The most memorable fashion moments in history were never made by playing it safe. Treading the line between faux pas and forward-thinking is the key to developing a fearless sense of personal style. In celebration of _Vogue’_s August Age Issue, we’ve put together a bucket list of fashion risks to have tried by your 30th birthday.
You should have . . .
1. Stepped out in thigh-high boots and a miniskirt at least once.
2. Adapted something from a school girl’s uniform-pleated skirt, Peter Pan collar, or over-the-knee socks for your working wardrobe.
3. Exposed a cowboy boot.
4. Taken to the streets in a nightgown.
5. Done sequin pants for day.
6. Gone goth, punk, or grunge for the night.
7. Reinvented an oversize men’s blazer as a dress.
8. Blown your tax return on a pair of skinny leather pants and regretted it.
9. Worn a “signature” hat.
10. Referenced at least two of the following for inspiration: Joan Jett, Jane Birkin, Bianca Jagger, Stevie Nicks, Kurt Cobain, or Anita Pallenberg.