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Four Timeless Styles That Will Never Go Out of Fashion


Timeless styles that will never go out of fashion

Turqouise is the new black, clogs are the new shoe, Alexander Wang has the new “it” bag… you have to admit, the world of cutting-edge fashion can all get pretty confusing after a while and almost impossible to keep up with. With hundreds of trends flitting in and out (and then back in again), what’s a girl to do?

If you’re looking for something more permanent than the latest must-have accessory, here are four styles that never look passé.

1. Preppy

From Faye Dunaway in Bonnie and Clyde to the ever-stylish Jackie O, the preppy look of private Ivy Leagues and summers on the Cape has always been cool, chic and classic.

The preppy essentials are pretty synonymous with classic. After all, what girl’s closet would be complete without her cardigans, little black dress, and ballet flats? Today’s preppy is done in luxe materials with a fashionista spin, but just ask those New-Englanders and they’ll tell you “If it ain’t broke, don’t fix it.”


Jackie O. (1960s) and Fay Dunaway in Bonnie and Clyde (1967)


Preppy style
Leighton Meester in Gossip Girl and Reese Witherspoon in Washington DC

2. Rock and Roll

Sandy from Grease and Madonna in Desperately Seeking Susan epitomized the rocker-fabulous look of the 80’s. While the leather motorcycle jacket has been heralded as the next big thing for several seasons now, it’s never really been out for those edgy fashionistas.

A slick of red lipstick, tight jeans or a black jumpsuit, and that perfectly worn-in leather jacket make an instant femme fatale statement, no matter the decade. After all, when has a little rebelliousness NOT been in style?


Rock and Roll style
Madonna in Desperately Seeking Susan (1985) and Olivia Newton-John in Grease (1978)


Modern Rock and Roll style
Agyness Deyn and Marie Claire 2009 “It Takes Two” editorial

3. Menswear/Androgynous

Is there anything sexier than a woman wearing a man’s clothing? I’d say not.

Coco Chanel knew that when she introduced the sporty, “little boy” look to women during the 1920s. Marlene Dietrich and Diane Keaton knew that back in the 1930s and 1970s. Rihanna and Diane Kruger know the same still holds true today: masculinity of guy’s clothes seems to accentuate the fact that, yes, you are a woman.

So while the boyfriend blazer, jeans, cardigan, etc. are deemed “trendy” right now, they are really more classic than anything else.


Menswear inspired style
(Marlene Dietrich (1930s) and Diane Keaton in Annie Hall (1977)


Modern menswear style
(Diane Kruger in Vogue Germany 2010 “Dandy Diane” editorial and Rihanna)

4. Boho

Boho-chic is a style with roots alluding to peace, women’s liberation, and a whole lot of free love. While Yoko Ono was more on the minimalist side for a boho woman, 1970s Cher with her long hair, deep eyes and careless (dare I say?) tribal style is an example of a more high-maintenance laid-back beauty.

The Olsen twins are the modern queens of the boho-chic look, just check out their effortless “I just rolled out of bed and threw this on” style, complete with rumpled bed-head and smudgy liner from last night. For a casual, comfortable and chill style, nothing beats the beauty of boho.


Bohemian style
Yoko Ono and John Lennon (late 1960s-1970s) and Cher (late 1960s)


Modern boho style
Flora by Gucci advertisement and Ashley Olsen

What do you think?

Are there any other styles that you consider timeless? Do you like any of these styles? Which one is your favorite? Let us know in the comments!

Posted on on April 10, 2010 / Filed Under: Fashion Tips / Tags: , , , , , , , , , ,

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25 Responses to “Four Timeless Styles That Will Never Go Out of Fashion”

  1. 1
    April 10th, 2010 at 1:19 pm

    Great feature! The preppy style is my favorite. (I’m from Boston, what can I say?)

  2. 2
    April 10th, 2010 at 1:54 pm

    I definitely have to agree with the menswear on women theory– it has to be my favorite! But I also like to experiment in all the other styles, it keeps the wardrobe interesting. :)

    Love this post!

  3. 3
    April 10th, 2010 at 1:56 pm

    I love this post! I actually try to keep one of these four themes in mind when putting together an outfit, haha. (Well, not menswear very often actually, it’s just not my thing) So true, these styles will never go away.

  4. 4
    April 10th, 2010 at 2:22 pm

    Great post! I totally agree! And the preppy style is my personal favorite! One of the reasons I LOVE Gossip Girl is the great fashion!

