Friday, November 13, 2009

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!!


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?


Grace said...

This is my problem as well. I am a cold person and a teacher as well and wear three pairs of socks at home and even in bed. I wear low heel oxfords for the winter and wear some argyle pattern socks because their coloful combinations usually match my shoe at least one of the colors and even though I cannot match th ecolors perfectly they look smarte than the other options to me(to me only?) I found thid picture and most of them do not look bad. Any better ideas?

Grace said...

Sorry about misspellings. I also missed this link. I like these combinations and think they eill work good in winter for the cold- trousers-wearing person.

Rosie Unknown said...

I'm not on my feet all day, but I definitely agree with the boots idea. If you wear boots, I recommend Smart Wool Socks. They are a bit more expensive, they are really warm, and I swear, the W's PhD Outdoor Styles ( offer amazing foot support. I have no idea how it works, but when I wear these socks, my feet don't get sore, but in the same shoes with other socks, my feet hurt.

Anonymous said...

I am also a teacher. We are allowed to wear heels though and I often do. I have found that boots are a great option. I started wearing ankle boots with pants about 5 years ago and found this to be one of the warmest solutions. I would wear average thickness of socks with the boots and be toasty. Depending how cold you are, sweater tights are also an option as long as the pants aren't too tight. I know, tights under pants... but this really works to keep you warm and the sweater tights can usually be worn with loafers or other slightly casual flats without too many issues. I have noticed a lot more variety in knee socks in the stores this season too. Target had some dressier normal thickness knee socks that could be worn with dress pants and flats.

Personally though, I often do as Kasmira and where my socks and snow boots or rain boots outside and switch to the dressier shoes inside with less warm tights or socks. I find that our building keeps me pretty warm if I come into it being warm in the first place.

Christy said...

I love Hue Jeans Socks. They're thin enough to wear with my flats yet warm. (My flats have a slight give to them, though--not skin-tight.) There's no tight elastic band yet they don't fall down. They come in pretty basic colors--I usually wear my gray or black ones with my black flats and my dark brown or light brown ones with my brown flats. Kinda predictable, but I don't care. They do have a couple of striped ones that offer a bit of punch.

Raquelita said...

I'm a college teacher/PhD student, and I also really recommend going the boot route. This is particularly good for inclement weather that way you don't get snow, slush, and cold water on your socks/tights and feet.

Heidi said...

I'm starting to knit my own socks to wear with my cropped dress pants and oxford shoes.

ebinbaby said...

As someone who lives north of Fargo (yes there is still civilization way up there!) I am a pro on cold feet and socks. I always wear winter boots to and from work and carry my inside shoes to work. I also have summer and winter shoes due to the extreme weather so I have some shoes I wear with socks and some without.
As my feet are often cold inside work I sometimes use a combo of super thin cotton socks under thin wool socks to keep them extra toasty. If wool doesn't make you itchy then I'd recommend straight wool socks as they are warm even in a very fine weight.
I'm not sure if it's good blog etiquitte to do this but I'd recommend checking out for comfot shoe suggestions. I adore Kasmira's style but could never pull off the heels so I rely on Kirsten to help me find funky comfortable shoes!

Christina said...

My feet get cold super quickly, and I'm allergic to wool, so I tend to stick to black or skin toned cotton blend socks during the winter with my flats. Preferably though, I'd be wearing boots. In Chicago, with the salt and the snow, all of my flats would be salt encrusted and destroyed by winter's end if I wore them outside.

SmartWool socks are warm though, I can attest to that. I had some before I developed my allergy. They were lovely and toasty.

maryeb said...

I love the Smart wool socks as well. You get a lot of warmth without a lot of bulk. They are a bit more expensive though. I've bought several pairs from (L.L.Bean)and (Athleta).

L.L.Bean offers a number of different thicknesses and sock heights. I pair them with ankle boots. My latest pair is Life Stride brand from Macy's.

Anonymous said...

I get cold feet very easily in the winter, as well. My favorite socks to wear are my thin, wool-blend socks that manage to both keep my toes toasty and appear dressy enough for work.

I have found that Smartwool and Wigwam are my favorite brands so far. You can find them at and other outdoor-type stores. Pass over the thick hiking socks by these brands and stick to their thin wool socks that can work with dressy shoes. They are on the pricey side, but I have been very impressed by the quality of these brands. The socks hold up very well, and I've even noticed that they keep my feet from smelling. Keep your eyes peeled for them at discount stores -I've found these brands for half-price at Nordstrom Rack and Ben Franklin.

Here are a few links that show examples of socks that would work:

Tara said...

I am a teacher in a warm-weather climate, but we do get a few cold days. I like sweater-tights, they are pretty warm and you can get nifty patterns or general black and grey that will look professional.

You can also think about wearing "athleisure" type sneakers. They are pretty streamlined so they don't look like running shoes and they are great for teachers on the move. That way you can wear more regular type socks with them.

Aimee C said...

I wear my snow boots into the office, then switch into trousers socks and my dressy flats once at my desk. Not only does this keep my feet warm, but it gives my shoes a little more life - sparing them from winter's snow and the salt put down on the walks and roadways.

Btw, just discovered fishnet trouser socks. Pairing them in the same color as my flats is my new favorite thing.

Lydee said...

i teach also, and crack me up about the "in case we have to run" part. Yeah, been there, done that! we also make sure we have break away lanyards so we don't get choked. you never know with some kids.

I like my flat boots, flat casual shoes, dressier sneakers and fancy flats. I have found nicer socks to go with the casual shoes, and i love my trouser socks for flats. Of course, I'm always hot when i teach.

gina said...

First, I second the boot recommendation, b/c you can layer whatever warm sock you want underneath without worrying about how they look.

Another option is flat loafers or oxfords with a much higher vamp so socks are only glimpsed when sitting. Or jazz shoes, which are trendy this fall.

Also, I second the smartwool recommendation. I live in those all winter.

Finally, you can get thinsulate socks at ski shops that are very thin and should line regular socks easily. I'd imagine they're relatively expensive. I haven't tried this yet, but friends who ski swear by them.

Unknown said...

Hmm... what about moccasins? The kind with the furry lining should keep your feet warm. I think they look nice with slacks and should be (depending on the style) appropriate for teaching in.