What to do and Wear in Boston this Winter

Hello and Happy Fall!

As we transition into the colder weather and brace for the snowy months ahead, it's important to remember and appreciate the beauty in winter and the holiday season. There are numerous activities to do in the city to put people in the festive mood, and in this post I will share with you all what places to visit, and more important, what to wear to those locations.

  • Ice Skating in the Boston Common is the ultimate winter activity in the city. Whether you're with your friends, family, or significant other, ice skating under the stars is a magical feeling. Tons of people show up daily at the Frog Pond between December and March for a fun, romantic time in the city at an affordable price. When getting dressed to go ice skating, the key is to be warm. Since you'll most likely be renting ice skates you can wear thick fuzzy socks so your feet don't freeze. To add a touch of chicness to your look, wear a pair of tapered wool trousers are sure to keep you stylish and warm. Top layering is imperative in keeping yourself warm, and a simple way to do that is by wearing a tank top as a base layer, followed by a snug fitting long sleeve shirt. To finish off the look wear a chunky pull-over sweater and a thick insulated coat that hits you in your mid-thigh. Wear gloves, a hat, and a scarf as you please!
  • Holiday Tree Lighting Ceremonies take place at different locations in Boston, however the most popular ceremony occurs in the Commons. It is the perfect way to kick off the month of festivities - taking place in early December. Tons of Bostonians join together in the park to enjoy live music, food and snacks, along with games. It is a simple way to get out of the house and enjoy the city while also meeting new people. When heading to the tree lighting, I would consider wearing a black fur coat over a nice red glossy blouse and a dark colored pair of high rise trousers (skinny or straight). Wearing a comfortable pair of leather booties and a red beret will add a nice touch to this fashionable look. 
  • Performances in the Theatre District are always charming to view if your are not a fan of cold weather and outdoor activities. Numerous holiday related shows take place in the district, such as Elf, Mannheim Streamroller, Jingle Ball, and tons of companies perform The Nutcracker - just to name a few. Tickets sell out quickly, and can get steep in price so it's important to do your research ahead of time. For an outfit outin the theatre district, I would take the more formal route by wearing a fitted mid-length dress with a colored coat. A modest heel, a pair of tights, and some festive makeup will have you feeling confident and beautiful for any holiday show.
  • Basketball Games in TD Garden make for a fun, entertaining, casual, and laid-back night with people you love. Whether you're a sports fan or not, it's always interesting to watch games and get excited with the crowd while eating your favorite snack. This winter activity is perfect if you don't want to get dressed up or go outside. Wear your favorite team's jersey over a snug hoodie and a good-fitting pair jeans. Most importantly, don't forget to bring your team spirit!
  • Top of the Prudential Center Views are something that can't be beat in the winter time. Experience breathtaking sights of the city on the 50th floor of the Prudential Center with a 360 degree view. Since it will be colder out, there will barely be a haze over the city giving viewers an optimal perspective over Boston. Top of the Prudential is the best place to get an aerial view of the city, and if it's snowing when you're there you can get postcard-perfect pictures. Wearing a nice pair of long flowy culottes with a simple sweater and a structured leather jacket is a perfect outfit to wear to this location. There is also a restaurant called "Top of the Hub" located there, so you can sit and have dinner afterwards if you really want to have a fancy time. 
  • Historic Taverns and Irish Pubs scattered throughout Boston are a great place to sit, unwind, and warm up on cold nights. Go during happy hour to get discounted drinks and eat delicious food to kickoff the weekend and meet new Bostonians. Some of the pubs in Boston have been around since the American Revolution which gives them a nice charm. Going to pubs is a Bostonian tradition, and one of the best times to go (other than on Saint Patrick's Day) is in the winter. Try wearing a pair of flare jeans with a simple blouse, some jewelry and heel booties to look effortlessly stylish.

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