For the transition between the sweltering heat and the bone chilling cold, you need to have some tricks up your sleeve in the footwear department. Heavy duty boots will be to warm and dense for a breezy day in October and your driving mocs will lack the much needed insulation in any weather that reaches into the near freezing department.
|Exhibit A: Casual.|
You need something that bridges the gap between shoe and boot, that can work in any type of weather that this upcoming season decides to throw at you. With that in mind, look for chukka boots, an ankle high boot that is going to be your savior this fall/winter. They come in many shapes and sizes, but the overlying theme is their pseudo-hybrid combination of a boot and a shoe that you can wear in just about any weather and for almost any occasion. Granted they are a casual shoe, in the current men's wear environment, it's not a bad idea to try and pair them with a suit and see how it looks.
|Exhibit B: Dressy.|
Keep the constructions simple with your choices; you don't want a crazy amount of extras making them less versatile. Instead, you should be looking for chukkas with rich leather and deep color that will get better every time you wear them. A nice mid calf leather in a rich brown, a rich suede in a mahogany tone, or a silky nubuck in a sandy shade. Now pair them with jeans or some cords and let the rest of the outfit come together around them, because a good outfit starts from the ground up.
Check in tomorrow for a fashion piece that deserves your consideration and next Wednesday for another closet necessity!