Dear Rosie, that reflects your own fashion past, and good on you. Others may be cringing for other reasons, chief among them Why did I wear what my mum/my best friends/my gang/a fashion magazine said I should, though it made me feel crap? Or Why did I wear those drab cords for years and years, afraid to wear something bright that might risk making someone notice I was there? Shame and regret come in many flavours.