Valentine’s Day is only a week away, and it’s time to get your outfit set for the biggest date night of the year! But just because you will be surrounded by hearts and cupids, doesn’t mean you have to wear the expected red ensemble. I have date night styles for hot Chicago and Boston spots that you can wear all year long.
Chicago has plenty of cozy date spots, even in the freezing weather, but some of my top lesser known but still hot spots would be perfect in any weather for a first date, a first anniversary, or just a casual drink with friends.
North Pond Restaurant has been located in the heart of Lincoln Park for over a century, with a great view of the Chicago skyline and a Valentine’s Day menu that includes lobster and hazelnut chocolate. Play off the natural setting of the spot with a floral printed dress from Elizabeth and James. You can wear it with a leather jacket, tights and pumps for the winter, or with a great cuff bracelet and sandals in the spring. You don’t want to go over the top with a printed dress, but a great statement piece of jewelry like a bracelet or cocktail ring is a perfect conversation starter.
Another sexy spot is The Monarch, which will be having a to die for tasting menu for Valentine’s Day. This Wicker Park restaurant is nice for a first or second date, or fun enough for just drinks with the girls, so go for an upscale but still casual look. I love this Vince printed top with leggings and knee high boots from Steve Madden. Over the knee boots are the latest fashion rage and take any outfit from work day to date night. And you can give the whole look a really special touch with this Revenge-inspired double infinity necklace from Helzberg Diamonds.
If you’re a Boston native, one of our favorites is Drink, where the craft cocktails will knock your stilettos off. The industrial space, once an old warehouse, needs a tougher look, like these leather leggings from Anthropologie. Add a feminine touch with a silk wrap shirt and chandelier earrings. The dim lighting and neighborhood atmosphere will give the whole evening a comfortable feeling, so the earrings will add a little extra sparkle.
Last but certainly not least, Post 390 has two date spots in one! On the first floor, The Tavern is perfect for a group or more casual date night so go for this sleeveless suede top from Neiman Marcus with skinny jeans and a delicate charm necklace (my personal favorite, also from Helzberg Diamonds). If you make your way upstairs to The Dining Room, it will be a more refined evening, perfect for your first Valentine’s Day together. To make it one to remember, try this neon dress from NastyGal and keep the look more casual with these Anthropologie cage booties.
No matter what the location or the event, remember that your date night outfit should be one that makes you feel comfortable and confident. When you feel your best, there’s no way the date can go wrong!