Thought provoking. After joining YLF I did finally totally put down the Prep and am much happier sartorially for it. It wasn’t the criticism that worried me; I learned long ago chutzpah pretty much makes everything work. I guess it’s that my life is steeped in preppiness in every other way and I didn’t know if it would work...

Interesting reading, Carla and many commenters.

As for myself, I actually don't feel I have taken any sartorial risks. I usually don't see view wardrobe items as risky, unless they are worn in a completely strange setting, like sporting a swimsuit as office wear or wearing stilettos in deep snow, which I have never felt the slightest temptation to do.

But I do know that up through the years, others have viewed some of my choices as rather courageous--like insisting on going grey when "all others" indulged in dying, or wearing midis when few others did so, or sporting bold, colourful glasses that noone around me dared to wear.

If you feel comfortable with your style, if it's a natural reflection of your personality, and if you wear it with confidence, people will often respect you for it and enjoy it. That's my general experience. And it feels kind of liberating to have a personal style instead of dressing like anybody else.

By the way, thank you, Carla, for the inspiration to continue to evolve our personal styles and try new things!

The past couple of years, wide floral trousers, ankle length trousers, loafer sneakers, Birkenstock style sandals, a long pastel blazer and a long slim sleeveless pleather tunic have been among my successful new-to-me-items.

Risks are relative, as you say!
Never had booties before YLF.
Also had poison eye for cropped pants , but now totally “ need” them ( in some seasons) for my style.