I took this trip a few months ago and at this point SF is sliding into spring weather, but given how ephemeral the Instagram feed is, I decided I’d throw everything onto an article here. The individual outfit captions probably repeat some thoughts I’ve voiced in the original instagram captions, but I didn’t get a chance to really review the capsule for the trip as a whole, so here we are. You can scroll to the end to read takeaways if you’re not interested in the individual outfits.
My previous inclination when packing for trips was to bring a bunch of things that are as utilitarian as possible, no matter what the destination of the trip. This usually resulted in me wearing what appeared to be the same outfit every day as I packed mostly things like a softshell jacket and a few variations of leggings and skinny jeans, which was no fun because I was basically wearing the same thing during the whole trip. It was also unnecessary because many of my travels are to perfectly good cities with maintained sidewalks and functional public transit and air conditioned buildings, and I didn’t really need to dress so utilitarian every day (although comfy shoes are always a good idea if you’re going to be walking a lot).
So for this 10 day trip I wanted to pack some things that would result in outfits that
- looked good and were also something I’d wear in my usual life,
- had some variety,
- and obviously were suited for the weather and activities of the trip.
The weather in Boston during the time of my trip varied over around the low 20s to mid 40s F, with some sun, a little snow, and a little rain. I was traveling with my boyfriend to visit his family over the Christmas holidays and we were mostly going to be doing casual touristy walking things (mostly indoors, but taking public transit from place to place), though there would also be some slightly more formal activities including watching a performance of The Nutcracker at the Boston Ballet.
Being from the SF bay area where it usually doesn’t dip under 40F and there’s really not much of an actual need for cold weather accessories, I decided I wanted to take this opportunity to have some fun wearing wintery accessories. I had a white beanie with a faux fur pom-pom and a red and white fair isle patterned scarf that I wanted to really have pop, so I decided to stick to a black and white color palette. But then to prevent getting too sick of my clothes, I made sure to pack a variety of types of bottom pieces that would create a few different silhouettes.
I also wanted it to fit mostly in a carry-on. I normally travel only with a carry-on, but since we were also lugging a bunch of gifts with us in an extra checked bag, I had a bit of extra leeway to use the extra space there.
What I Packed
Here are all the “outfit items” that I packed, loungewear and thermal layering not included (click the image to view the full res in a new tab):
This is a screenshot of the Airtable base that I use to inventory my wardrobe and track my outfits. See the Wardrobe Tracking page for more details.
I wasn’t sure how the temperatures listed would actually feel like, so I decided to err on the safe side and bring two pieces of outerwear I could layer in case I felt really cold. I wanted to at least bring my nice coat since it would look smarter for some of the more dressy activities.
- black puffer jacket
- black faux fur hood wool-blend coat
I originally packed just two sweaters and intended to swap between them, but I ended up buying a sweater at the LL Bean store. We don’t have brick and mortar LL Beans in California, so I wanted to take the opportunity to try on a few things that I’d had my eye on.
- beige lambswool mock-neck sweater
- cream oversized wool-cashmere blend balloon sleeve sweater
- cream fisherman cable-knit sweater*
This is the part that I think really made this capsule. 3 very different bottom silhouettes that I could rotate through, as well as three different textures.
- black culottes
- black faux leather midi skirt
- black straight-leg jeans
I would have been perfectly fine wearing the pleather midi and one of the sweaters to see the ballet, but personally I really enjoy the experience of getting all fancy to go see a performance like that, and I wanted to have something to wear that was different than my everyday outfits.
At the time this velvet dress was a recent thrift find, and the novelty hadn’t worn off yet.
- black velvet sleeveless maxi dress
I was hoping to just bring the pointed-toe boots, but while they’re pretty sturdy they’re not exactly meant for inclement weather, so I brought my trusty docs. I’d heard anecdotes that people found they were terrible on salted sidewalks but I didn’t have a problem with that at all, though to be fair I was only seeing the short term results.
- Dr Martens 1460 combat boots
- black patent leather pointed-toe lace-up boots
I picked plain base items so I could focus on accessorizing more than I normally do. Accessories take up less space in luggage than clothes anyway.
- black leather belt
- tan leather belt
- rust headband
- gold headband
- cream cable-knit pom-pom beanie
- multicolored pom-pom beanie*
- rust beret
- red fair isle scarf
- green tassled cowl scarf*
Still wanted to feel a bit festive even with all the black and white, so I made sure to bring my green bauble earrings and some red floral earrings.
- green bauble earrings
- red floral drop earrings
- gold horn fake gauges
- gold rings
- gold petal earrings
- gold double layer celestial necklace
- gold leaves stretch cuff
- ribbed thermal tights (2)
- thermal leggings (2)
- thermal long sleeve top (2)
- chunky socks
- gray sweatpants
- navy university sweatshirt
I resisted the temptation to bring a clutch.
- tan leather crossbody purse
See DIY shitty Gorillapod for taking outfit photos while traveling for my photo setup.
Day 1: Mostly traveling all day. This was a bit of a disheveled hair and sweater at the end of the day. I wore all my bulkiest items and regret wearing the jeans on the plane with a belt. So uncomfortable! I think this the second time I wore the scarf and I really feeling how festive it was ✨🎄✨
Day 2: I can’t even remember what we did on this day tbh. I think this was the day that included a stop at the LL Bean store as well as meeting up with people for meals. Normally I don’t think of the puffer as a fashion item, but I liked it combined with the pleather skirt because of all the texture. I was off monochrome black/white outfits for a while because most of my wardrobe was mostly “flat” fabrics like cotton jersey, but this reminded me that those can still be interesting. This was one of my favorite looks of the trip.
