Trust me, getting genuine leather at this price is a coup, but it's not impossible. Don't waste your time with faux/pleather/man-made/vegan if you can get the real deal.
In case you are don't know where to start, Target, Endless.com, and 6pm.com are great sources of leather shoes at a budget price.
For your budget shopping pleasure, here are some great real leather options for boot season for under $50...
Target Karima Leather boots ($49.99):
Somewhat masculine, on trend, and look comfy.
Target Kamischel Suede boots ($44.99)
For so much suede (typically impractical in inclement weather) these look pretty durable with the lug sole and sturdy construction. I'd have them weather treated. Several other colors available.
Target Kachiri Leather boots ($49.99):
These are a perfect, unadorned take on the riding boot. The shape is similar to many (much more expensive) Frye boots. Also comes in cognac.
Dollhouse Zatty boot ($37.99):
Fun, slouchy details and a sleek wedge.
Volatile Quill Boot ($48.83):
The two materials add some interest to an otherwise fairly plain over the knee boot.
Sketchers Lunacy-Palomar Boot ($43.99):
These aren't my thing, but I can see them working with a biker chic outfit or even a flirty skirt.
Kelsi Dagger Lace-Up Ankle Boot ($43.42):
Naughty Monkey Rock Out Boot ($42.50 for black, $49.47 for red)
Another suede option with some cool buckle details.
Enzo Angiolini Keylyme Bootie ($39.43):
Super sharp for the office. Also comes in taupe suede.
Clarks Ruby Glimmer ($47.30):
Very good quality and high on comfort for an awesome price.