Shopping613- that’s part of the difficulty of peer pressure; many of us want to do things differently than the crowd, but we feel stifled by others’ judgment. Some people react with reverse judgment- basically judging their judgers- but I don’t think that’s right, either.
The best way is to work on being confident and comfortable with who you are, and to try not to care so much what other people think. It’s extremely difficult, but it’s doable.
I personally do not buy a whole new wardrobe every season. I buy to fill in the gaps of what is unusable from last season, or the season before that, or 5-10 seasons before. Sometimes that could mean buying nothing new, if my clothing remained intact. My main objective is that my clothing looks nice on me and I feel good in it. It doesn’t have to be at the height of fashion.