Photos: The Social Shopper: October 29, 2011

While many women, myself included, usually prefer their makeup to at least appear au naturel, there is a new brasher, bolder, and highly experimental movement afoot: matching your lipstick (or hair, nails, mascara, whatever) to your look. While this explains a recent rash of double-take–worthy orange lips, pink—or pink-tipped—hair (hello, Thakoon spring 2012!), and wild, mosaic nails, if it’s done wrong, you could end up seeming a little too Happy Halloween. Even when taking a risk and trying something new, which we all applaud, no girl wants to end up looking like a clown. That’s why we love this picture of Caroline Sieber on stockholm-streetstyle.com. First of all, she opts for bright red from head to toe. Then she takes the idea of monochromatic dressing to a whole new level by topping off the look with a near-identical rich crimson lip. The effect cannot be overstated. And, sorry, P. T. Barnum—you’re going to have to seek elsewhere.

Knowing it’s not easy to pull off, we dedicated this week’s shopping list to the pursuit of color matchmaking. Here are our picks for you to test-drive this weekend. Don’t forget to keep it social. Send your own ideas and favorite products to us via Facebook, commenting on Vogue.com, and Twitter. We will update our list (and give you the credit) early next week.