Day 3: It was rainy and warm (like 50F) that day, and I was low-key disappointed I couldn’t wear the velvet maxi dress and pointed boots because we did a bunch of tourist stuff in Salem, MA, but not a bad look overall, if a bit basic. I liked the tougher vibe with the structured coat and docs, though I think it could have used a necklace. I’m wearing one of the extra-warm heattech tops as a shirt here.
Day 4: I cannot remember what we did on this day anymore either. It involved walking around outside though and I definitely wore the puffer jacket on top of this.
Day 5: I think I just wore this to go out for food and watch a movie. Tbh my ears were really cold because it was particularly windy that day, but I lived. Normally I am very wary of layering sleeveless items over long sleeves, especially white ones, because it’s so easy to get into “my mom made me layer this for modesty” territory which I’m still recovering from (anyone else wear a white turtleneck underneath a frilly princess style dress when they were in kindergarten? Anyone?). I think here the accessories make the whole thing seem intentional enough, although this isn’t one of my favorite outfits ever.
There was an unphotographed second outfit on this day which involved the same sweater with jeans and the docs for a trip to the Zoo Lights night event at the Zoo New England. It was an okay small zoo, but the event was extremely crowded and there were not very many animals out. It was the first time I saw rock hyraxes though so that was interesting.
Day 6: Christmas eve!
Day 7: Spent Christmas at boyfriend’s aunt and uncle’s house. This was an okay outfit even though it was sort of a gradient that got slowly more rugged/casual toward the bottom. I think it would have looked better with the pointed-toe boots.
Day 8 day: This was truly a vacation that involved doing a whole lot of nothing because I can’t remember what we did this day either. I’m okay with that. I do too much stuff normally anyway. Getting some turn of the century newspaper boy vibes here but I dig it.
Day 8 evening: Went to go watch The Nutcracker at the Boston Ballet. I’m glad I decided to give this dress another wear, but I think that it’s just a tad too dowdy for my taste. The straps are too wide for it to come off as slinkily loose, and it’s not quite fitted enough to be bodycon, and it’s a little small at the bust causing some gaping near the armpits. I wore the wool coat and green scarf over this.
I wore these rings literally every day of the trip. I usually enjoy wearing more bling when my base outfit is more muted.
Day 9: Worn for going to a bunch of the Harvard museums (the natural history and anthropology museums, which were really great) and then ice skating. This is about as basic a cold-weather outfit as you can get but I did like how the hat, scarf, and gloves were all patterned. Wearing one of the thicker thermal leggings over tights instead of actual pants. Feels a bit unbalanced as all the visual interest is in the top half.
Day 10: Return travel. Definitely my chic-est plane outfit to date and way more comfortable than jeans.
Things I liked
- My plan to keep decisions simple with a black and white color palette jazzed up with accessories went as I hoped – getting dressed was easy in the mornings.
- The green scarf! I really love how easy it was to wear the cowl neck style. When I wear normal scarves, even infinity styles, I’m always fiddling with them. It had a heck of a lot of static though and causing the tassels to float straight out whenever I took my coat off.
- Also the hats. Man, I love pom-pom beanies but I don’t wear them much back home since it just doesn’t get cold. I should make more of an effort to wear them next winter.
- Thicker thermals could double as normal clothes.
Things I’d change
- I would not have packed a whole extra sweats set just for loungewear! At home in the SF bay area, we literally never turn on our heat and just pile on sweaters as the thermostat drops. In Boston, since the outside at night was closer to 20F than 40F, the heat was turned on and it would have been fine if I’d just brought shorts and the tee. The sweats were pretty bulky and it would have been nice to have that free.
- On that note, I ended up having THREE “outfit” sweaters which was nice while we were there, but took up loads of space in the carry-on on the way back. To be fair one of them was bought there and I wasn’t absolutely sure that I would be purchasing anything there, but for future winter trips I would only want to have 2 sweaters packed even for 10 days.
- Didn’t end up wearing the rust headband, and I wouldn’t pack headbands for any cold weather trips in the future because I found that I really preferred having a hat on outdoors. Headband + hat = no go for me.
- I wish my formal dress had long sleeves that I could layer a full thermal shirt under. I did consider wearing one of them under since they were black too, but it looked a lot less fun. I ended up just wearing the coat over it since I figured we wouldn’t be outside more than 15-20 minutes anyway and it was okay, but could have been a tad more comfortable. But still, it was good to know that in that sort of ~30-35F weather I can suck it up for a little without a sweater layer under a coat.
- Boots are so heavy! I would try my best to at least only bring one pair of boots (and preferably wear them on the plane), even if I had another pair of shoes.
- If I’m going somewhere much colder and windier than this, I would seriously look into ordering some functional ear muffs. My ears got pretty cold! I don’t know if it’s my hair type or head shape or what, but I found that both beanies tended to slide up my head and leave 2/3 of my ears exposed which really bit when the wind picked up.
Overall I was really happy with how this turned out. I overpacked a bit, but it didn’t really cause any problems besides perhaps being a bit more tired schlepping stuff around during the air travel days so I think it was okay. I’ve ended up really liking the purchases I made at the LL Bean, too. I don’t think we’ll be going to Boston every winter, but we will definitely be returning with some regularity, so taking some notes this time should make subsequent trips easier.