i'm basically hybriding czolgosz and omystarling's answers, especially as – fun fact! – i'm actually undergoing something of a wardrobe morph as well. it's kind of like a hybrid between "oh i live in a new climate" meets "oh i'm no longer in an office environment" and a bit of "huh, my new lifestyle means i might be losing a pant size soon" with "frick, where did my painting clothes go??"
but yeah, when i first developed my ~style~, i had lost a reasonably ridiculous amount of weight in ways that i would not condone for your health but happened nevertheless. so it was literally utility: oh crap, my pants are sliding off my body, i better think about clothes. around this time, i was also entering herron for the first time, so it was like "omg i can dress myself like an art student!!" so a lot of developing how i wanted to look came with looking to fellow students i admired and the look they were cultivating. around that time, i was also looking to a lot of fashion blogs + websites i wanted to dress from + just thinking about how i wanted clothing to interact with my image in general. (man, art school makes you think about this a LOT, gosh...) so that's how my initial emergence into style happened. lots of shorts + tights and dresses with docs were featured. hell, the dress + boots equation is still something i do on the reg.
my second evolution in style came when i was working! flannel and jeans does not a proper office individual make, so i had to buy a lot of inexpensive staples fast. blouses and cigarette pants became a uniform i deviated to, and jcrew became my bro. who knew i was a tiny prep waiting to burst free?? granted, i was also entering my late 20s, which i think helped a lot. i still have a lot of punk feelings inside, but i wanted to look good and that usually ended up with this sweater-and-blouse look that i gravitated to a lot. it also made sense, as it happened.
now that i'm back in the studio but in a graduate experience, i'm trying to balance the things that i liked from my office couture and what i liked from earlier without looking dated. a lot of clothing is as much about utility as it is expression, which is why i think that cairo's comment is so important. similarly, chels's mentioning of smart staples that can last you for ages is similarly out of the ballpark. when i buy things, it's generally with the knowledge that i'll have to live in them a long time. i don't have a budget to buy a lot of clothes, so keeping around a few staples (a grey skirt that looks good AND professional, blazers, etc.) are super-important.
another thing: if you have certain things that make your body special/different and clothes affect that, keep that in mind too. i have flat feet and a shortened achilles' tendon, so buying good shoes that ensure that i can stand for hours at a time in the studio is IMPORTANT. it's why i paint in docs: not JUST because of the cool factor, but they keep my back healthy and my endurance going for hours in the studio. similarly, when i was at work and had to be working events for hours in heels, making sure to spend a little more to get a pair of clarks' heels was important because hell hath no fury like the feet of a woman in bad heels for fourteen hours straight. take care of dem bones, y'all!!