First I see that it is going to be in the 30's and 40's and likely rainy so that will dictate my first direction. This posting is about travel so I'll address drawers and why in another post later but make certain that you have enough and call it a day.
Travel Day Shirt: I like to wear loose fitting clothing all of the time and have a preference style of shirt for winter travel.
1) I really don't like the feel of sweater on my torso on a long day...it makes me itch, but love how it makes me feel. The perfect solution is a nice fitting Underarmor stlye (this one is Reebock) athletic shirt.
2) Occasionally the airplane is a little warm and life is about comfort. Once in your seat if you get too hot, you could pull off your sweater and be comfortable in your athletic shirt. This isn't my preference, but it is a nice option to have.
Pants: I am a jeans kind of guy and have tried them all. I like different jeans for different reasons. This pair of jeans are nicely worn in (but not worn out) Levi 527 charcoal, boot cut, low rise. They just fit perfect. Roomy in the thighs and crotch but snug enough to stay up when the TSA requires you to remove your belt. The charcoal color makes you look just a little more dressed than blue but you are still in denim.
Shoes: I actually have a favorite pair of shoes for travel. They are made by Kenneth Cole and the only pair of KC shoes that I own. I think that they are 10 holers (5 holes per side for strings). I have had them for many years and hope they last for many more. There are a few reasons that I love these shoes.
1) They are comfortable (I could run a mile in these things if I wanted to)
2) They are innocuous ( they aren't in style nor totally unstylish)
3) They can pass for dress shoes for one day in a pinch (not evening wear but to a decent restaurant)
4) If you absolutely have to take your shoes off at the airport, they come off fast and they don't require retying for some odd reason. They of course should be retied to get maximum comfort but I could just as easily walk a mile without them being tied and they never feel like they are falling off. They hug my feet loosely untied.
Coat: Selecting the right coat for travel can be really tricky. I see a lot of different climates and do a lot of different kinds of activities. So I understand the importance of the right coat for me in any circumstance. One with style. So what did I choose for this trip? A have a really nice Ride Cell 10 snowboarding jacket in dark blue herringbone that fit the bill perfectly.
Sunglasses: I never leave home without sunglasses. They are possibly one of the most important accessories any person can have. UV rated and Polarized! My choice for this trip are my Persol 2762.
Well, let me give you a hint. The eye doctors say that the sun can do more damage to your eyes in the day time when the sun is less visible because your pupils are open and you aren't squinting to keep out the light. Want to avoid cataract surgery (or at least defer it? Sunglasses...and not from the Dollar store!
Luggage: Who doesn't want fine luggage to show how successful they are when they travel? Me! Of course I have a really nice Magli duffel that I travel a few hundred miles in my car and want to treat myself but from miles of road in the airport I have learned one really good lesson.
I have a Lucas roller bag with me on this trip and it's very much like the ideal bag (an army duffle bag) but with rollers. It has some cool pockets to keep your stuff separated and it rolls nicely but it has two really important qualities.
1) It's beautiful bright blue nylon and looks like no one else's.
My carry on: Yes my carry on is my most important bag. I have a number to choose from but my go to bag is a red and black Tony Hawk backpack.
Travelling in style is a personal thing. Find your style, but keep it tasteful. You don't have to standout far to be outstanding!