Garb: Pennywise
Save Khaki Nylon Short Jacket ($295).
RRL Slim Fit Jeans ($300).
It: Novel by Stephen King ($19).
Loro Piana Cashmere Beanie ($450).
Ami Leather Gloves ($270).
Kapten & Son Watch ($99).
Puma Tsugi Sneaker ($119).
Paul Smith Wood Handle Umbrella ($150).