One very rainy winter day, I met stylists Paula O’Neil and Tracy Pendergast at a coffee shop in downtown Portland, Ore. I put a little more thought than usual into my outfit that morning, but ultimately decided on comfort: waterproof Sorel boots, pants that dry quickly, a sweater and my waterproof coat. Style would have to wait. Function was more important.
When I arrived at the coffee shop, feeling a bit like a drowned rat, I looked at Paula and Tracy who were impeccably styled despite the weather. I thought: “Wow. They manage to actually look really put-together. How is that possible?” So I asked them: How can you dress for the weather and dress with style? Apparently, it can be done.
Here are a few basic rules for dressing with style in the winter, courtesy of O’Neil and Pendergast, co-founders of Est Ovest Style.
Rule #1: Don’t take your performance wear to the streets. Leave your ski coat for the slopes, your workout wear for the gym. Compartmentalize your clothing and outerwear.
Related: 10 Winter Coat Styles to Cozy Up In
Rule #2: Layers. Layers — including camisoles, button-down shirts, sweaters, scarves, tights and the like — will keep you the right temperature inside and out, and can help you have great personal style. (But remember, fit and proportion are hugely important, especially with layering.)
Rule #3: Add some color, even just a pop of color in an accessory like a scarf or a hat. When it’s dark and cold and wet, the last thing you want is to be dressed head-to-toe in shades of black and gray.
Rule #4: Accessorize. Coco Chanel is known for saying something like “Before you leave the house, take one thing off.” That’s often true, but in the winter, it can be helpful to add one thing — maybe one stylish accessory.
Rule #5: Incorporate one trend with your style. Take a runway idea and bring it down a notch and make it work for you with your lifestyle.
Related: Fierce Fashion: Wearing Animal Print in Style
All good rules, but I still thought: “But it’s rainy and cold! My boots are so warm and keep me dry! I don’t want wet feet. And if I wear a hat, I’m going to have hat head.”
Here are a few more tips.
Shoes: There are a lot of good all-weather options for footwear and outerwear, Pendergast says. La Canadienne and Aquatalia make great all-weather shoes and boots that also have style, terrific if you’re going to be out running errands or walking around in the elements. Sorel has also come a long way with style in the last couple of years. Another option, she adds, is the “Mr. Rogers approach”: Wear your boots to work, then put on a pair of heels when you get to work. And finally, weatherproof your shoes. When we met, both O’Neil and Pendergast were wearing suede boots — in the downpour. My suede boots 
are in the closet, not to be seen ‘til the weather breaks. Weatherproof them, and you can wear them all winter, they say.
Related: How to Save Your Soles this Winter
Coats: A classic trench coat with a zip-in lining for winter will get you through most of the winter in much of the U.S., O’Neil says. It’ll keep you dry and warm, and it defines your waist, giving you an hourglass figure rather than a marshmallow figure, she says. Ski coats are great for skiing, but not so much for looking great on the street, she adds.
Hats: Get a great styled hat, Pendergast says. You don’t have to wear a ski hat (see aforementioned comment about compartmentalizing). Milliners can make a fantastic hat that will leave you without hat head. Plus, they give you style and color.
Layering: The keys are color, style and proportion, keeping a waist, O’Neil says (see aforementioned note about marshmallow shape). Don’t layer with big bulky sweaters, she says, but gravitate to thin but warm layers — like cashmere sweaters and cute t-shirts. Wear dresses with tights.
Related: Learning to Layer
Color and accessories: Can be one and the same, or not. Wear a little pop of color: Black and gray don’t lift you, Pendergast says. Incorporate spring pieces as part of your layering during the winter. Tangerine is the “in” color for spring, so why not add in a tangerine scarf with your basic black cashmere sweater? Yellow is also big for spring. Put on some yellow shoes. Or try a great red hat, a yin-yang cuff bracelet or a chunky turquoise necklace or earrings. “Accessories are what take you from ‘clothed’ to ‘dressed,’” Pendergast says.
“Cute and comfy or practical are not mutually exclusive,” she says. “Have fun with it,” O’Neil adds. You’ll look and feel better. Definitely needed for these dark, cold, wet months of winter.
With these tips in mind, hopefully I'll look a little more stylish the next time I brave the winter weather.
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Est Ovest Style mavens Paula Brady O’Neil and Tracy Gaillard Pendergast believe in the Italian style philosophy: that one’s closet should only have items in it that make the wearer feel equal parts attractive, confident, and comfortable. Est Ovest Style believes that fewer items worn well is better than many items worn poorly, that fashion should never be too difficult, and most importantly that style is not a privilege for some, but a right for all.
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