I must be frank - I've been playing a lot less dress-up.
Not because I'm not actually dressing up. (I make a point to do that. Every day.) It's because there's a lot less guesswork in reaching for my wardrobe in the morning these days. My style has crystalized into something that I hope communicates my essence, wordlessly, in just a glance. It's a style that I want to project a statement about who I am without distracting from what's going on inside. (I've also been wearing a lot less heels.)
Translate to: function, fit, and flair, in that order.
I've got a booty and strong shoulders, so my aim is always to emphasize the hourglass. I reach for straight legged pants that sit above my hips (mostly these from Levi's), or high waisted skirts that hit at the smallest point of my waist, just below the ribs. Worn with button-ups and sweaters borrowed from the boys, or something strappy or cropped to show off the girls, I always top the look off with a great jacket (and a scarf, duh) to define my shoulders.
Versions of these pieces in clear reds, denim blues, sandy brown animal prints, or stripes and polka dots in black, white, gray, and navy make it easy to mix and match. (Though I'm always willing to throw in some turquoise, or cobalt, or hot pink...)
It also makes shopping easy - I look for updates that work with my preexisting MVP items, things that play nicely with what I already own. The red pleated skirt I just scored at Francesca's Collections will pair seamlessly with all the American Apparel cropped tanks I bought last summer. Same with the new Chuck Taylors that already get along swimmingly with my skinny jeans, since they hit at the same spot on my leg as all my ankle boots. It's about identifying the silhouettes and fits that make you feel your best and then playing within those parameters.
Then it's time to add the spice. How about some sparkle with gold hoops? Some smoke with a flick of eggplant-colored eyeliner? Maybe a choker that your friend bought you from a dominatrix shop or a woven clutch you accidentally stole from a street vendor in Rome?
Accessories are the easy part, the basics are anything but.