A trip to Boston this upcoming weekend was a somewhat last-minute plan. Since my niece, Morgan, headed up there last year to attend Emerson College, there, of course, has always been an intention to visit her, and my husband and I figured it would be in the autumn or spring because it’s not like New York winters aren’t brutal enough. Boston in winter? No thank you. Yet, it was only about three weeks ago that we made solid plans to head there this weekend. The bummer about fall in the northeast is for as gorgeous as it can be is also about as short as it is, and we get a sparse amount of weekends before the holiday rush and wet, sloppy miserable weather steps in.

Given the somewhat last-minuteness of this trip and how busy things have been, with the exception of a text thread between Morgan, my husband, Frank, and myself — aptly named Wicked Pissah Weekend — the planning between us so far has basically only included must-try food destinations, my noted discomfort being around people who play-act in period garb, that we’re going to force Frank to at least try on a tri-fold hat, and the discovery of that three-story crazy glass globe you can go inside, called the Mapparium, at the Mary Eddy Baker Library. Other than that, there is literally no plan.

It’s not that you need much of an agenda when you go to Boston because the city itself is one big tour of American history. It seems like the type of place where even a random street corner would have some epic past attached to it. The issue with Boston isn’t finding things to do, it’s figuring out what exactly to squeeze into your short visit when you have a laundry list of things to choose from, especially when you have never been before. I know, I am about as shocked as you that I have never been to Boston.


I think the issue with cities you can easily get to is you put off getting to them. Growing up in New Jersey, Boston has always just been right there with me knowing I could always just take a quick trip…that I didn’t. For me, it’s like the Statue of Liberty. I grew up being able to see the New York skyline from my bedroom and now can walk a few blocks to the East River from my apartment and see the Statue of Liberty from the waterfront. Yet, have I ever actually been to the Statue of Liberty? No. I did fly to Boston’s Logan Airport once before getting whisked away to Hingham, Massachusetts while I was still a fashion designer and worked for Talbots and they still had their entire HQ based in that city. If you want to get technical, I have been to Boston, I have just never been to Boston.

So, I’m terribly unprepared and don’t even have the trip really on my radar yet. It’s still in the back of my mind. For someone like me, who loves a good plan, this doesn’t really settle well, but I’m going with it. And, really, my main goal is to catch a glimpse of the life of my niece Morgan, who is one of my favorite people on the planet, living in a city she has fallen in love with as her adopted home city and who has created a beautiful life for herself as a busy college student. I’d much rather see Boston from her perspective anyway and maybe throw in a few historical sites which probably won’t take much effort by us to seek out. Of course, I’ll likely say more than once, “on the next trip, we’ll have to check that out,” which, as long as Morgan is still up there studying, we will have the assurance that we will.


While the trip to Boston is without much of a plan, what is going into my suitcase has been far more considered even though we are only going to be gone from Friday to Sunday morning. The reason for this far exceeds the fact that my brain is just wired to think like this. Northeast weather in Autumn is about as changeable as gas prices, and New England weather is like the mid-Atlantic’s colder cousin. Therefore, it wasn’t so much my preference for being an efficient packer that had me put this much thought into what I would pack as much as it was the erraticness of the forecast that forced me to think about what to pack for my Boston weekend.

Here is what I have set so far.



In order to talk about my packing plan, I should probably bring you up to speed on some of my recent purchases because I plan on incorporating them into what I might bring. You can review my original fall wardrobe plan, which included my shopping goals and planned buys, here. Since that post, I made some purchases, some earmarked and planned and others unintended. This is what I have purchased.



First, I did a huge Quince order and pretty much bought everything that was on my list with the exception of the cashmere turtlenecks which were sold out at the time and recently came back in stock. In addition to the items I had picked to buy, I also got their lightweight puffer jacket, which I love, and some of their comfortable at-home pieces.

All I can say is Quince for the win. If you are hesitant about their cashmere due to the price, don’t be. It’s incredible. However, my two surprising favorite pieces are their Cotton Fisherman Crew Sweater and their Cotton Oversized Cardigan which I have worn to death and are the perfect weights for this time of year. The fisherman sweater is adorable and chic and the cardigan somehow manages to be simultaneously super relaxed but not super sloppy. I have lived in it. The packable lightweight puffer is also fantastic and for 50 bucks, you can’t beat it and I also purchased the navy washable silk tee. I just wish the puffer came in more colors but then realize I probably would have purchased a neutral color anyway.


Next, I shopped on Poshmark and picked up a few sweaters from Vince —my other go-to for sweaters— and picked up two rugby-striped styles. Sorry, not sorry, but you can’t have enough stripes as far as I’m concerned. The Rag & Bone blazer is the one I blogged about a few weeks ago. I purchased two Frank & Eileen Barry shirts (size up if you have a big chest) because I die for their shirts. I bought the Everlane button-down because I continue to be on this ridiculous button-down craze, and I bought a small grey Allsaints crossbody in grey when I realized that I didn’t have a small grey bag. I also bought a pair of Vince high-waist cigarette pants in olive upon noticing I didn’t own a pair of olive pants but have a lot of olive in my wardrobe.


I purchased this very casual orange scarf from Weekend Max Mara because of the whole orange inspiration from my original post. I also loved the idea of wearing an orange scarf with my new grey puffer as a color combination.


