Leveling up in the Fashionista Skill can seem to be really confusing. The best way to level up is to do the every day things that you do, in addition to the following: change clothes often. Changing clothes helps improve the skill. The skill is also based on how many clothing items you own. So if you own a lot of items, but dont move much, try trading clothes with people and trying on many different items. Trying things from auctions also helps. Attending a Fashion event also helps level up faster.