Mail Bag: Socks with Dressy Flats

Hey there, I have to say I love your blog. I'm not sure if you have time to read emails from random people like myself, but I have a winter shoe question. I'm a teacher and I wear pants to work everyday (I buy short, not regular, because we aren't really allowed to wear heels if we have to run for some reason)...SO, my question is how to pull off a flat in the winter. Is it really bad if your socks show? Should the color of the sock match the color of the shoe? OR... Should I just invest in a ton of knee highs? But then I'm worried my feet will freeze!!

IF you have time I'd love to hear your advice, or maybe you could do some shoe advice posts. Anyway I understand if you're too busy to respond, but keep up the good work!!

Erin

Dressy shoes, whether flats or heels, can be difficult to pair with socks. There is little wiggle room, so your socks must be thin. The shoes usually have a low-cut vamp, so your socks are on display as well.

If you are wearing a skirt, the simple winterizing solution is a pair of tights. With pants, though, you’d probably prefer a sock that ends at the knee or below. The best option is a hosiery-like sock. Also known as “trouser” socks, these can vary in thickness and opacity, but none are truly warm.

The color depends on your personal style. You can wear nude fishnets or opaques for a bare look. Match the sock color to that of your shoe or pants for a more streamlined look or wear a sock in a contrasting color for some "pop!" I have a pair of leopard print trouser socks from Sock Dreams that I often wear with my tap shoes. I bought a pair of nude trouser socks printed with tattoo designs that are a lot of fun, too.

Simply put, the type of socks you must wear with dress flats might be cute, but they won’t keep your feet warm. Why not consider some other options?

To keep my feet toasty outdoors in the winter, I wear rubber galoshes paired with thick socks. Once inside, I take off the galoshes and socks and pull on trouser socks and my impractical shoes. If you go outside for recess or to supervise outdoor activities, you might consider keeping “outside” shoes at work. You could use my galoshes/socks trick or even *gasp* some Ugg-like footwear.

However, if I were in your situation, I'd wear a flat boot for work during the inclement months. You can wear thicker socks (if you size the boot appropriately), the boot itself will help keep your feet warm, and the color of your socks doesn’t matter! I’m not sure of your work style, but Minnetonka makes a number of flat, warm-looking boots and booties. Cowboy boots are also a nice option. They are generally waterproof and loose enough that you can wear regular socks inside of them.

I have a sit-down, ass-flattening job, so I’m a little out of my depth when recommending stylish footwear options for those on their feet all day. Any advise from my readers, teachers or otherwise? Has anyone found a thin, stylish, and warm sock to wear with dressy flats?