If you’re getting ready for a trip to Boston, and you’re not sure what to pack or wear, you’ve come to the right place. Having been to the city countless times in all four seasons, I’m excited to share with you all the tips I’ve learned along the way, and what to wear in Boston to fit in with the locals while staying comfortable.
In this post, you’ll find packing lists and guides, seasonal tips, outfit ideas for each season, and also suggestions on what NOT to bring, so you go into your trip feeling prepared to explore this beautiful and charming city.
Ready to get started? Let’s go!
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Why trust my advice?
Hi there! If we haven’t already met, I’m Sam, and it’s really nice to meet you. Welcome to New England Wanderlust! I live locally in the northeast, and have been exploring New England for over 20 years now. I continue to travel through this region to report back on my favorite places, new discoveries, and regularly update the information in my posts. I created this website because I truly love this area, and everything is based on real life experience – you won’t find any AI here! Sit back, relax, and enjoy getting real advice from a real person who continues to travel throughout New England all the time 😊
What To Wear In Boston – Style Overview & The Essentials
↑ Links to current styles I’m wearing (or similar) to above: Knit sweater tank | Adidas sneakers | Everlane high-rise jeans
Boston is a very casual city, like most places in New England. In fact, Boston proper is home to over 30 colleges, with more than 60 in the greater Boston region. Why is that good to know? Well, you’ll see a lot of college kids around, which tends to keep the vibe pretty relaxed and casual.
But those in Boston who aren’t in college still keep their style casual. You’ll see a lot of jeans, sneakers, baseball hats, and sports gear – like Red Sox and Celtics apparel and such. And in general, folks don’t really dress up too much, unless they’re going to work, or an upscale event of some kind.
Here are the must-haves when packing for a trip to Boston:
Comfortable sneakers – the most important thing. If you take anything from this post, let it be this! Boston is a small, walkable city, and especially for visitors hitting up the top sites, it’s very likely you’ll be walking almost everywhere. Between this, and the fact that the city has lots of uneven brick and cobblestone sidewalks, most everyone wears sneakers.
I most-often wear my Adidas sneakers because they have a very casual look while being super comfortable, and a little trendy. I have the Collegiate Green Sambaes that I tend to wear in the fall and winter, and the Light Blue Gazelles (pictured above), which are really perfect for spring and summer.
Jeans and tops – This will be your basic outfit while out and about, especially during the day. Jeans, sneakers, and a comfortable top (depending on the season) is the best way to stay comfortable while exploring the attractions and sites. I have some outfit ideas for you later in the post if you need them 😉
Outerwear – Depending on the season you’re planning your visit during, you’ll want to pick the best outerwear for your trip. Since Boston experiences all four seasons, this is super important. I’ll go more into seasonality later in the post, but in general, you’ll likely need a good, waterproof rain jacket for the spring and fall, a warm parka for the winter, and maybe a light jacket (or even just a sweater) in the summer, depending on how hot or cool it gets that day – or if you’re planning to go out onto the water.
Daypack or purse – Depending on your preferences and what you need to carry around with you during the day, you’ll want to have something that holds what you need. I usually wear a crossbody purse, and after years of searching, my absolute favorite is the Large Meadow Crossbody from Leatherology. I love this one because I personally prefer a smaller bag, but need it to hold everything I use throughout the day. This bag perfectly balances both of those things, and also, has a classic look so it goes with every outfit I’ve ever worn in Boston. I have it in both black and camel, and did purchase the longer strap separately to wear it as a true crossbody – just FYI 😉
I also really like these crossbody sling bags from Beis, which hold a water bottle. They’re more casual, but really perfect if you don’t need to carry around too much. They’re big enough to fit your wallet, keys, lip balm, and a few other small things, but that’s about it. However, having the water bottle holder is honestly so convenient! Especially on a hot day exploring the city. I use this bag a lot when hiking and going for longer walks in the city, and my crossbody purse for everything else. But you don’t necessarily need both.
Pro Tip For All Seasons!
You don’t always need to pack fancy going-out clothing, depending on your plans. I hardly ever wear anything out to dinner or in the evenings that I wouldn’t wear during the day to explore the city, unless I’ve got tickets to a show or an upscale restaurant. If your itinerary doesn’t include anything that requires nicer clothes, don’t stress too much about packing any. Remember – Boston is casual!
