Winter in Florida is unlike most other corners of the country. It can get rather cool, but for the most part it hovers around comfortable. Allowing the finest of outfits to be worn sans infinite layering. Unfortunately, as it is Florida, fashion is not always the top priority on everyone's list. It seems as if the norm are flip flops, cargo shorts and some Affliction/Tap Out/Ed Hardy type shirt. Looks really cool, and it takes guys to a whole new level of bad ass.
Everyone has their own style and if it's working; fantastic. However, there are many better options out there. Below is a short example of a great look good for a 'day' outing in comfortable weather. All of the needed items can be obtained through Bonobos. Their service is highly recommended. Cheaper options are available as well, but you can't beat the quality to price ratio. It rings true.
Here's the outfit; you can try any mix of the below items with different colors and experiment as you wish:
The Pants: The Rawhides
The Shoes: Finn Lace Ups Dark Brown
The Shirt: Fall River - Dark Wash
The Sweater(s): Grey or Navy Wellington
The Blazer(s): The Lewis or The Clark (Both on sale!)
Anyway, I'm out of here...