It is hip to own almost nothing. Beyond having what you need, excess is gaudy. I admire the people I know who own surprisingly little, because they are great at editing. The search for the perfect thing is ongoing and delightfully tedious. A picky shopper is a hip shopper.
Aspire to own the bare minimum of the most basic possible garments. Fit is everything, and it's more about what you don't wear than what you choose to wear. Avoid all embellishments and focus on cut and shape. Only then can you actually start to break things in. Wear things out! Worn clothing is not only hip but also sexy. If it was good to begin with, it gets better. Why not own only 2 t-shirts? Let your jeans rub holes in them. Let yourself rub holes in your jeans.
Most clothing is a giant visual distraction. I want to see people. I want to see faces. I want to see women in a plain black or white t-shirt and jeans. At some point, we have the option to dress like sophisticated grown-ups. We have the option to stop wearing GI Joe baby T's from the kids section at K-Mart paired with camo pants. If the mood strikes us, instead of being inspired by early Gwen Stephani, we can dress like La Femme Nikita in her little black dress, but still tough and "quirky". If you need further personality, slather on some very berry lip gloss and toss your hair up in a scrunchy. An extra t-shirt takes up too much space in my life. I want my wardrobe to fit in a duffle bag. (Shoes are a different story.)
Doesn't matter what style you have, but have one. One. If your thing is "playful summer prints," god bless you. You are probably a bubbly person. If you are that person, then have a few great summer dresses in flattering shapes and colors, and wear them to death. Accessorize, and make them a part of you. Wring out every bit of life you can out of them. You'll be tired of them next summer anyway, and it'll keep you from having piles of color littering your room.
Creativity in dress is refreshing, but it's easier to achieve when you have less to choose from. Traveling is the best example, because we all survive with less on the road. When you have a uniform of perfectly fitting basic garments, then just mix and match. Accessories play more of a starring role then, so don't limit yourself on shoes. They transform everything! Jeans and a t-shirt with flip flops vs. jeans and a t-shirt and black stilettos are entirely different women. This is my morning opinion as I look lovingly at a shelf of my little babies.
I think about this when I see attractive people detracting from the view by wearing a mess of nonsense. It is only clothing. Life sure is easier when you have less though.
*all photos are either from Vogue Paris, the Sartorialist, Garance Dore, or style.com