5 Men’s Versatile Waterproof Boots to Shop for Fall

April showers may be long past, but that doesn’t mean rainy days aren’t ahead for fall. While many men ignore the weather report and find themselves puddle jumping in their dress shoes or sneakers, there’s a practical alternative — waterproof boots that can do double duty as casuals.

From chukkas to hikers, these styles are not only waterproof, but incorporate a range of comfort features. Footbeds are done with plenty of cushioning, while some incorporate proprietary technologies for enhanced breathability. For those living in climates with excessive rain, Hunter has some fun with a classic Chelsea style that can stand up to just about any downpour.

Here, FN has rounded up some waterproof picks from Sorel, Timberland and more to help you navigate a rainy day.


1. Sorel Madson Chukka

This classic silhouette is made extra comfortable and durable with an Ortholite cushioned footbed and rubber outsole.

SOREL Madson Chukka Waterproof
Sorel Madson waterproof chukka.
CREDIT: Courtesy of Zappos

2. Florsheim Midtown Chukka Boot

Stay looking polished even in a downpour with this rain-ready ankle boot featuring a moisture-wicking lining and removable cushioned footbed.

Florsheim Midtown Waterproof Chukka Boot
CREDIT: Courtesy of Zappos

3. Timberland Flyroam Trail Fabric

A lightweight hiker moves from city streets to mountain trails, incorporating leather and Cordura fabric with a TimberDry waterproof membrane and Ortholite cushioned footbed. Eco-friendly outsoles are made of recycled rubber.

Timberland Flyroam Trail Fabric Waterproof
CREDIT: Courtesy of Zappos

4. Geox Mattias ABX 22

The Italian brand incorporates its proprietary Respira perforated sole for breathability underfoot, while its Amphibiox waterproofing keeps feet dry.

Geox Mattias ABX 22 Waterproof Boot
CREDIT: Courtesy of Nordstrom

5. Hunter Originals Exploded Logo Chelsea

This iconic pull-on style in rubber stands up to any downpour, with interior comfort enhanced with a quick-dry lining and cushioned footbed.

Hunter Originals Exploded Logo Chelsea Boot
CREDIT: Courtesy of Nordstrom

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