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Rainproof Outfits

With the recent wet weather and the cloudy days ahead, I’ve been thinking about how best to dress for the rain with a fashionable nod toward fall style. In my mind, wet autumn weather doesn’t mean slacking in style. In fact, I see it as a fashion challenge to look great and stay dry. Plus which, fall has become a very aesthetically pleasing season, and I’d hate to let a bit of rain hamper down all the fun fall looks this time of year has to offer. Here are a few tricks and tips for rainproofing your favorite fall outfits.

Combating a drenched appearance after braving an autumn storm relies on two key elements: Outerwear and boots. Both should be waterproof, with the former being able to accommodate layers and the latter versatile enough to wear with multiple outfits. My go-to footwear for fall and winter are waterproof Chelsea boots by Sam Edelman. They are black, with a pull-on silhouette, and have enough tread to brave the elements, but aren’t overly chunky to deter me from wearing them at work or slightly formal occasions. Jacket-wise, I recommend going for a hooded, waterproof garment in olive green. Something with a bit of utility-type style. Olive or military green can go with other neutrals like beige, navy, grey, and black, as well as vivid fall shades of red, orange, and magenta. I picked up a forest green hooded trench-style coat from Costco a few years ago that does a great job of keeping me dry.

What I find convenient about my waterproof black boots and Costco coat is that they can be thrown on most fall-themed outfits without taking away any autumnal aesthetic. This shoe-jacket combo works seamlessly with jeans and a flannel. It also complements a sweater, skirt, and tights look or a turtleneck and trousers outfit. Most outdoor-based brands like L.L. Bean, Carhartt, and Landsend will have quality waterproof options for outerwear, but so do stores like Kohls and Target. As for boots, if you’re in the market for shoes that will get you through many years of fall and winter, check out Sorel. Rocket Dog over on DSW.com also features reliable waterproof boots at a more accessible price point.

A military-style hooded jacket and Chelsea waterproof boots are not the only footwear-outerwear combo that can see your fall outfits through a rainy season. For more rugged looks, consider a rain-resistant parka and hiking boots. This pairing has more of a weekend-warrior vibe, perfect for hiking, visits to the pumpkin patch, as well as brewery tours, flea markets, and most outside fall-related activities. I like the brightly color-blocked offerings from Patagonia for jackets and the cool-toned Merrell Mid Waterproof hiking boot. I can see these as statement pieces with a base of a thermal Henley and cargo pants. Or contrasting with black denim and a striped t-shirt for a graphic fall look. Old Navy’s Packable Oversized Water-Resistant Quilted Jacket comes in dusty rose, cerignola, and blue dusk for a fall version of pastels. This jacket and classic duck boots, when worn with patterned leggings and an oversized sweater, are a chief’s kiss of an autumn-loving look while keeping you dry.

For a more polished take on a rainy fall day, consider pairing knee-high boots with a chic (and water-resistant) trench. This is an obvious approach for office wear and evenings out. A plaid shirtdress with block-heeled knee boots and a standard camel trench gives workwear a bit of fall flair. While a cozy sweater dress with over-the-knee boots and a leatherette trench-style coat gives off both an edgy yet snuggly sense to autumnal style. If you want to play around with the expected aesthetic of tall boots and a trench, wear them with an athleisure-inspired outfit of leggings and a hoodie. Or skinny jeans, a long-sleeved tee, a scarf, and a baseball hat. DSW and Nordstrom are great sources for knee-high boots, with the latter and its outlet store Nordstrom Rack offering up a ton of trench coats at a variety of price points.

In addition to water-resistant outerwear and boots, the third (and often overlooked) piece to a successful rainy-day fall look is waterproof makeup! MAC, Estee Lauder, Lancome, Bobbi Brown, and Maybelline all have waterproof products, including foundation, eyeliner, brow gel, and of course, mascara. Now, if you don’t regularly wear makeup, a stormy day in October is not the best time to start. But for veteran makeup applicators, having a few waterproof products on hand as cosmetic pinch-hitters for those foul weather days will keep you from arriving at your destination looking as if you’ve been crying.

Hopefully, this fall will be full of bright, sunshine-filled days with crisp mornings and cozy evenings. However, if the storm clouds burst, you’ll have a jacket and boot combo ready to keep you and your fall style dry.