APC grey new standard jeans

t-shirt and shoes

other monochromatic clothing.

Wear them with:

Slim black ankle boots
White dress shirt
Monochromatic black/white/silver striped tie
Black or charcoal suit jacket

- or -

Black ankle boots/black chucks
Black or dark gray cardigan sweater; either zip-up or button-style
Solid black, white, or gray tee under. Or, use a brightly colored tee as the focal piece of the outfit.

What's a good pair of ankle boots for around $100-200?

Yeah, gray jeans take a bit more work to pull off. I have four pairs in various shades of gray - from about the shade you posted, all the way to a pair that is nearly black.

As previously stated, monochromatic color schemes work well with gray. Also, light pink looks really good, as do other pastel colors (baby blue, lilac, light yellow).

You should definitely get a cardigan sweater. I have about 6-7 in the zip-up variety, and one really thick button up cardigan with a nice collar on it. I wore some variation of the cardigan sweater 4 days out of the week this fall and winter.