What To Wear & Pack In Boston In The Summer + Outfit Ideas
Now that we have the essentials out of the way, let’s talk about specific seasons, and some outfit ideas – starting with summer.
Summer in Boston is hot and humid most of the time, and it’s one of the most popular times of the year to visit the city.
Late June through August is when you’ll experience the best weather with the fewest days of rain, but you’ll want to anticipate temperatures in the 80s°F, sometimes getting up to the 90s°F, with humidity that can make it feel like it’s 100°F. I’ve planned weekend getaways to Boston when it’s been 98° with high humidity, so it definitely happens! It’s more common in July and August, though, and you’ll usually experience temps in the 80s.
Early to mid September is when the temperatures begin to slowly cool down, but it will definitely still feel like summer. You’ll get random hot days where there’s still a risk of it feeling like 100°, but you’ll notice evenings beginning to cool off more, and daytime highs not being so … well … high 😊
Packing Essentials For The Summer:
Sneakers: I’ll probably drill this point home a few more times, but just to reiterate that even in the summer, you’ll want a good pair of sneakers to stay comfortable while walking around.
Sandals: These are also good to pack just to mix up your footwear. I’ll often pack sandals in the summer for shorter walks and evenings out.
Shorts: If it’s forecasted to be really hot during your summer trip, I’d recommend at least one pair of shorts. I usually wear linen shorts in Boston, but pack whatever you’re most comfortable in.
Tees and Tanks: To stay cool during hot weather, I’d focus on packing tees and tanks that will pair well with whatever shorts you bring. I’d be sure to keep it casual enough that you can pair these with sneakers, and then have at least 1-2 outfits that will also work with sandals for going out to dinner to dinner.
Pants or Jeans: While jeans aren’t always the best choice for the summer, they’re pretty versatile if the weather isn’t super hot. I do wear jeans in the summer with a sleeveless top and sneakers if the humidity isn’t too bad, and have been comfortable. For longer pants that aren’t denim, linen ones work very well, too.
Dresses & Skirts: Always a good choice to stay cool in the summer months! I usually pack one sundress to wear in the city for a summer getaway, in addition to shorts and tees. I keep them casual enough that I can wear them with sneakers for walking around. If you pack any skirts or dresses, I can’t recommend these thigh-saving shorts enough, which prevent your thighs from rubbing together when it’s hot out. I always wear these under skirts and dresses in the summer.
Hats: Since Boston is a pretty windy city being that it’s close to the water, I’d leave your bigger straw hats and such at home, and opt instead for a more casual baseball hat. These stay on a bit easier if it’s windy, and you’ll also fit in more with the locals 😉
Boston Summer Outfit Ideas
Below you’ll find some photos and collages of outfit ideas, which are how I pack for my trips during this time of the year. Of course, adapt it to your own style!
↑ Links to current or similar styles to above: Navy and white striped button tanks | Blue gauze shirt | Linen pull-on shorts | Raffia purse | Leather crossbody purse | Striped t-shirt | Sneakers
↑ Links to current or similar styles to above (that are different from previous collage): Cream linen pants | Knit sweater tank | White gauze shirt
What To Wear & Pack In Boston In The Fall + Outfit Ideas
Fall in Boston is pretty awesome, and not just because the fall vibes are on point. The weather is usually pretty mild, and it’s really comfortable for exploring. There’s usually a slightly higher chance of rain than the summer season, but the colorful leaves and cooler temperatures more than make up for it.
In late September to early October, the temperatures can sometimes still feel like a mild summer day, and the weather doesn’t usually start to feel consistently cooler until mid October – so keep that in mind. Once you’re into mid October, expect daytime high temps to hover around 65°F, but this can vary a lot from year to year, and even day to day. It’s best to check the forecast before packing.
Packing Essentials For The Fall:
Rain Jacket: Not only will this help to keep you warm on cooler days, but it’ll also work to keep you dry if it does rain. And since Boston is one of the windiest cities in the U.S., it’s much easier to wear a rain jacket than carry around an umbrella. I really love this one from Eddie Bauer. It’s completely waterproof (you don’t want water resistant – it really should be waterproof).
