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Real-Life Style Challenge: Dressing by the Decades



Like we always say here at CF, fashion is cyclical – trends are always coming around again, so whenever you need inspiration, you can always look to the past. That’s exactly what I did this this week: Feeling like I was out of ideas for a new Real-Life Style Challenge, I cracked open the history books, and gained inspiration from the trends of decades past.

The Challenge:

This week’s challenge was really simple – and really fun! Taking a page from the fashion history books, my challenge was to create five different modern-day looks, each inspired by a different 20th century decade.

The Results:

Style Challenge- Dressing by the Decades

  • Monday – 1920s: The 1920s weren’t all flapper dresses and cloche hats. Going for a ’20s day-wear look with a modern twist, I wore a loose shirt with a floppy bow tie over a pencil skirt, tights and black booties.
  • Tuesday – 1940s: Channeling Rosie the Riveter, I paired a chambray shirt with jeans and oxfords. Not having a scarf to wear as a headband, I put on a turban instead!
  • Wednesday – 1950s: For a simple 1950s housewife look, I wore a blue A- line dress with simple oxford heels.
  • Thursday – 1970s: For a modern take on the ’70s bohemian look, I wore a burnt orange skirt with a plain black shirt and a large emerald green fedora.
  • Friday – 1990s: Channeling the ’90s grunge aesthetic, I threw on a red plaid shirt and an army jacket over a black tee. I then finished the look with a slouchy gray beanie and brown boots.

What I Learned:

We all may have a picture in our minds of what the trends were in each decade, but it can be easy to forget the simple things. A quick internet search, plus a look at our basic fashion history lesson, can help you get some retro style inspiration that’s beyond the stereotypical. For instance, I had forgotten how many ways you can define 1960s fashion – there’s Mad Men chic, Twiggy’s mod look, and the boho hippie movement, just for starters.

Once I had taken my refresher course, the rest was easy! Designers are always recycling old looks, so even in my own closet, it was easy to spot pieces inspired by the trends of the past.

A few more tips I picked up from this challenge:

  • Costumes are for Halloween. Your looks for any other day of the year should be inspired. For instance, I decided that wearing a flapper dress to a day of classes was a no-go. But I remembered that girls didn’t wear flapper dresses all day long – with a quick Google, I found pictures of 1920s day wear and made it my own!
  • The keys to this challenge are interpreting the looks of the past, and incorporating trends from each decade into your personal style. I knew that I was not dressing in genuine grunge or 1970s bohemian attire – instead, I was making those old looks my own.
  • Beauty changed over time as well! Though I didn’t have the opportunity to play with makeup or hair for this challenge, it could be be fun to try a mod bold eyeliner look from the ’60s or finger waves from the 1920s. (See our series, Beauty by the Decade for detailed instructions on each.)

What do you think?

What’s your favorite fashion decade? Do you feel like your style reflects this or is it pretty modern? Do you draw inspiration from any other times in history? Let me know in the comments!

Posted on on April 11, 2012 / Filed Under: Fashion Tips / Tags: , , , , , ,

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19 Responses to “Real-Life Style Challenge: Dressing by the Decades”

  1. 1
    April 11th, 2012 at 7:19 pm

    I always like seeing your articles. Your column is one of my favorites :)

  2. 2
    April 11th, 2012 at 7:39 pm

    Love this. I am incredibly obsessed and inspired by the past, so I think I’ll try this too. Sometimes it’s just nice to go backwards instead of forewords with trends.

  3. 3
    April 11th, 2012 at 8:40 pm

    This is so fun guys.
    When I first saw that it was a challenge, I thought maybe it’s a link up party!

    Hope you guys host a link up party, and ….I hope we don’t have to be in college to participate. :)

  4. 4
    April 11th, 2012 at 8:57 pm

    My favorite decade for fashion is the 20’s but I love your 70’s outfit!! Great style challenge!

  5. 5
    April 11th, 2012 at 8:58 pm

    Such a cute idea!

  6. 6
    April 11th, 2012 at 9:17 pm

    Love the 70s look. And the blouse is adorable in the 1st look. This is like decades day at school, except more wearable and less ridiculous.

  7. 7
    April 11th, 2012 at 9:21 pm

    This is fantastic and I love it but what about the 1930s?!

  8. 8
    April 11th, 2012 at 9:37 pm

    Your columns are my favorites! I love your fashion challenges and they really inspire me.

  9. 9
    April 11th, 2012 at 10:24 pm

    girl, i go to emerson too and i see you around ALL THE TIME. i look forward to these posts to find out what challenge you’re doing! heard you mentioning something about colored pants in an lb elevator, fingers crossed that challenge is coming up!

  10. 10
    April 11th, 2012 at 11:23 pm

    Love the 1940’s inspired look! But I would also love to see a 1930’s outfit!

  11. 11
    April 11th, 2012 at 11:23 pm

    Awesome! Great outfits and nice job on the interpretation. I think this might be the best style challenge yet!

  12. 12
    April 12th, 2012 at 1:28 am

    I don’t really see it. No offense, I just don’t think these are very inspired by the decades. I know it’s not supposed to be costumey, so you say, but i feel like there could have been more. these look like normal outfits. eh.

  13. 13
    April 12th, 2012 at 7:45 am

    I see where you got the ideas but I always think you go for pieces that don’t flatter your shape. I feel like your proportions for clothing usually shortens your torso because you wear too much high waisted things which sit just under your chest and then create a stomach that doesn’t exist rather than highlighting your waist but still emphasizing the importance of elongating your legs. I think the 1920s is the most successful just because your petite frame looks best with those proportions. The others make you look too costumey and wind up looking a little sloppy to me. I’d like to see you in some short blazers and jeans with heels to see how it elongates your body and plays with proportions.

  14. 14
    April 12th, 2012 at 10:02 am

    love these articles! keep them coming! :)

  15. 15
    April 12th, 2012 at 10:07 am

    love this! i think it’s your best challenge yet :) love every outfit

  16. 16
    April 12th, 2012 at 3:41 pm

    Love this! Keep these articles coming I especially like how these outfits all take inspiration from rather than actually copy the decades they cover. I might try the 20’s one!

  17. 17
    April 12th, 2012 at 3:41 pm

    Amazing! I love the big hat in the 1970’s one!

  18. 18
    April 12th, 2012 at 4:07 pm

    I will definitely be trying this challenge when i go back to uni! I love the orange skirt and the whole 90’s grunge look :D

  19. 19
    June 8th, 2012 at 4:30 pm

    I LOVE THESE LOOKS SOOOO MUCH!!! I love how they look like normal everyday go to class outfits without looking like costumes or by looking like u stepped into a time machine and are wearing the exact same thing back then lol. I love this I am totes gona be doing the 1950s rocking my polka dot a-line dress which I love that era and the the 1990s grunge totally loved that look felt the Kurt cobain vibe lol and I gota rock the 1920s that is tooo cute to pass up love that time period too thank u so much for these colums I always look forward to them :)

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