If you live anywhere close to our hometown of Boston, you’ve spent the past few weeks sloshing around in cold, wet conditions. This time of year, rugged winter boots are our best friends – but what about when you need to look your best for a winter wedding or morning presentation? We build waterproof dress shoes for days like these – everything from classic oxfords to refined chukkas. Read on for our favorite waterproof dress picks to get you through the season in comfort and style.
Pictured: DresSports Waterproof Cap Toe ($150)
Head to that important Monday meeting, even on the wettest of days, in the DresSports Waterproof Cap Toe. The modern silhouette, handcrafted in premium leathers, will keep you looking sharp, while the waterproof construction will keep your feet warm and dry. Meanwhile, ETC® linings provide breathability and moisture wicking for maximum comfort – from the cold commute to your warm office. In black and tan, these classics will become your new winter companions.
Pictured: Essential Details Waterproof Wingtip ($110)
From the workplace to your next wedding, the Essential Details Waterproof Wingtip is a winter weather marriage between fashion and function. The Hydro-Shield® construction offers waterproof leather, a seam sealed, waterproof insole, and a gusseted tongue to help keep feet dry wherever the day takes you. An EVA footbed conforms to the shape of your foot for a personalized fit, while the rubber outsole offers traction and reduces foot and leg fatigue. These secret weapon wingtips will surely be at the front of your wardrobe this winter (and beyond).
Pictured: Essential Details II Bike Toe Slip-On ($110)
If the ease of a slip-on is something you’re after, the Essential Details II Bike Toe Slip-On is for you. Featuring a more tailored fit, these slip-ons offer waterproof leathers and slip-resistant outsoles for wet conditions. The cushioned, EVA footbed and supportive heel cup will keep you comfortable from your morning coffee run to evening dinner plans. Wear these with everything from your everyday suit to your favorite pair of jeans. These slip-ons are sure to be in heavy rotation this season.
Pictured: DresSports Modern Waterproof Chukka ($170)
Give wet weather the boot with our DresSports Modern Waterproof Chukka. These boots mean business with waterproof leathers, a higher vamp for more coverage and a durable VIBRAM outsole for traction in tricky weather. Strobel construction gives forefoot flexibility while truTech® offers lightweight shock absorption to keep you comfortable all day long. A bonus removable Ortholite® footbed with EVA heel cup provides lightweight breathability and durability for long wear cushioning. Wear them with cuffed denim or dress them up with slacks – these versatile, waterproof chukkas will be your winter weather cure-all.
Check out more styles from our waterproof dress collection.