I'm flying home this weekend, so I face somewhat the same dillema
Sadly... I wear for comfort, and comfort only when I fly.. I suppose this time may be different because once I arrive home I'm meeting up for a bite to eat and drinks.
But for New York in the fall, for four days... a blazer or two is a must, and a couple of sweaters. Pack ONE jacket or coat that will go with everything that you're wearing.. and the same with the shoes/boots, try to downgrade those. That's always wear I have a problem... I always like to pack several pairs, and those take up more space than anything!