Night Out

Where: Angel's Share, New York City

Penguin Houndstooth Wool Blazer
Buy It Now at Park & Bond, $225 

Jil Sander Quilted Overcoat
Buy It Now at Barneys, $639 

Ovadia & Sons Pistachio Flannel Trousers
Buy It Now at Ovadia & Sons, $198 

Cole Haan Air Monroe Loafers
Buy It Now at Cole Haan, $198 

Stussy Deluxe Ettinger Wallet
Buy It Now at Stussy, $350

A night out on the town is great for new couples and old couples, you can both discover new places or revisit old haunts from when you first started dating. It's best to hit up places that can facilitate conversation, like the classy Angel's Share bar in the East Village, a cocktail lounge hidden behind a Japanese restaurant. As long as it's just the two of you, getting seated shouldn't be a big deal. Keep things elegant with a subtly patterned blazer and warm flannel trousers. Should you decide to barhop, a good overcoat is key, as well as shoes you can walk in. Thankfully these Cole Haan loafers have a Nike Air sole. Also, if you've still got the same wallet from college, it's time to upgrade. Since you'll be paying for the tab, chances are she'll be seeing what you keep your cash in, so make sure it looks as good as you do.