What to Wear for Date Night – Winter in Chicago

We recently went to Old Pueblo Cantina in Lincoln Park for a weekday date night. This restaurant just recently opened and it was delicious! Highly recommend ordering a cheese crisp as a starter, which is one of their signature dishes. We also really enjoyed the mango margarita we had.We were plenty full with the chips and salsa, cheese crisp and a split order of tacos.

I wore a pair of ripped-hem cropped flare jeans, a cardigan as a shirt with my favorite pair of Marc Fisher boots. The boots are on sale right now and are a really good deal. I’m really enjoying how skinny jeans aren’t the only cut of jeans that is in right now. Also love the trend of cardigans as tops. The jeans in this picture are old Abercrombie jeans, but I did link a similar pair from Madewell. Abercrombie has definitely made a comeback and their jeans are great.

Would definitely recommend trying out Old Pueblo if you’re in Chicago. It would be good for drinks after work, date night or a casual lunch! It is also right next to Sweet Mandy B’s, which is a delicious dessert place that has excellent cupcakes, cookies and other sweets. I would also recommend checking out Abercombie for jeans. They tend to almost always have a sale running and they have tons of different styles. Another thing that they’ve added is curvy denim as well as the ability to see the jeans modeled by multiple different sizes, which is great. I’ll link some of my favorites down below. Hope you enjoy!