Boston Packing: What I Wore & What I Bought
From NYC to Boston in just four hours, one scenic Amtrak ride transports you from the bustling streets of Manhattan to a city rich with charm and American history. As a first-time visitor, I didn’t know what to expect, but I discovered Boston to be coastal calm and collegiate energy. For a spring weekend getaway, it did not disappoint.
Daytime Looks
All-American Ensemble
I kicked things off with a true all-American outfit featuring Ralph Lauren. I wore a navy half-zip polo paired with my Lucky Brand vintage straight leg jeans, and to top it off, a red silk scarf with navy and white accents. Preppy and relaxed look for Masters Sunday.
Rainy‑Day Casual
When getting ready for a shopping day at South Market, I swapped into a navy vintage Polo crewneck layered over Lululemon leggings, high socks, and my go‑to Hokas. My Pap’s oversized leather bomber kept me dry as I ducked into Sam Adams Brewery & Tap Room to sip seasonal brews with the boys.
Evening Looks
For dinners out:
For night, I leaned into city edge with a pair of cargo pants from BDG and a chain-detailed asymmetrical crop top I picked up from a boutique in Soho. Leather mule booties kept my feet dry through puddle, although cobblestones were a different story. We savored dinner at The Atlantic Fish Company, indulging in their famous clam chowder and a decadent lobster roll. Afterwards, I draped my jacket casually over my shoulders and headed to The Beehive for a night of live jazz.
One of my favorite nighttime looks was a pleated sage button-down from Natori, styled with my vintage jeans and boots. I took it up a notch with a bold makeup look and fresh waves from a Dyson blowout (Thanks Liv!!). In an instant, these daytime staples morphed into the perfect night‑out ensemble. After a quick train ride into the city, we enjoyed a delicious dinner at State Street Provisions—and, of course, couldn’t resist a cannoli from Modern Pastry on the way back, because Italian pastry stops in Boston are non‑negotiable.
The One Thing I Had to Buy
Every trip, I treat myself to one special purchase—this time it’s the Coach Essential Chain Card Case wristlet. Its slim profile holds my apartment keys, cards, ID, and a little cash, and the chain strap lets me go hands‑free through NYC without a bulky bag. It’s a functional everyday piece I know I'll use for a long time. Plus, my old Coach card case was falling apart after 5 years!
Unboxing video: https://www.tiktok.com/t/ZP8jsUbYw/
Link: https://liketk.it/5bi5h?product=cc9e78a4-1a4d-11f0-8016-0242ac110016
Final Thought
Packing for Boston gave me the perfect excuse to mix vintage staples with fresh spring pieces. I loved styling looks that balanced practicality with personality, from rainy day layers to elevated night-out moments. A little city grit, a little coastal charm, and just enough room in my bag for a new wristlet.
