Best shoes
9 best shoes for New York in May
highs of 71°F, lows of 54°F, 11 rainy days — here's what to put on your feet.
Why these shoes for New York in May
New York in May averages highs around 71°F, lows near 54°F, 11 rainy days.
New York is a pure walking city — subway stairs and long blocks punish weak cushioning. Expect long walking days in New York: flat pavement is kind to most walking shoes.
Plan on two pairs — one built for the weather extremes and a lighter backup for evenings and dry stretches.
Our picks focus on everyday sneakers, light boots, walking 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 everyday sneakers for New York in May
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…
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ForecastStyle pick
Black-and-White Retro Everyday Sneakers
Black-and-white retro court sneakers with a timeless silhouette. Cushioned enough for walking days, stylish enough for street photos.
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ForecastStyle pick
Grey Summit Chunky Trail Sneakers
A rugged sole provides superior traction on and off the trail, while the cushioned interior ensures all-day comfort. The chunky silhouett…
Shop on Amazon →Best light boots for New York in May
ForecastStyle pick
Classic Black Leather Chelsea Boots
Timeless black leather Chelsea boots with elastic side gussets and a walkable stacked heel. A capsule staple for city evenings and cool s…
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ForecastStyle pick
Black ankle boots
Classic block-heel ankle boots in black. Goes with jeans, midi skirts, or straight trousers — an autumn and winter staple.
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ForecastStyle pick
Black Shearling-Lined Chelsea Boots
Black Chelsea boots lined with soft shearling for cold city evenings. Sleek shaft and walkable sole keep them polished for dinners after …
Shop on Amazon →Best walking shoes for New York in May
ForecastStyle pick
The Summit Chunky Trail Sneaker in Gray
A rugged sole provides all-day comfort and traction for city adventures or light trails. The versatile gray color and streamlined silhoue…
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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.
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ForecastStyle pick
Black Waterproof Knit High-Top Sneakers
Black waterproof knit high-tops that slip through security easily and dry faster than leather after a downpour. Cushioned midsoles suppor…
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Climate-matched looks for New York in May.
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FAQ
Are waterproof shoes necessary in New York in May?
Yes — with roughly 11 rainy days in the month, waterproof or water-resistant shoes are a strong bet.
Do I need boots in New York in May?
Not really — average lows near 54°F stay above the boot threshold. A supportive sneaker is enough.
Can I wear sandals in New York in May?
Yes, for midday. Highs around 71°F are on the edge, so plan a backup for cooler mornings and evenings.
Can I get by with one pair of shoes in New York in May?
Many travelers do fine with one strong walking pair. Add a second only if you need dress shoes or a wet-weather dedicated option.
What about dressy dinners in New York?
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 New York?
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.