Fall is a difficult season to plan for. You can wake up to a warm dry morning and finish the day suffering from Trench foot. That's why I think that all of your fall footwear should feature some sort of water resistance. Each of the boots I will feature here include a rubber sole.
I personally prefer a thin rubber sole over its leather counterpart because I'm not a weather man. I don't know if it's going to rain this afternoon or not and I'd rather be dry than not dry.
1. The Chelsea boot
The Chelsea boot is an intimidating boot for most people. Yes it looks very fancy but as long as your pants or jeans are tailored and not billowy then you should be able to pull it off. This dapper pair is from Jack Erwin (www.jackerwin.com) and features a thin rubber sole to keep you dry.
2. The Wingtip Boot
The wingtip boot can be as dressed up or dressed down as you like. It looks especially great paired with some tweed pants, the chunkier material is perfect for the cooler fall weather. This pair is from Johnston & Murphy (www.johnstonmurphy.com) and features a cushioned insole that makes long days walking around the city feel like nothing at all.
3. The Mountain Boot
It can be warm or cold during the autumn months and for those cold days you should definitely have a warm pair of boots. UGG (www.uggaustralia.com) lines a lot of their boots with a wool lining that keeps your feet warm but doesn't make them sweat. These Boysen TL boots are super comfortable and extremely light weight, the perfect combination for cold weather. They'll be practical from Fall all the way through to the Spring.
4. Cap-toe Military boots
Boots like these are rugged enough to wear all weekend long and stylish enough to continue wearing to the office on Monday morning. Once again these boots include a rubber outsole that makes them practical for wet and dry weather. Thursday Boots (www.thursdayboots.com) have created an extremely comfortable, well made boot for a great price.