Best shoes
9 best shoes for Pittsburgh in May
highs of 70°F, lows of 49°F, 15 rainy days — here's what to put on your feet.
Why these shoes for Pittsburgh in May
Pittsburgh in May averages highs around 70°F, lows near 49°F, 15 rainy days.
Waterproofing is the deciding factor — expect wet sidewalks and occasional downpours, so anything porous is going to soak through by lunch.
Plan on two pairs — one built for the weather extremes and a lighter backup for evenings and dry stretches.
Our picks focus on packable rain shoes, 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 packable rain shoes for Pittsburgh in May
Charcoal
Charcoal Wide-Fit Walking Shoes
Charcoal wide-fit walking shoes for swollen travel feet and full days on hard floors. Stable sole and soft lining for comfort over style …
Handles ~15 rainy days
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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…
Handles ~15 rainy days
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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 ~15 rainy days
Shop on Amazon →Best light boots for Pittsburgh in May
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…
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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 …
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Taupe
Taupe Waterproof Lug-Sole Ankle Boots
Neutral taupe waterproof ankle boots with a refined lug sole for grip on slick stone without aggressive trail styling. A travel wardrobe …
Shop on Amazon →Best walking shoes for Pittsburgh in May
ForecastStyle pick
Classic White Low-Top Everyday Sneakers
Crisp white low-top sneakers with a clean court silhouette for everyday travel. Easy to style with jeans, skirts, or joggers and light en…
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ForecastStyle pick
White Salomon Trail Sneakers
These technical sneakers provide excellent grip and support for light hikes or city errands. The streamlined design offers all-day comfor…
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Ivory
Ivory Minimal Walking Sneakers
Ivory minimal walking sneakers with a quiet sole and slim profile. Easy to style for city photos without looking like running gear.
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FAQ
Are waterproof shoes necessary in Pittsburgh in May?
Yes — with roughly 15 rainy days in the month, waterproof or water-resistant shoes are a strong bet.
Do I need boots in Pittsburgh in May?
A light boot is worth it for evenings, when temps drop to about 49°F. A sturdy sneaker also works.
Can I wear sandals in Pittsburgh in May?
Yes, for midday. Highs around 70°F are on the edge, so plan a backup for cooler mornings and evenings.
Can I get by with one pair of shoes in Pittsburgh 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 Pittsburgh?
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 Pittsburgh?
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.