With pants, I wear flats or heels with (gasp!) nude knee highs. Barely any skin shows and it looks like, uh, skin. Just don't buy "sun tan" stockings and you'll be fine.

I go '93 sometimes and wear combat boots with my dresses. Warning: this may cause you to want to listen Tribe Called Quest, Nirvana, etc.

OP here -- thanks for the replies. I meant my dress pants are baggy at the bottom (now that I'm finally used to skinny pants...which means they will be completely out of style soon! ). I like the Express slightly bootcut pants for work -- thanks for the link!

I'm a bit confused by your question. What's baggy--the pants or the boots?

Anyway, when I want to wear my boots under my pants (which I do, 2-3 days a week at least), I wear boot-cut pants. Which is, like, all my pants, actually. (Except one pair.)

Or you can also wear ankle boots.

Geez, men have it so much easier...

So when do you wear trouser socks? Is it okay to wear wedges with trouser socks or knee highs??

Anonymous wrote:OP here -- To PP -- Would love to see a pic of skinny pants that look good with trouser socks and shoes (not at all being snarky, just really need ideas). thanks

With skinny pants you wear high boots, if you need to wear socks. I just wear pumps & flats without socks but commute in uggs.
The other option is ankle boots with socks and dress slacks (not skinny pants)

This gives a good idea of how to pair skinny jeans with ankle boots and a lot of the styles definitely have socks:

http://www.pinterest.com/search/pins/?q=skinny%20jeans%20with%20ankle%20boots&rs=ac&len=14

Whatever you might wear in warmer weather + knee-high stockings.

I wear boots similar to the ones above with wool socks. I can wear them with straight leg pants, but certainly not ankle length pants. It isn't totally perfect for me though. I might have the world's scrawniest ankles, because they are not as close to my legs as those, and the cuffs of my pants sometimes catch on the boot top when I stand up. Have to do a little leg shake or hem pull sometimes.

OP here -- To PP -- Would love to see a pic of skinny pants that look good with trouser socks and shoes (not at all being snarky, just really need ideas). thanks

We're talking about what to wear to work, correct? If so, pumps or ankle boots if you don't want to wear knee-high boots.

There are lots of shoes that are made to be worn with trouser socks, or am I missing something?

Ankle boots that are supposed to be worn under pants (slim at the ankle), with a heel. I like something like this: http://shop.nordstrom.com/S/michael-michael-kors-asbury-bootie/3494470?origin=keywordsearch-personalizedsort&contextualcategoryid=2375500&fashionColor=BLACK&resultback=2587&cm_sp=personalizedsort-_-searchresults-_-undefined_8_D

For pants, I like the Editor pants in the Barely Boot style from Express.

So here's my dilemma -- I am not one of those people who can go without socks with flats anytime before April -- too cold! But agree that socks with flats looks bad.

So all winter I've been wearing dresses with tights and knee-high boots, jeans with knee-high boots, and on and on. Love my boots but what I really miss is wearing my nice black dress pants to work with my knee-high black boots UNDER the pants. But I tried them on the other day and they felt so baggy at the bottom.

So what do you wear to work when you don't want to wear pencil-slim pants with knee high boots showing or a dress. What nice black dress pants can I buy that are in style and what do I wear on my feet until it's really warm out?

Thanks!!