Best shoes
9 best shoes for Portland in December
highs of 46°F, lows of 37°F, 17 rainy days — here's what to put on your feet.
Why these shoes for Portland in December
Portland in December averages highs around 46°F, lows near 37°F, 17 rainy days.
Portland rain and neighborhood hills favor waterproof everyday sneakers or light boots. Plan for solid daily walking in Portland: hills make cushion and grip matter more than fashion alone.
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 Portland in December
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 ~17 rainy days
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ForecastStyle pick
Black Lined Waterproof Winter Chelsea Boots
Black waterproof Chelsea boots with thermal lining for wet, freezing cities. Dual protection—sealed upper plus insulation—for rain-to-sno…
Handles ~17 rainy days
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Dark
Dark Brown Weather-Ready Chelsea Boots
Dark brown Chelseas with a treated upper and rubber sole for light drizzle. Clean lines keep them looking city-smart, not trail-ready.
Handles ~17 rainy days
Shop on Amazon →Best traction sneakers for Portland in December
ForecastStyle pick
The Ridge Chunky Trail Sneaker in Grey
A rugged, comfortable sneaker built for light trails and city streets alike. The chunky sole provides all-day support and a modern, athle…
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ForecastStyle pick
Grey trail running shoes
Waterproof trail runners in grey with a grippy lug sole and reinforced toe. Good for light hiking and off-road runs.
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ForecastStyle pick
Black Packable Waterproof Travel Sneakers
Black waterproof travel sneakers with a lightweight, compressible upper for one-bag trips. Quick-dry lining and grippy sole handle surpri…
Shop on Amazon →Best packable rain shoes for Portland in December
ForecastStyle pick
Grey Road-Ready Walking Sneakers
Cool grey road-ready walkers with balanced cushion—not chunky trail, not dress flat. Designed for flat pavement, metro stairs, and long a…
Handles ~17 rainy days
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ForecastStyle pick
Olive Water-Resistant Packable Trail Sneakers
Olive water-resistant trail-to-city sneakers with a light pack weight. Subtle traction for wet plazas without heavy hiking bulk.
Handles ~17 rainy days
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ForecastStyle pick
White Quick-Dry Waterproof City Sneakers
White waterproof city sneakers that rinse clean after wet streets. Packable silhouette with cushioned midsoles for airports and rainy sig…
Handles ~17 rainy days
Shop on Amazon →Wear them with these outfits
Climate-matched looks for Portland in December.
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FAQ
Are waterproof shoes necessary in Portland in December?
Yes — with roughly 17 rainy days in the month, waterproof or water-resistant shoes are a strong bet.
Do I need boots in Portland in December?
A light boot is worth it for evenings, when temps drop to about 37°F. A sturdy sneaker also works.
Can I wear sandals in Portland in December?
Not really — highs around 46°F are too cool for open shoes on most days.
Can I get by with one pair of shoes in Portland 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 Portland?
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 Portland?
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 Portland?
Yes — hills reward cushion and traction. Prioritize walking shoes or trail-leaning sneakers over fashion flats.