Traveling Light: A Winter Packing List for a Weekend in Boston

Opening up my suitcase - err, backpack - and sharing everything I packed for a weekend in Boston.

Although I’ve always considered myself a “weekend travel blogger,” I suspect this year was the one where I truly took the most true “weekend” trips of all, departing on Saturday and returning on Sunday (in the past, I’d say I probably traveled more Friday-night-to-Sunday, or on those occasional long weekends).

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Packing for these overnight flyaway trips is a breeze when you decide to simply pack one outfit per day – and you get bonus points in my book when those garments could combine to form additional outfits if needed, especially when you’re flying budget airlines like Spirit (not that I’m speaking from experience or anything…).

I took this concept and applied it to packing for my recent trip to the Boston area, which was quite easy to do considering we had a fairly relaxed itinerary of museum hopping, dining, and exploring. As always, I like to dress for the destination, letting it inspire the pieces I bring, and for Boston that meant a backpack full of classics. I reached for my favorite natural fibers in neutrals, and soon Michael and I were off, budget airline-approved backpacks in tow.

With plenty of room to spare for my current knitting project plus an impulse coat purchase, here’s everything I packed for a chilly early-winter weekend in Boston and Cambridge:

BOSTON PACKING LIST

A collage of everything in the author's backpack for her trip to Boston — Ivory Cashmere Sweater℅ [review] | Black Cashmere Sweater | Wool Coat℅ [review] | Blue Denim | Wool Pants℅ [review] | Pajama Top | Pajama Bottoms | Sunglasses℅ [review] | Beanie | Belt | Loafers℅ | Convertible Bag℅

BOSTON OUTFITS

Alyssa wears a black sweater and pants with a camel coat — Black Cashmere Sweater | Wool Pants℅ [review] | Wool Coat℅ | Sunglasses [review] | Convertible Bag℅ | Loafers℅

Saturday

The first day of a trip is always so exciting – and even better since we had a little extra time to get ready in the morning before our 9 a.m. flight (normally we fly out around 6 or 7 a.m., but this is what was offered and I relished that extra bit of sleep). An all-black outfit made things easier still, while an elastic waistband kept me comfy all day long. I topped the whole thing off with a classic camel coat for an extra touch of luxe, elevating the outfit a little for our dinner with a business casual dress code. This outfit formula appears in many forms during my travels, and there’s a reason I keep reaching for it.

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Alyssa wears a white sweater with blue jeans and a camel coat — Ivory Cashmere Sweater℅ [review] | Wool Coat℅ | Blue Denim | Belt | Loafers℅ | Convertible Bag℅

Sunday

Unfortunately, Sunday brought a downpour that I was not expecting (of course I checked the forecast beforehand, and of course it was wrong), but I made it through the day with the help of a few great accessories: my waterproof loafers (use code WAYWARD10 to save 10%), a cashmere beanie stashed in my coat pocket, and a borrowed hotel umbrella. Back indoors, this look was perfect for exploring the Gardner Museum and enjoying a brunch cocktail at Krasi before trekking to the airport to fly back home – truly, it’s hard to beat a white cashmere sweater and blue jeans.

THE TAKEAWAY: PACKING FOR BOSTON IN THE WINTER

Alyssa wears a white sweater, blue jeans, beanie, and loafers in a T station in Boston — Damp in clothing, but not in spirits

November and December are Boston’s rainiest months, so I suppose I had an authentic travel experience! If I had to pack for this trip all over again, I’d probably pack the same items plus a raincoat for the downpour (there was room in my backpack, after all).

Looking for more packing list inspiration? Discover what's in my suitcase each season: Spring | Summer | Fall | Winter

Other than the rain, I felt quite comfortable for the entire trip, both in regard to temperature and atmosphere. Style in Boston and Cambridge spans from casual (there are so many college students in leggings) to preppy (think cardigans unironically draped over the shoulders), and a camel coat was the perfect topper for this trip. A great coat makes all the difference in an outfit, doesn’t it?

As you’re prepping to pack for Boston, I’d note that I didn’t see many outfits that felt particularly edgy or avant-garde; even in the city’s fashionable shopping areas, people’s overall style felt very classic and traditional. I suppose that leaves even more goodies on the racks at thrift shops for the rest of us to take home…

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Questions for you:

Have you ever been caught in the rain while traveling?

Do you like to travel with a little room in your luggage, or do you take advantage of every inch of space?

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