Anchie, I'm offering some additional tips/ ideas for urban winter walks for you. I posted some on Chris's great thread, but there I described my current winter wear for walks in a fairly temperate suburban environment; here, I'll tell you what I used to wear for a much colder and more urban setting.
Like you, I wasn't big on true gear for my walks in an urban environment. Just didn't feel right. (I do wear much more gear now that I am walking in a different place with different kinds of roadways.)
Here's the kind of outfit I tended to wear in Eastern Ontario's cold winters. I walked in all conditions. Even a few ice storms (I don't advise it.)
The kinds of items you'll need include:
1. Comfortable but fashionable footwear with a good tread. I highly recommend seeking out some kind of sneaker boot for this purpose. Either that, or an excellent low heeled chelsea boot. Examples in Finds.
Make sure the footwear is warm enough or has enough room for good wool socks.
2. Wool socks! :)
3. Underlayers. I preferred to wear my regular casual clothes, more or less, with some adaptations. But of course you can also wear gear if you like. Anyway, beneath my regular clothes I often wore -- camisole or longer sleeved base layer, sometimes with long underwear -- heattech or similar.
4. Clothes. I usually wore jeans and a wool or cashmere sweater. I think I'd be uncomfortable in office wear -- a bit too restrictive. But there are certainly some wool trousers and even jackets that could work.
5. Coat. For me, usually a puffer. I have various weights for various purposes. I also have a "gearish" rainproof coat with cozy lining that I could wear in warmer temps if it was wet.
6. Scarves, hats, gloves, sometimes mitts.
I grew to love cold-weather walking. It's invigorating. And it makes the winter go by so quickly.
Here I am in Kingston, late last February.