why don't you rebuild your wardrobe with some simple basics first?
how many tees do you need? in what colors?
how many knits do you need (sweaters (crew/vneck/t-neck), cardigans etc.)? what colors?
what type of shirts do you need? colors?
stick with the basics then once you have covered the essentials, save and blow your money on the grails.
as someone mentioned, why would you spend your money on outerwear (TOJ) or baller shoes when you do not even have a nice shirt/sweater to wear/layer underneath? get the idea?
the other way of thinking about it as what the intention of this thread was, is to look at an aesthetic that you think will fit your personal style/character and then mix it up with grail and cheap basics, AND still end up looking great. i think the latter is more sf approved, but i have chosen personally to go with the former. the latter idea allows you to buy a few simple basics, then mesh it with great designer pieces, and based on your experience and knowledge, you should be able to put together a concurrent outfit that flows rather than looks choppy.
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of the two, you also have to think about what your scenario is like?
i think the latter is a better idea for say a college student because it really limits IMO the amount of outfits you can put together. i mention college student though because honestly, it's college and you should be worried less about how many outfits you can rotate in a week. find one solid outfit that you can change up 1-3x and just put it on repeat. should be constant swag sauce you know?
on the flip side, if you have a job, the opposite idea applies. unless you work for yourself or for a really 'lax company, i highly doubt wearing the same thing everyday is approved. but hey, this is sf, who needs peer approval when you got approval from the internet