all day.

  3. the creation of beauty is art. says:

    These are great tips for bringing a little youth into the wardrobe! I love the sparkly TOMS. My pair of TOMS are just the comfiest shoes ever!

  4. I am no spring chicken either, but I still feel so young and love to wear clothes that are meant for younger gals! I just make sure to always pair the teeny-bopper stuff with more sophisticated clothes at the same time and it still works well. I love your shorts and think you pull them off well! You look great! Hope you have a great weekend! xo



  5. GirlieBlogger@Beauty Fashion Blog Seattle says:

    Fantastic tips. No matter how much I despise drama, I just love watching the Housewives. You look fantastic in that teen getup.
    Seattle Beauty Fashion Blog

  6. Dale, I’m totally on the same page with you and rocking the teenage summer wear. If it makes you happy, I say go for it!

  7. Steph Yt. says:

    great post hun! Love all the detail you put into the steps! You definitely look really youthful in these photos! I adore the tangerine cut offs! Can’t wait to see your next post!

    Ginger and Lace


    hahaha well im a ‘teen’ and personnally i dont think people should really try to forever dress like a teen, its just kind of weird in my opinion…

  9. Lotus Blossom Design says:

    You’re in great shape so those teeny bopper shorts look phenom on you! Great tips.

  10. Kitchen Beauty Benefits says:

    lol i loved this post!! especially the spring chicken line! n darn, you cud give any teen a run for her money! M certain some cute teen boys must be crushin on you! 😀


    Gorgeous outfit, love the details. The bracelets are very pretty 🙂

    – Malena

  13. Nice pictures 🙂
    I love your bracelets, especially the spiked one!!

    xx Timna

  14. Dominika says:

    I can’t stand it when people think that adults can’t dress like teenagers from time to time. In my opinion, it looks great provided that the person doesn’t overkill. You’re living proof that adults can pull off the whole teenage look, you look amazing 🙂


  15. Lovely tips 😀

    With love,Mia

  16. I think t-shirt and shorts can look good at almost any age (if you have the legs to wear shorts xD)

  17. A Blog With Us says:

    Really nice post, love how you look in this outfit, now following your lovely blog, maybe you can check mine’s and follow back if you like it http://ablogwithus.com

  18. Hi Dale,

    So…Call me, maybe? Such a catchy song. As for the outfit. Simple,fresh and young…but it’s good. I too feel we should dress for our age. The days of Hollister and A&F were retired years ago for me…I recently saw an elderly woman, and by elderly I mean somewhere in her mid 50’s or early 60’s? Wearing a Hollister T. Not so good. I am loving the new trends with all the bright colors and color blocking…can say I haven’t purchased any bright colored shorts…although I did get a pair of bright colored skinny jeans…and love them. With that said…I say YES! A pinch of teen flare keeps the heart young. Great post. Have a wonderful weekend.


    • Yes, that’s so true Lola and I definitely haven’t been in an American Eagle, Hollister or AF in years 🙂 I love that your wearing the skinny bright jeans, I’m loving them too!


  19. fleurani says:

    Dale, great post. I am no spring chicken either turned 30 last year, but I still feel and look so young and love to wear clothes that are meant for younger girls! I just make sure to always pair the teeny clothes with more sophisticated/elegant clothes and it works so well. I will never get tired of bright colours doens’t matter how old I will get. You pull the shorts off so well, looking really good!

    Have a wonderful weekend lovely Dale 🙂



  20. Brandon Lostinidaho says:

    Teen girls? Cute. Teen guys? Mostly awkward, or trying too hard.

    Guys don’t find good fashion until their early 20’s, at the soonest. I think I’ll stick to Gen-Y instead of Gen-TXT

  21. Great outfit, love the sparkly TOMS!!

    Diary of a Short Girl

  22. I love your look… its always fun to add something bright or teen-y to your look!

  23. Shes Dressing Up says:

    Such a fun post, love it! Gorgeous photos too 🙂

  24. Elegantesque says:

    you look very cute like this !



    clinique giveaway
    Elegantesque Blog

  25. leonie fanning says:

    wow dale u look fantastic. great photos. id love to visit san francisco one day. great post kisses from Dublin xx leonie.

  26. Clara Turbay says:

    it´s great!

  27. Lovely post! I feel I totally still dress like teenagers, but no shame, I’m only 22 after all ;D I will definitely hold on to these tips later in life as well 🙂 xoxo ♥

  28. Great post! I watched these photos for a long time!))

  29. Vanessa says:

    Your blog is amazing, such an inspiration. Hope you pass by and follow me or we can follow each other.

    xo, Vanessa

  30. Vale ♥ says:

    This post is amazing, loved it, what a fun and original idea ! Dale, you look awesome in this look and you make me wanna take a flight to San Francisco right now – it must be so beautiful ! I am not spring chicken either but I like to wear “young” clothes, of course without looking ridiculous ! I hate it when some people say that once you hit a certain age you must always dress like an “adult” which means for them to dress in a dull and serious way. We don’t have to avoid trendy colors or fun t-shirts, not at all ! You gave everyone great tips here ! Kisses

    Fashion and Cookies

  31. Alisa Marie says:

    Very cute! I love the orange shorts, you look adorable!!


  32. Kayleigh says:

    😀 I love this and so true,I never want to grow up,thanks for the tips and inspiration of how to dress like a teenager and look chic all at the same time.I love the whole outfit but I especially love your arm candy! Stacked up bracelets all the way.
    Following your fab blog,hope you have a lovely day x

  33. Aurelia (A Pretty Life) says:

    wow you look pretty, It’s my dream to go to San Francisco. I have been many times on the East Coast of the United States, but never West Cost.have a nice week

  34. Couture Carrie says:

    Fun tips!
    Love the sparkly Toms!


  35. Great outfit! Love these photos! 🙂


  36. Eimear O'Reilly says:

    Love looking at blogs from america, i am travelling around the US and Canada starting from October and can’t wait to visit all these places!! love the post by the way!!

    if you get a sec, ill have a new outfit post up ina few, if you could check it out, thanks

    Eimear x


  37. LILLIAN says:

    Love your blog and all of the amazing trendy tips you give!
    You can never be too old to bring out your inner teenage years and add some youthfulness to your outfits!

    You look amazing!
    xoxo Lil

  38. fun post!! brings back so memories, haha 😛 I recently got a pair of these shoes in white lace and they are super comfy!!


  39. your bracelets are sooooo cute! love them 😀


  40. Amy Fashion Blog says:

    cute toms

  41. fox hunter says:

    Haha although I’m 16 I enjoyed reading this! I wouldn’t wear that much jewellery but ur look is cool 🙂 And I think I seriously need to buy a pair of these Toms, they seem to be so comfortable! Well I wouldn’t choose sparkling ones cause this isn’t me but I guess there’re normal ones too x

  42. B Allen @ What2Wear says:

    I love this outfit for many reasons…..but the renegade cluster bracelet is my fave…I’m a Stella & Dot stylist so I’m kind of obsessed with the whole renegade collection……love that you featured it 🙂
    Brooke @ what2wear

  43. hah, such a cute post. embrace the guilty pleasures- love it. I’m a sucker for pop summer radio too…

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