Best shoes
9 best shoes for Chicago in January
highs of 32°F, lows of 17°F, 11 rainy days — here's what to put on your feet.
Why these shoes for Chicago in January
Chicago in January averages highs around 32°F, lows near 17°F, 11 rainy days.
Chicago wind and long lakefront walks demand stable soles; winters need real insulation. Expect long walking days in Chicago: 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 insulated boots, thermal sneakers, wool-lined 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 insulated boots for Chicago in January
Cognac
Cognac Shearling-Lined Ankle Boots
Cognac ankle boots with plush shearling lining for dry cold and light snow. Warm without the bulk of full winter boots—ideal for short ci…
Warm when lows drop
Shop on Amazon →
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…
Warm when lows drop
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Espresso
Espresso Shearling Pull-On Winter Booties
Espresso shearling pull-on booties that slide on for early trains and cold markets. Cozy lining with a rubber sole for light snow and ice…
Warm when lows drop
Shop on Amazon →Best thermal sneakers for Chicago in January
Charcoal
Charcoal Insulated Knit Winter Sneakers
Charcoal knit winter sneakers with insulation for freezing mornings and airport runs. Sneaker silhouette with cold-weather warmth for urb…
Warm when lows drop
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ForecastStyle pick
Cozy Shearling-Lined Suede Clogs
These suede clogs feature a plush shearling lining and a supportive cork footbed for maximum comfort. An ideal slip-on for errands or lou…
Warm when lows drop
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Evergreen
Evergreen Shearling-Lined Suede Clogs
A molded cork footbed and plush shearling lining provide all-day comfort for errands or relaxing at home. The durable rubber sole offers …
Warm when lows drop
Shop on Amazon →Best wool-lined shoes for Chicago in January
ForecastStyle pick
Black Shearling-Lined Lug-Sole Boots
A rugged lug sole provides all-day traction while the plush shearling lining keeps feet warm and comfortable. The perfect everyday boot f…
Warm when lows drop
Shop on Amazon →
Taupe
Taupe Wool-Lined Leather Ankle Boots
Taupe leather ankle boots with a wool-blend lining for shoulder-season cold. Neutral color and modest heel height for all-day walking in …
Warm when lows drop
Shop on Amazon →
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 …
Warm when lows drop
Shop on Amazon →Wear them with these outfits
Climate-matched looks for Chicago in January.
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FAQ
Are waterproof shoes necessary in Chicago in January?
Yes — with roughly 11 rainy days in the month, waterproof or water-resistant shoes are a strong bet.
Do I need boots in Chicago in January?
Yes — average lows near 17°F mean insulated boots will keep your feet from freezing on the walk back to the hotel.
Can I wear sandals in Chicago in January?
Not really — highs around 32°F are too cool for open shoes on most days.
Can I get by with one pair of shoes in Chicago in January?
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 Chicago?
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 Chicago?
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.