A ridiculously long time ago, I had the following lovely email from Kristen:

I’m 30 years old with 4 yo boy/girl twins. I stayed home with them until they started preschool in August of last year. Now I have a flexible job where I work the same hours that they’re in school. My job is really casual i.e. jeans and sweaters are just fine. When I wore slacks, white blouse and a sweater vest one day, my boss wanted to know if I had an interview somewhere! I’m at a community development not-for-profit organization so I generally work/meet with people in similar offices and dress codes. Personally, I would prefer to spruce up a little more, but am met with comments *all day long* when I do so I just tone it down: dark jeans, button-down, thin knit sweater and a pretty necklace.

I recently bought a lovely pair of dark olive green driving mocs. They have a bit of sheen to them although I wouldn’t exactly say they’re patent. They have the treads on the bottom which lends a more casual feel. When I bought them, I envisioned wearing them with everything: khakis, jeans, etc. My problem? SOCKS! Color? Texture? I’m really sad because I haven’t worn my shoes at all yet. Trouser socks seem too insubstantial and slippery, but I don’t know about cotton crew socks. Both brown and black socks just look wrong to me with the beautiful green color.

Kristen, I hope those shoes haven’t been sitting the closet all this time, because they sound fantastic.

For very very casual offices, like Kristen’s, great shoes can be an easy way to dress up your look without your coworkers wondering where your interview is. A pair of really cool colored shoes can change your whole look without starting any office gossip about how you are job hunting.

Kingston suede driving mocs in fresh pine, J. Crew, $128.00

Colored shoes can be tricky, for precisely the reason Kristen has articulated here: what do you wear WITH them? I will confess that I only rarely wear socks (today, in fact, in a total coincidence, I am wearing MY green driving mocs with toe socks because it is cold and having my toes covered is as far as I am willing to go). But if you live where it is cold, or you just don’t like the look of bare ankles in the winter, you have a couple of options.

Match your socks to your trousers. Brown socks with brown pants, black with black, navy with navy. Go with navy socks with jeans, because OF COURSE you are wearing dark wash jeans, which are VIRTUALLY navy blue themselves.

I have to pause here and say that I do not love this solution. At all. I think that a BETTER solution is to wear boots on days that it is so cold that you MUST cover your feet, or wear a skirt in a dark neutral and match your tights to the skirt. The tights-and-skirt look is great with colored shoes because it is unexpected, for starters, and because matching tights and skirt creates a long leg line. This look is better, though, with pointy toed shoes, because they keep the line going, even in a dramatic color.

Weather permitting (which for me means that it’s not snowing) Kristen can wear her driving mocs with pretty much anything. Driving mocs are perfect with capris and longer trousers, with skirts and Bermuda shorts, or with very simple dresses (like a sheath dress). They can be paired with chinos for a stylish casual weekend outfit, or with wool trousers for an office look that isn’t too dressy. Even in colder climates, pairing long wool trousers with bare legs and driving mocs shouldn’t be uncomfortable.

Driving mocs are also the perfect summer shoe (if it’s too cold where Kristen lives to even THINK about going sockless right now). She can wear them with jeans and khakis and shorts and with a denim skirt or a sundress or …

The options are endless. Truly.

Your turn: what do you wear on your feet in the winter? I can’t be the only one skipping socks, can I?

Subscribe to blog via RSS