I'm just branching out into very wide legged pants and barrel jeans and jean-like pants (the latter from Uniqlo, in a light color). I'm not a heels-wearing girlie, more into boots and sneakers. I am getting the pants/jeans all shortened, because they are huge and I'm 5'5". So I guess the first question is, how short should I get them? Right at ankle bone? I know the barrel jeans/pants might be a bit ruined by shortening them, but Idk what else to do.

And for shoes/socks - I would love your BWT input - low sneakers with no-show socks? Chelsea boots that disappear into the pant legs? Something totally different?

Thanks!

Over the past year or so, I've started transitioning out of skinnies in favour of straight- or wide-leg pants, almost all of which are a bit cropped (think these or these). My lifestyle is pretty active — I don't have a car, and bike my toddler to daycare and back every weekday, bike or walk to work and to run errands, etc. During the summer, I did this in flat sandals or almond-toe ballet flats. Now that the weather is changing, though, I really need to trade them in for some sort of foot-covering flat shoe that will still look ok with wide leg pants!

Do you have any suggestions? I think wider pants look pretty good with heeled ankle boots (I have some Rachel Comey Mars boots that look quite nice with the ones I have, for example), but I really need a flat shoe or boot for every day and the ones I have look... off. I've tried to look at online stores for inspiration, but most of these pants seem to be modelled with heeled boots, flat sandals, or barefoot! Help!

I don't have any kind of dress code for work, but as an academic in her mid 30s I want to look like I'm trying to be presentable, at least. I live in England, in a place where snow is not a realistic possibility except maybe around Christmas.