Duck Boots: For many of the same reasons above, duck boots are what I wear the most in Boston in the fall season (in addition to sneakers) – especially if there’s rain in the forecast. Bean Boots work really well, but sometimes can be a little slippery on wet brick sidewalks. But these Sperry Saltwater Duck Boots have a bit more grip. Both are great options, and will serve you well in Boston!
Sneakers: If there’s not a ton of rain in the forecast, I’ll wear sneakers most of the time instead. If you’re looking for a sneaker that’s waterproof, I also love Vessi sneakers. I got these for both my husband and I when we went to Scotland, which is notoriously rainy and wet, and our feet stayed dry the whole time while wearing these. This will allow you to save the room in your suitcase and basically just wear the one type of shoe your whole trip.
Jeans: In the fall season, I primarily wear jeans to stay warm and comfortable. I almost never wear dresses or shorts this time of the year.
Long Sleeves & Sweaters: Depending on the temperatures forecasted for your trip, you’ll want to coordinate long sleeves and sweaters to wear during the days and evenings. I most often wear stripes and neutral sweaters, but you can pack whatever you have that will work 😊
Cool Weather Accessories: You’ll want to pack things like a beanie, a scarf, and/or gloves and mittens, depending on how cold it’s going to be. At the very least, I’d pack a beanie to keep you warm at night, especially if you’re planning any fun evening ghost tours.
Boston Fall Outfit Ideas
Below you’ll find some collages of fall outfit ideas, which are how I pack for my trips during this time of the year. As mentioned, these can be adapted to your own style.
↑ Links to current or similar styles to above: Light blue button down shirt | Striped sweater vest | Adidas sneakers | Sperry Duck Boots | Yellow waterproof rain jacket | Leather crossbody purse (both colors) | Fisherman knit sweater | Boston baseball hat | Everlane high-waisted jeans | Striped sweater | Trench coat | Burgundy knit beanie | Vessi waterproof sneakers
What To Wear & Pack In Boston In The Winter + Outfit Ideas
↑ Coat pictured above: From LOFT (currently on sale)
Probably the most important season to pack correctly for in Boston is winter, and that’s because winter weather in the city can be all over the place. You could experience anything from blustery snowstorms and frigid temperatures, to mild & sunny days, to cold rain.
The absolute best thing to do to pack appropriately for your winter trip is to check the forecast a few days beforehand to see what the forecasts are calling for. While they could still change, this is the most accurate information you’ll get before leaving for your trip.
Some general notes to give you an idea on Boston winter weather:
December can be more mild than the rest of the season. Lately, it’s been more rainy in December than snowy, but snowfall is still very possible.
January and February are the coldest months that are the most prone to snow and snowstorms.
March does see the occasional snowfall, but is warmer than January and February, and often sees a lot of rain or freezing rain.
Keep in mind, these are all generalizations, and things can definitely fluctuate from year to year, especially with global warming impacting the winter months the most in New England.
Packing Essentials For The Winter:
A Good Winter Coat: I’ve gotten parkas from Eddie Bauer, L.L. Bean, and various places over the years, and my favorites have been from Eddie Bauer, simply because the quality is similar to L.L. Bean, but they tend to run more sales throughout the year. The best all-around parka for New England I’ve found is the Sun Valley Down Parka, which comes in different colors. I like that this one goes down to your mid-thigh for added warmth, and also has a faux-fur hood. However, the Mountain Classic Sherpa-Lined Parka from L.L. Bean is also a fantastic and high-quality option.
Second Coat Option: If it’s not forecasted to be super cold during your visit, you may find a heavy parka to be too much for exploring the city. You can either pack two coats (depending on how long your visit is), or opt for a lighter wool-type coat. I got this one from LOFT last year, and loved it for a winter trip to Boston. The color looked great in photos, too, and it kept me pretty warm. I also have a wool coat from J.Crew, and they come out with similar styles every year that are perfect for a winter city getaway.
