We often get sartorially bogged down in winter. After a few weeks of sub-freezing temperatures, we don't care how good we look or how well anything goes together - we just want to get warm and keep piling on the layers.
I have good news, ladies and gentlemen! It is, in fact, possible to stay warm and still look respectable and even sharp, despite the weather. Here is Gerry, in a very weather-appropriate layered outfit, that is also interesting and classy.
The core of this look is the jacket with a pattern that combines neutral colors (black, brown and beige) with a punctuating orange stripe and a subtle pale blue one. Combining blue and orange seems counter-intuitive, but it works here, because orange is allowed to dominate in the form of a warm rust-colored vest worn over a pale blue broadcloth shirt. The effect is further enhanced by a striped pocket square that also picks up the major colors of the outfit.
The khaki pants are a nice traditional base for the look, but still look neat and crisp due to the flat front and the cut that works with Gerry's figure. It would be a shame to let down such a great outfit with scuffed sneakers or clumpy boots. Dressy half-boots worn over warm wool socks make for a classy yet practical option. Throw on a nice coat, scarf and hat - and you are ready to go!