New York is known for many things: great architecture, amazing museums, stylish people, and of course, out-of-this-world restaurants and bars. In New York, you can pop into almost any neighborhood and find a Michelin-star spot somewhere. If I’m being honest, this is one of the reasons I ditched Los Angeles for the Big Apple. I’ll admit I’m something of a foodie. Sitting in a fabulous New York restaurant and sharing delicious food and cocktails with friends is at the top of the list of ways I love to spend my time. 

But once you snag your ultra-exclusive, how-the-hell-did-you-get-that reservation comes the inevitable question: “What am I going to wear?” This was precisely my dilemma when I finally got a reservation at the very cool cocktail bar Jac’s On Bond after months of trying. So the first thing I did was start outfit planning.

I mean, you can’t show up to one of New York’s chicest watering holes in a so-so outfit. While planning what to wear for my Saturday night out at Jac’s, I started thinking I should make a guide of foolproof looks to refer to the next time I can’t figure out what to wear. So I began researching and found four outfits that are so good you can wear them on repeat.

Keep scrolling to see which outfits I’ll be rotating through for my upcoming dinner dates.