Warm Waterproof Boots: I most-often wear my Sorel Out-N-About ankle boots in Boston during the winter, unless it’s super cold. These keep my feet warm, are waterproof, and are easy to walk around in without being clunky. The name for this style is really so perfect because I wear them everywhere else when I need to run errands in the winter when it’s cold and slushy outside. However, if there’s a lot of snow and very cold weather predicted, I’ll wear my Sorel Caribou boots. These have a bit more warmth and insulation, and are higher to protect your calves from snow.
Chelsea Boots: If the weather is decently dry, and you don’t think you need wintery boots, I sometimes pack Chelsea boots for my winter trips. These are just a bit more stylish, and work especially well for going out to dinner. Just make sure they’re flat so you can comfortable walk around in them.
Cold Weather Accessories: This time of the year, hats and gloves/mittens are necessary! You’ll definitely need to pack these for your winter trip.
Warm Clothes: For clothing, I most often wear jeans in the winter, paired with sweaters and layers underneath. One of my staple sweaters is the L.L. Bean Fisherman Knit sweaters, which work well anywhere in New England. I often pair them with a lightweight turtleneck for a classic look, and added warmth. The tissue turtlenecks from J.Crew are awesome for layering under sweaters. As of writing this post, they’re currently out of season, but they tend to come back every year. I’ll keep an eye out and update accordingly 😉
Numi Undershirts: These sweat-proof undershirts are a newer discovery that allow me to re-wear sweaters on my trips. I tend to sweat a lot in the winter because of how many layers I’m wearing while walking around, and these lightweight undershirts soak up your underarm sweat, and are super thin and undetectable under your sweater. They work so well, that I now own 5-6 of them. They’re one of my favorite packing hacks for the winter.
Boston Winter Outfit Ideas
Here are some photo collages of my typical outfits when I travel to Boston in the winter:
↑ Links to current styles or similar to above: Blue coat | Leather purse (both colors) | Winter ankle boots | White knit sweater | Blue striped sweater | Fisherman knit sweater | Light blue parka | L.L. Bean Sherpa Parka
Psst! I also have an entire post on visiting Boston in the winter, if you’re looking for ideas on things to do during your trip!
What To Wear & Pack In Boston In The Spring + Outfit Ideas
Boston in the spring is a pretty underrated time to visit, in my opinion 😉 The weather is definitely a bit all over the place, but I really love the blooming spring trees and flowers all over the city. Weather is just unfortunately unpredictable this time of the year, so this is another season where it’s very important to check the forecasts a few days prior to your visit.
The spring season, of course, brings a lot of rain in Boston, and you can typically expect 9 days of rain per month in April, May, and June (with early June usually having more rain). Temperatures average in the high 50s°F and low 60s°F this time of the year, and evenings tends to stay pretty chilly.
In general, expect anything from freezing rain to warm and sunny days. It really just depends.
Packing Essentials For The Spring:
I typically pack very similarly between the spring and fall seasons, so I would refer back to the fall packing section. Things like the rain jacket, duck boots, sneakers (or waterproof Vessi sneakers), and warmer layers will all work well in the spring season. You may be able to get away with lighter layers, depending on the weather during your trip, so things like blazers and tees may be perfect for your itinerary. But pack warmly if it’s forecasted to be chillier.
Boston Spring Outfit Ideas
In the spring, I tend to wear slightly brighter accent colors than in the fall season, incorporating more blues and such into my wardrobe, versus burgundy colors. But generally, I pack similarly to the fall season, as mentioned. Here are some outfit idea collages to help you:
↑ Links to current styles or similar to above: White knit sweater | Trench coat | Light blue Adidas | White Adidas with green stripes | Cream envelope purse | Navy blue purse
↑ Links to current styles or similar to above: Yellow rain jacket | Light blue striped sweater | Vessi waterproof sneakers
More of my posts you may enjoy:
- My Perfect 3-Day Boston Itinerary
- Spring In Boston
- Where To Find Cherry Blossoms In Boston In The Spring
- Best Boston Food Tours Worth Your Time & Money
That’s A Wrap On What To Wear In Boston!
And there you have it! All my tips on what to wear in Boston for your upcoming trip. The key takeaway is to dress comfortably and casually, paying attention to the seasonality, and checking the forecast a few days prior. New England style in general is grounded in classic pieces that all work well together, so it’s usually pretty easy to streamline your packing. Happy travels! 😊
