/fa/ - Fashion

Trying to decide between these 3. Leaning towards the last one because it's cheaper and would look acceptable in most situations. Is #2 too flashy/old timer looking? Could I wear it on a night out in say either tshirt or button up and jeans? I work in software so definitely not there. I like 2 and could afford it, but it's maybe too much until I can get the rest of the lifestyle to go along with it.

>25
>tall skelle mode
>wear a button up to go out, even work though I don't have to
>work in software
>live with parents and drive a camry - cashed out biz gains with the explicit intention of buying something nice and a little show offy. I'm otherwise a cheap bastard