What to Wear in Boston – My Looks

May 7, 2018September 25, 2018 Location: New York

I’m so sorry I’ve been MIA lately, but I’ve been so busy at my Master’s and with side projects that I haven’t been having so much time to sit down and take a couple of hours to write for the blog. But let’s correct that right now to clarify your questions on what to wear in Boston!

Also read: Most Instagrammable Places in Boston

My trip to Boston was really short. I spent a weekend in the city in September as it was transitioning to a Fall weather. I had the challenge to take not a carry-on, but a BACKPACK (!!!), so my total number of outfits totaled TWO.

Facts you need to know

If you are going to explore the city and walk a lot during the day, you’ll probably go straight to dinner to, then, go back to the hotel and sleep. Boston is a great city to do that because the restaurant scene doesn’t require the attire that cities such as Los Angeles do (I actually find this to be very common in East Coast cities). But going from your tours to dinner also require your outfit during the day to have that little extra.

Anyways, it is always helpful to plan ahead and check the weather forecast for the days you’ll be in town. In my case, it was super nice, sunny and warm and I could use dresses and skirts (or A dress and A skirt).

Tip:

If you have limited space, take one bottom that matches several tops. That way you can have variety and not need a lot of space.
You’ll walk a lot in Boston. So, once again, if you don’t have space, ONE pair of sneakers will do the job for you.

I took one super stylish denim jacket from Katya Dobryakova that upped the level of both my looks and broke their ice. I would suggest you do the same and take one statement piece you love (preferably a jacket or coat, since you can take it on your hands, rather than on the backpack).