How about oxfords? Can't recommend a brand but you can definitely wear them with socks x

I've had exactly the same problem and have found some great shoes in Clarks. They do varying widths and cater for most tastes. I recently bought their Nara Sigh Boots which fit under trousers and look smart but also go with skirt suits. They're a bit mor exciting than a plain boot. Their collection is one of the best I've seen this year and our guaranteed good quality.

http://www.clarks.co.uk/find/D.....s-20334023

I am on the hunt for a fun pair of jazz shoes/tie-up oxfords for this exact purpose. Othewise I just buy longer pants and wear heeled oxfords/booties.

In the winter I mostly wear boots or booties. You can wear sleek knee-high boots under dress slacks; provides an extra layer of warmth.

I also have spectator/oxfords, but they have a heel, similar to this shape (but dark gray metallic):
http://www.zappos.com/stuart-w.....ay-flannel

I wouldn't mind getting a pair that are flat, something along the lines of these:

http://www.zappos.com/stuart-w.....irror-calf

or these
http://www.zappos.com/steve-ma.....ck-leather

These aren't flat, but they are cute!
http://www.zappos.com/sam-edelman-echo-black-grey

I am also on the lookout for some super simple version of flat black booties to play the role of winter ballet flats. I like these, but not their price:

http://www.shopbop.com/stunt-d.....ze-viewall

Till then, I will probably do as Shiny suggests and wear my flat tall black riding boots under pants.

Ooh, Shiny -- the Sam Edelmans you linked to presented a link to this one: http://www.zappos.com/beautife.....?zlfid=111

Way out of my price range, but check out the "Black/Grafitti" combination. Be still my heart...

Great ideas everyone! I think that flat boots sound like my best and most versatile option. I'm going to check into Clarks as I've had good luck with that comfort brand before and I really need comfort!

Angie, if you are reading...I'm hoping you do a winter shoe roundup!

Such great suggestions from the lasses!

Chelle, I’m afraid I am not good at offering budget solutions for fussy feet. My feet are VERY fussy and invariably the shoes and boots that work out are better-end (apart from Me Toos and Doc Martens). Winter shoes are especially expensive. But you can’t go wrong with brands like ecco, La Canadienne, Sudini and Aquatalia – if the shoe or ankle boot is comfortable. If you wear the heck out of a pair of expensive peds, the cost per wear whittles down to nothing. I guess that’s my philosophy – having fewer but very well made and gloriously comfortable shoes.

I have several pairs of boots, ankle and tall, but need a pair of comfy low heels -
Can i wear these with socks?

http://www.zappos.com/n/p/p/7552888/c/1153.html

What do you think of them?

Clarks, Born, and Sofft are all very comfortable shoes for me. Try some knee-high boots under your pants. I do that and find its perfectly warm.