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At school I've sort of got into the usual and lazy trend of jeans and a tee. And sometimes a sweater. It's been going on for like years already, and if I suddenly switch to wearing something different like a skirt, people might start saying that I'm trying to get attention or what I'm trying to impress a certain someone. Any ideas about what I should do?
I have no fashion sense, but in response to your other question (apart from who cares what they say) try doing it slowly, so wear a cute shirt with jeans. Some people look good in capris? Maybe boots? The idea is to change things one at a time so that it isn't obvious. Eventually when people are used to seeing you dressed up, then comes a subtle skirt, then a pretty one...
Or you could pick one day a week to dress up, even better convince a friend to join you, and just say you want to have pretty ___ day...
You could try wearing a skirt with tights or leggings to kinda break into wearing a skirt gentally. Go for bright colours if you wear jeans and tees add acessiors as well, they always help to carry the outfit.