  5. 5
    April 10th, 2010 at 2:43 pm

    i love preppy style and Jackie O is a personal style referance for me! although at the same time, i do love a good boho look as well….

  6. 6
    April 10th, 2010 at 2:46 pm

    I love the preppy style. I don’t have much clothes so i’m planning to buy plenty of clothes, the preppy style is definitely inspirational for that. Thank you for the article. College fashion and the new writers rock !

  7. 7
    April 10th, 2010 at 3:01 pm

    Although, as a New Englander, we never say “ain’t” but rather would say “isn’t.” (I only say this from having moved to the south and having pride my own regional dialect)

  8. 8
    April 10th, 2010 at 3:22 pm

    I just love the preppy and the rock & roll but I really dont like Boho at all, meanswear I dont mind a piece here or there but ALL menswear I think only flatters those that are really slim.

  9. 9
    April 10th, 2010 at 4:45 pm

    Hannah- I’ve lived in Boston too for a while before moving to NYC, and as soon as I see preppy or anything related to the Kennedy’s, that’s the city I think of.
    While Bostonians aren’t particularly fashion forward, they definitely know how to spin a classic and preppy look.

  10. 10
    April 10th, 2010 at 4:50 pm

    Carolanne – I agree! I watch Gossip Girl for the fashion too! Preppy always looks put together, and I love it.

  11. 11
    April 10th, 2010 at 9:17 pm

    *sigh* Blair/Leighton, one of my inspirations.

    in order for me it’s
    1) Rocker (heck yeah!)
    2) Preppy (so cleeeean)
    3) Boho (so flowy and my friend’s favorite)

    I’ve never tried the androgynous look though.

  12. 12
    April 10th, 2010 at 10:00 pm

    You should have put Leah Michelle as Rachel in the preppy place. She’s such and inspiration for that style!
    The style I use the most is the Rocker… then would be Boho and then Preppy, although I don’t use it that much. It’s clean, but for my body type and my skin color it looks… wrong :P

  13. 13
    April 11th, 2010 at 2:10 am

    I agree with this post. I do keep these 4 styles in mind. But when I’m choosing an outfit, sometimes I fuse 1 or 2 elements from 1 or 2 styles… just to shake things up a bit. I dunno. I like things to be as unexpected and spontaneous as possible.

  14. 14
    April 11th, 2010 at 5:02 am

    I loved this post and I totally agree, these styles never go out of fashion and new things actually develop on these.
    I use 4 of them in my outfits but the one I love the most is to add rocker edge to preepy clothes!

  15. 15
    April 11th, 2010 at 10:32 am

    oooh i really, really love this!! so inspiring!!
    you’re so right with the constant changing on fashion we don’t always know where we’re up to, but this was fab :]]]
    i’d love to see more of this kind of post!!
    maybe you could do a few outfits for each section? that would be awesome!! especially with all the boho dresses and denim in, preppy sportswear, blazers and leather at the moment, you could help to do a modern interpretation on all the above styles?



  16. 16
    April 11th, 2010 at 11:51 am

    great post
    i love the androgyonus and rocker chic look
    also think preppy is cute

  17. 17
    April 11th, 2010 at 3:21 pm

    This is very clever inspiration. I like seeing the juxtaposition of the trends then and now.

  18. 18
    April 12th, 2010 at 12:29 am

    Annie Hall is my fashion inspiration (Ijust got the DVD for my birthday this past week!). One of my teachers in high school once told me I dressed like Annie Hall and then he said “if you even know who that is”. It was the best complement I had ever gotten :)

  19. 19
    April 26th, 2010 at 3:07 pm

    That is Mary-Kate pictured, not Ashley.

  20. 20
    October 16th, 2010 at 7:27 pm

    My favorite is the boho style since I dress like that most of the time.

  21. 21
    June 12th, 2011 at 6:08 pm

    I love mixing rock n roll clothes with bohemian clothing which is so me and I love the whole inner peace within myself and loving the environment for the 60’s inspired clothing. For an edgy vibe, I would pair a leather jacket over a white blouse.

  22. 22
    August 6th, 2013 at 5:18 am

    Nice! I agree with the styles listed. I’d describe my style as conservative/preppy; love it. :)

  23. 23
    February 15th, 2015 at 5:45 am

    Great article! You forgot the femme fatale though. Those six about sum it up.

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