I wear them with jeans, leggings, cords, skirts - anything really, if it is raining. For you true city dwellers who walk to work, I can't imagine not having these. One very important thing to note - I wear these with fleece boot socks in chilly weather, but a snow boot they are not! The rubber gets super cold and then freezes your feet - I learned that the hard way. Since I heard it might be another frigid winter, check back for my fav snow boots, as soon as I find them.
It can feel challenging to put together an outfit when it is raining. I won't even go into the hair issues when its raining!!! But it definitely presents an outfit challenge. There are certain pants, shoes, jackets that you just can't wear in the rain. So I tend to go for the basics in dark colors so water spots don't show, and then pair with a fun trench and fun umbrella! I have a trench very similar to this - Macy's Jessica Simpson - I love the sheen. And of course a leopard umbrella. Quick note on the trench - if budget is not an issue I would have a standard issue black or khaki trench and a fun print or bright color for spring, but if you have to pick one, go for one you can wear all the time with anything.
Here is what I decided to wear tonight - out to dinner with friends, in the rain. I know I just spent paragraphs talking about the Hunters - but I'm in black booties here. I know I won't have to walk much and these shoes can take the rain. Instead of my trench, I chose my faux leather jacket - polyurethane is quite waterproof. And a scarf to take the chill off. I am out of practice with my modeling - this will have to do.