Looking for Fall/Winter Shoe Advice

I am looking for advice on a great pair of shoes for the colder weather.

• I'm looking for either a boot or a moccasin of some type.
• I really like these Clymer boots by Rancourt in all the colors. http://ift.tt/1jcCPwQ
• The weather where I live will be mostly dry, occasional rain and light snow rarely.
• My budget is about $300
• I am planning to wear them with my normal everyday outfits, I pretty much dress like this guy. I am wearing them casually, to school, shopping, going out with friends, etc.
• I like items with a youthful look, as I am only 19.

Any advice is appreciated!

Looking for Fall/Winter Shoe Advice