Best shoes
9 best shoes for Boston in December
highs of 42°F, lows of 28°F, 12 rainy days — here's what to put on your feet.
Why these shoes for Boston in December
Boston in December averages highs around 42°F, lows near 28°F, 12 rainy days.
Boston’s historic cores have uneven brick and cobble — skip thin fashion flats. Expect long walking days in Boston: cobblestones reward grippy soles and ankle support.
Plan on two pairs — one built for the weather extremes and a lighter backup for evenings and dry stretches.
Our picks focus on waterproof boots, traction sneakers, packable rain shoes — enough range to cover day-to-day walking without overpacking.
How many pairs?
Pack two pairs
Recommendation: 2 pairs
- Primary: waterproof or water-resistant pair for wet sidewalks.
- Backup: drier/lighter pair for dinners and transit.
Best waterproof boots for Boston in December
Matte
Matte Black Waterproof Chelsea Boots
Sleek waterproof Chelsea boots with a pull-on elastic gusset and grippy rubber sole for wet sidewalks and airport security. Low shaft and…
Handles ~12 rainy days
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Stone
Stone Grey Waterproof Hiking-Lite Boots
Low-profile waterproof boots in stone grey with light hiking construction tuned for cities, not summits. Solid grip for hills and wet pla…
Handles ~12 rainy days
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ForecastStyle pick
Black lace-up hiking boots
Ankle-height hiking boots in black with a waterproof finish and cushioned insole. Supportive on trails and easy to style with outdoor-adj…
Handles ~12 rainy days
Shop on Amazon →Best traction sneakers for Boston in December
ForecastStyle pick
Black City Traction Walking Sneakers
Black walking sneakers with subtle multi-surface traction for cobblestones and wet plazas. Dark palette and low profile stay city-appropr…
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ForecastStyle pick
Navy Cobble-Ready Traction Sneakers
Navy cobble-ready sneakers with understated lug depth for European old towns. Stable toe box and flexible midsole for uneven streets.
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ForecastStyle pick
Black-and-White Waterproof City Trail Sneakers
Waterproof low sneakers in black and white with city-friendly traction for wet sidewalks and short park trails. Packs flatter than boots …
Shop on Amazon →Best packable rain shoes for Boston in December
ForecastStyle pick
Navy Packable Rain-Ready Knit Sneakers
Navy waterproof knit sneakers that compress in a tote when not worn. Sock-like fit with sealed construction for tropical wet seasons and …
Handles ~12 rainy days
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ForecastStyle pick
Grey Quick-Dry Waterproof Low Sneakers
Cool grey waterproof low sneakers designed to dry fast after puddles. Neutral color hides splash marks on multi-day wet-weather itineraries.
Handles ~12 rainy days
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ForecastStyle pick
Black Waterproof Traction City Sneakers
Black waterproof city sneakers with multi-surface grip for rainy hills. Dual-purpose pair for wet cobbles and long museum days.
Handles ~12 rainy days
Shop on Amazon →Wear them with these outfits
Climate-matched looks for Boston in December.
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FAQ
Are waterproof shoes necessary in Boston in December?
Yes — with roughly 12 rainy days in the month, waterproof or water-resistant shoes are a strong bet.
Do I need boots in Boston in December?
Yes — average lows near 28°F mean insulated boots will keep your feet from freezing on the walk back to the hotel.
Can I wear sandals in Boston in December?
Not really — highs around 42°F are too cool for open shoes on most days.
Can I get by with one pair of shoes in Boston in December?
Two pairs is safer — wet cold months punish a single pair. Pack a weather-ready primary and a dry backup.
What about dressy dinners in Boston?
Most cities accept clean sneakers or light boots for smart-casual dinners. If you have a black-tie night, pack one dress shoe and wear your walking pair on the plane.
Any tips for packing shoes for Boston?
Wear the bulkiest pair on the plane, stuff socks into the packed pair, and use a shoe bag so damp soles do not ruin clothes. Pack a thin spare pair of socks for rainy days.
Do cobblestones or hills change what shoes I need in Boston?
Yes — cobblestones punish thin soles and tall heels. Choose grippy walking shoes or boots with ankle support.