During middle school and some of high school, I didn't like clothes. At my worst, I would wear the same three or four shirts all the time and the same jean jacket all winter. But then I questioned why I purposely held myself away from the world of clothes; I started dressing a little better and actually doing my hair (although, ironically, I often don't do anything to my hair now--its half-curliness fits in well with certain hair trends). And now I like clothes.
I like them as an extension of myself, so I like them to reflect things I care about. I love Arizona, so even if Southwest isn't my general style, why not throw in a pair of moccasins sometimes? Or silver heart earrings with a little turquoise? A basic garnet ring from Sedona and a Native American beaded necklace are two other Southwest items I own.
Nineteenth-century is my favorite literary era (overall) and my decorating style is also Victorian-ish. So I love my outfits to have lace, vintage floral patterns, skirts, cameos or other antique/vintage jewelry, and whatever small amount of layering an Arizonan is able to do (not much in summer, but late fall and early spring can be perfect for layering).
When I wear my black Guess dress, which has a sixties-inspired skirt shape and exposed zippers that give it a modern touch, I often like to pair my cameo with it to add contrast. Alternately, with black-and-white checked dress I might put a vintage silver-colored, twisty-patterned necklace that adds a little edge to the outfit.
You see where all this is going? I didn't like clothes before because I thought of them as clothes, as established things that were an entity of themselves and would define and categorize you. But I like them now because I choose them and put them together as I want to. I try to dance around trends and never really put together an outfit exactly as someone else would. It's the creativity of the process and where I'm drawing my inspiration that I love. That's why I love vintage jewelry a thousand times more than new jewelry: it has already lasted through at least a few decades, so it won't go out of vogue in two years and it's more likely not to be cheap material than something you buy at Buckle or wherever. And you probably won't bump into someone who has a piece like it.
While I am on this subject, let me guide you on to a YouTube channel I have been enjoying: whisperingsandstars. (Notice that the channel name comes from a Great Gatsby quote.) Robyn Schneider is author of four books, with two more on the way, (her sometimes pseudonym is Violet Haberdasher), and many of the clothing pieces she uses are vintage. More than wanting to copy her exact outfits, her videos lead me on to think of clothes in my strange, half-vintage-style way. Clothes don't have to define you, but if you like, you can define your clothes.