Ice Skating

Where: Rockefeller Center, info here

Schott G-1 Cowhide Leather Bomber Flight Jacket
Buy It Now at Schott NYC, $1,125

Outlier Woolback OG Chinos
Buy It Now at Outlier,  $220

Wallace & Barnes Everett Check Flannel Shirt
Buy It Now at J. Crew,  $98

Carharrt Watch Cap
Buy It Now at Arvada Surplus,  $9

A classic date that can't go wrong and gives her an excuse to hold your hand for an extended amount of time. Add in some hot cocoa and ample amounts of whiskey and Irish cream, and you've got a fun, affordable date on your hands. Keep warm with a lined leather jacket and pants made for the weather. These Outlier chinos are lined in comfortable merino wool. Add an extra layer with a thick flannel shirt, and protect your head with a beanie.