I've always been a huge fan of the classic American style. Boots, field jackets, and denim shirts are always a good recipe when it comes to layering up for cold days in the city. I purchased the field jacket pictured last last Winter from Brooks Brothers, and it has been a staple in my wardrobe ever since. I paired the jacket with a sweater from Banana Republic, and a denim shirt by Ralph Lauren. The pairing of solid colors gives the outfit a very simple, but elegant look that has a timeless appeal.
A pair of Ralph Lauren spectacles are a daily essential. After wanting round frames for quite some time I finally stepped out of my style comfort zone and tried something new. To step farther out of my comfort zone I recently bought an Indiana Jones-ish hat from Topman that I have fallen in love with. The only downside to this hat is how easily the wind can/will knock it off of your head as the brim is in essence a sail.
To finish off this outfit I threw in some wing-tip boots by Johnston and Murphy, and some grey trousers from Brooks Brothers Red Fleece collection. The tapered cut of the pant sits perfect at the top of the boot when cuffed. A large pet-peeve I have is when there are multiple breaks (pants bunching at the top of the shoe), simply cuffing your pant, or having it tailored for a specific shoe is a great way to improve your style.