Ask Allie: Casual Winter Footwear

I work in a casual office–and I mean CASUAL–but I feel my shoe wardrobe is lacking. Do you have any recommendations for casual shoes that aren't sneakers but would keep my tootsies warm in the Chicago winter?

I do believe that sneakers should be left for athletic activities, but that doesn’t mean you have to dress up or sacrifice style. I used to work at an office where yoga pants, UGG boots, and flip flops were the standard, so I understand how you may not feel comfortable in pumps or even ballet flats. Here’s three casual shoe styles I adore that are comfortable, stylish, and perfect for cold Chicago winters!

how to style tennis shoes

Unlike a sneaker which is chock-full of high-tech materials and cushioning to improve your game, a tennis-style shoe is far simpler. Usually of canvas with a rubber sole, this is a classic style that has come back en vogue and looks fabulous with everything from jeans to sundresses. This winter, wear with cozy socks and your casual pants, come spring pair with skimmers and full cotton skirts.

casual shoes boots how to style

Boots are the type of footwear that just get better with time. Salt, snow, dirt… these just improve the character of many styles of boots. Brown boots weather best, especially if they are a riding, engineer, or Western style. Black boots in styles known to be worn a lot (engineer, riding, work/Doc Marten) also carry off the distressed look. A pair of pull-on style is easy polish for a wardrobe of slim jeans and casual tops and can be polished to wear with more casual dresses and tights. I find most weekends I am in a knit top, sweater, stretchy jeans and tall boots because it’s not only easy and comfortable, but looks polished and put together.

how to style oxfords brogues

This is another comfortable shoe style that has come back en vogue and makes casual yet polished dressing easy. They can be worn pretty much the same way as tennis shoes but the plus to oxfords is that they beg to have your socks on display. A simple tee shirt and jeans are given a level of cool with some nubuck oxfords and pastel-striped socks, or polka-dot brogues paired with hot pink socks with skulls on them. Oxfords also look great with cropped pants and skirts (see my post on how to style brogues here), and are a style of shoe that begs for a statement-making color or finish!

While they aren’t oxfords, desert boots has also returned to the fashion scene and look fabulous with jeans and casual pants. The Clarks Desert Boot is a classic, but there’s a lot of alternatives in fun colors and with wedge heels and other unique details.

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1 Comment

  1. Sonia
    February 25, 2013 / 1:46 pm

    I agree with your assessment 100% that sneakers are not for office wear. Despite, working in an ultra-casual office environment with jeans as the preferred attire, I wear tennis shoes and have about eight pair of them in different styles and colors. My favorite are my red Converse ones (aka Chuck Taylor’s) in canvas with leather on the sides. Always get compliments when I wear them.

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