Does Tom from 500 days of summer dress well?

I've been saving up some money to go clothe shopping, and I found a lot of places to dress similar to him. Like a sweater vests, some dress up shirts, and cardigans. Do you think it would be too weird to dress like that for school and outings? I'm also getting just some plain tee's and stuff. But I really like the way he dresses, but I would like peoples opinions on it. Thanks.