I have been dealing with a plantar fasciitis flare-up for the past month and last week it got so bad I was hobbling. I ran over to my podiatrist who shot my foot up with cortisone and taped it to relieve the pressure on the tendon. It’s feeling better but when I thought about being on my feet for this trip, I immediately thought about making sure I had the most comfortable sneakers possible. This needed to go beyond my oh-so-comfortable M.Gemis and Aquatalias.

I popped over to the Taos website to pick up a pair of their Plim Soul sneakers which is what we recommend to every client heading on a trip that will involve walking. These were a recommendation from my assistant Rachel who, while pregnant, walked into a shoe store and asked for the most comfortable sneakers available. She wound up wearing nothing else her entire pregnancy. Taos makes great shoes and sneakers for anyone looking for comfort but is particularly great for those with plantar fasciitis. These sneakers are incredibly comfortable and exceptional for the feet.


Every now and then I’ll grab a random photo of myself wearing some looks, nothing fancy and sometimes I don’t even have makeup on, but they will give you an idea about how I have been incorporating my new items.


This hasn’t been as straightforward, not because I don’t have anything to pack, but because of making sure comfort, and a variety of temperatures and needs are covered. Two days of travel should be easy enough but it might rain one day, there will be lots of walking, and some fun dinners out, and the temperature will swing from cool mornings to mild afternoons and colder evenings. Layering and clothing that covers temperature swings are important. So for now I have three small capsules pulled and will probably make a game-day decision when I am packing, but having some options framed out will make it easier when I am ready to actually ready to throw things in my suitcase. It didn’t take a long time to plan and will save me a lot of time in the end.


boston weekend

Capsule 1 is a navy, grey group with splashes of camel and red. This was the first one I created. I got hung up on packing my Saint James Breton and Stella McCartney blazer to use as my daytime outerwear piece. I also plan on packing my Max Mara anorak and Quince lightweight puffer in case it does rain or gets cold. My puffer folds into itself and takes up little room, so it’s nothing to pack and as of now there is rain in the forecast for Friday. So in every capsule, I have included these pieces.

Also included in every group are my grey Aquatalia loafers which are incredibly walkable and weatherproof should I not want to wear sneakers or it’s really raining hard because my Taos sneakers aren’t waterproof. I am also packing weatherproof Aquatallia booties in case it gets cold at night. I always pack a small crossbody and have added the grey Allsaints crossbody to the group along with my bright favorite Longchamp bag which I use as my carry-on and when I need a larger bag. I am also throwing in one pair of non-jeans pants and chose my Akris Franca pants for this group.


Boston Weekend

The reason I didn’t feel entirely settled with the first group was that when I went to Toronto in June, I built a navy capsule and was feeling like I wanted a change. So I built this capsule with the same strategy above in mind. I started with a new favorite sweater, a yak blend rugby stripe that I wore recently with a pair of jeans, my tan Aquatalia booties, my camel coat, and a camel scarf on a dreary day in early October when it was freezing here. With my new Vince pants, I got inspired to build this taupey-grey, olive group with a splash of bright orange and a little teal.

In terms of color, I am feeling way more inspired by this group as compared to capsule one but do have concerns that my flannel Rag & Bone blazer might be too heavy if the forecast is slated to be warmer than it is now. But I do love this palette and I can get a lot of looks from it.

In terms of a capsule, not all the pieces work together but all the pieces work together, meaning, nothing is an orphan. When packing for such a small trip, the goal isn’t necessarily to get as many outfits as possible in terms of length but in order to have enough options from what you are packing to cover all the needs that may arise, and in this case, the needs are varied due to temperature fluctuations.

To illustrate all the different ways I can spin these pieces, I have created different outfits. As you will see, I will be able to meet whatever comes up from bad weather, to colder weather. I can dress for a dress-casual dinner, or a day of walking, and can layer up and peel off layers as needed. By the time the day comes when I pack, I may pull back on actually putting some of these things in my suitcase because I clearly have more than I need, but as a starting point, I at least know I have my bases covered.


boston weekend

I created a hybrid capsule last which married the parts of each capsule It does involve an additional pair of shoes, my light teal Gia flats, which I would only wear out to dinner, but when you have the most perfect shoes for a scarf which would also play really off burgundy in an interesting way, it’s hard to resist. So I’ll probably throw them in, just because. Adding burgundy added more complexity to the group, and I paired olive with navy and used grey as a mid-tone shade. And like the capsule above, there is more here than I need and I will likely reassess the need for all of it when I am packing my suitcase. Here are just some of the looks I can create.

boston weekend


Just throwing things in a bag for a trip is an option, as is throwing in way more than you need haphazardly just to be sure. However, a strategy like this is usually just a guarantee your suitcase will be overloaded and you won’t have what you really want. Taking a few extra minutes to plan it out more fully like this can not only make it possible for you to put in your suitcase to cover your needs but there is also a greater chance you will be excited about what you will bring. While all these things may not even make it into my suitcase, taking the time to create these looks gave me some ideas for some looks I can wear in the future.

Certainly, you actually need the right things in your closet to begin with, which is why a capsule you pack for a trip should simply be an offshoot capsule of what already mixes and matches in your strategized wardrobe. Had I not had a closet of well-thought-out and directed pieces in my closet to work from, I never would have been able to build these capsules so quickly and easily. Think macro, work micro.

Autumn is the perfect time for a quick getaway and I hope these tips have helped you more strategically pack your weekend bag or suitcase for a trip away.