You can be sure you'll look modern and classic in a white and black vertical striped dress shirt and grey dress pants. Why not take a more relaxed approach with footwear and complement your look with dark brown suede chelsea boots? While it can be a bit difficult at times to look stylish in extra cold, it's getups like this that prove it's quite doable. Wondering what you should wear as you get into your 40s? This pairing is a good illustration.