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Ask Painfully Hip: Spring Tips for a Tomboy

Hi Amber,

My clothes were stolen from the dryer today when I was doing my laundry. It was almost everything I own and almost all of my good things that I wore out to lunches and dinners over the weekend. I have to go shopping this weekend to replace my dresses and jeans and sweaters, since it is still quite cold in England.

Do you have any tips for a tomboyish girl this spring?

Thanks, Morgyn

That is some tough luck. Petty thieves should be strung up by their sticky fingers. I’d be happy to help out a laddish lady in need, even if soon after this letter was written her lost wardrobe was recovered. PHEW! I’ll answer it anyway with my favorite boy-inspired looks for spring. Most of the time I like to dress girly but I notice that tomboyishness is my tendency when I really want to be comfy. Here are my top hip tips (click photos for sources).

cigarette jeansbw

Cigarette pants and jeans. Alter some old broken in thrift store jeans (colored or acid washed denim is what i’ve been looking for) into sexy tapered cigarette pants and capris (maybe roll them up a little) to wear with boyishly nonchalant oversized plaid shirts, comfy v-neck tees, crisp white button-downs, blazers, vintage floral tunics, chuck taylors, chunky boots or sandals.

turquoise blazer fashion toastgray cardiyellow cardi

Shrunken blazers and oversized cardigans. For chilly evenings and breezy days play with proportions and get thee to the boys’/petites section of your thrift store for tiny fitted blazers. The trick is to make sure they fit real good in the shoulders or they’ll look dumpy/butch. Then find an oversized cardigan with slightly fitted sleeves. Wear either with the sleeves scrunched up over girly dresses, tanks, and band tees with high-waisted short shorts, mini skirts or cigarette pants.

sherbet tonefacehunter

Masculine hats and accessories. I know it’s tempting to soak up as many precious rays as possible at the beginning of spring. (Believe. I’m a sun-worshipping California native who lived in the pacific northwest for 7 years!) but make sure you protect your youthful non-cancerous skin from the sun, everyone’s secret adulterous lover. Wear an old man hat, newsboy cap, fedora, or bowler (Brat Pack style) with practically everything. Seriously, it’s bitchin’ time: sunscreen disintegrates into nothing, even after only a couple hours and you know you’ll forget to reapply. Just wear a hat. Some grampa suspenders, fitted vest or a stripey tie couldn’t hurt either and are always good for a dash of schoolboy charm.

Thanks, Morgyn!

Hey hipsters, keep the questions comin!

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Lucky Brand Jeans

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12 Comments so far (Add 1 more)

  1. that facehunter girl is spectacular.

    1. Prêt-à-Porter P on April 7th, 2008 at 7:58 pm
  2. The black and white jacket in the first pic is gorgeous and I’ve been looking for one exactly like that for ages… now I want one even more!

    2. Amy on April 7th, 2008 at 1:06 pm
  3. I love the 4th image, the one with the blazer, the shorts and the boots. Such a good look. Gotta love them gold buttons!

    3. Cellar Door on April 7th, 2008 at 10:38 am
  4. That poor, poor girl! I’m terrified of doing my laundry now…

    4. The Clothes Horse on April 6th, 2008 at 8:07 pm
  5. definitely not cool, this happened to me a while back. Shame on those who laundry steal. But on a happy note I do enjoy fedoras and vintage jackets. I do ties or slacks when i dont feel to girly.

    5. Stephanie on April 6th, 2008 at 4:41 pm
  6. Wow, what an awful thing to have happened. I go to a drycleaner and sometimes I swear they lose my socks, but I have never had my stuff stolen :( I agree with Kelsie, this was a very fascinating and great original post

    6. Rachel on April 6th, 2008 at 1:26 am
  7. omg I would have died if this happened to me!! AAaah! My clothes! But anyways, I’ll need a truck to take all my clothes to the laundry..

    7. Alya on April 5th, 2008 at 11:32 pm
  8. I feel so bad for this girl, people are rude!

    8. Hailey on April 5th, 2008 at 9:20 am
  9. All excellent suggestions… off to the thriftstore!

    9. Missa on April 5th, 2008 at 7:18 am
  10. I dont know if this is how youre supposed to ask a question. But, my question is, since its already reaching 90’s in Florida, its already shorts weather. I need help on how to wear shorts, without looking like someone from Abercrombie and Fitch. Thanks.
    ——Shae

    10. shae on April 5th, 2008 at 5:32 am
  11. this post was great, thanks!

    11. kelsie on April 5th, 2008 at 5:09 am
  12. Gotta love the preppy blazers, and well, hats if I they suited me (even my own Mum gave up on them after realising how ugly it made me look as a baby/toddler!)
    I do like ties on women too, if anyone wanted to know..

    12. Baraginie on April 5th, 2008 at 4:58 am

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