A girlish beret from Urban Outfitters.

I dropped my favorite winter hat (a knitted beret-type thing) in my sister-in-law’s parents’ driveway on Christmas, so until my s-i-l gets around to sending it to me, I’m stuck with the second-tier hats in my collection–a floppier, flimsier knit beret, a classic wool beret, and a giant faux-fur concoction that makes me feel like an extra in Dr. Zhivago. (This is actually the second time I have lost my favorite chapeau–I bought another one after I lost the original within a few weeks of its purchase. As you can see I get attached to my hats.)

It drives me crazy when I see people on the street who have obviously given no thought to how their winter outerwear–coat, hat, scarf–looks together. Colors have no relation to each other, textures are at odds, styles are all over the place. Not that everything has to be all matchy-matchy, but there should be some harmony amongst the elements.

Cashmere cloche by Eugenia Kim.

Outerwear is a part of an outfit–in winter especially, a lot of people you pass on the street are never going to see your cute dress or your new sweater. All they’ll see is your coat, your hat, and your scarf. Hats are a very noticeable accessory, so it’s worth it to give them some thought and make a little investment. Whether you go for an ironic pom-pon hat or an elegant wool cloche, make sure it works with both your outerwear as well as how you’re feeling that day–playful, glamorous, or retro. That’s why it’s good to have several options ready in your closet. And with the holiday sales on now, you should have no problem picking up a few on the cheap.