How to Stay Fashionable in Comfort Footwear

How to Stay Fashionable in Comfort Footwear

You want to look your best, whether you’re lounging around the house or stepping out into the shopping district to find a brand-new outfit for work. You also want to feel comfortable, relaxed, and able to move around freely while you do it – that’s where comfort footwear comes in.

What do you picture when you think of comfort wear?

Do you envision drab, boring flats, and snooze-ville sneakers?

If so, you should know that dressed-down doesn’t necessarily mean dowdy.

New technologies and forward-thinking designers have managed to meld both style and comfort together in new and fashionable ways. If you’re struggling to make the connection, this guide will help you break down the basics so you can look your best and find the most comfortable shoes for your lifestyle.

Related: What are the most comfortable shoes for men and women?

You Don’t Need to Sacrifice Comfort for Quality

It’s easy to slip into the idea that comfort = low-quality, but surprisingly, the opposite is typically true. Bargain basement sneakers, sandals, and flats might seem to look similar to more expensive brands, but their low price point comes with a sacrifice in material quality.

Loose stitching, low-quality suede, and cheap rubber soles won’t necessarily make themselves obvious at first, but after you wear them for a time, your brand-new shoes may start to look a bit like you’ve been wearing them for five or more years.

Instead, shop for relaxed footwear from a reliable brand that’s time-tested and respected, like Birkenstock. Their Suri 273 is an excellent example of style and comfort melted into one, especially for warmer weather. The durable suede leather upper comes in a variety of shades to suit your changing mood, while the flexible and long-lasting soles cradle your foot in luxurious comfort. Best of all, they’re multi-talented; pair them with a dress for brunch or a pantsuit for business.

Activewear? Not Just for Active Living!

Hate dress shoes? Here’s the good news: you can fill their role with the right activewear for your feet, thanks to modern and classy new designs. The once-lowly sneaker and outdoor tennis shoe is no longer a denizen of only the court; instead, designers are starting to recognize their comfort for what it should be – a regular player.

Classy white or black oxford-style sneakers look just as suitable under suit trousers as they do at the gym. Double monks are nearly indistinguishable from dress shoes when crafted in fine Italian leather, but inside, it’s all comfort, all day long.

Need something street-smart with urban appeal? Activewear designers have your back. Check out these beautiful tan Chennai shoes by Finn Comfort for women. For men, Ecco’s Bison Cow Leather Chukka boot is hard to beat.

Rock Wedges Or Chunky Heels, Not Stilettos

Any woman who has worn stilettos for an entire day – especially if you happen to be on your feet for most of the day – knows the after-effects all too well. Stilettos may be beautiful, but they aren’t exactly comfortable to wear, and over-wearing them could even cause repetitive strain injuries in the lower legs and back. If you’re already lamenting the loss of your favorite sensual shoe, don’t despair just yet: there’s a way to get the best of both worlds without giving up.

Wedges, kitten heels, and chunky heels all have one thing in common: they distribute pressure around the heel more evenly. What that means for you, dear shoe lover, is better stability and fewer aches after a long day. Just like sneakers, they, too, now come in enough styles to suit a variety of situations including business and casual outings.

Some, like Jillie by Munroe, are fancy enough for even the most high-end party when paired with a sleek matte black or red dress. Others, like Mara by Munroe, are a little bit more demure, pairing well with dresses and dress pants alike. Others are more whimsical in design with polka dots, checkered upper soles, or shimmery suede. Whichever you choose, look for a wide, stable heel for maximum comfort or a thinner, kitten-style heel for more sensuality and style.

Match The Right Shoe with the Right Outfit

Last, but not least, is the importance of matching the right comfort shoe with the right outfit. You, fashion-lover, are a modern footwear cupid, and your decisions can make or break your sense of style. But have no fear: a few basic shoe-matching guidelines and a bit of fashion mojo are all you need to make the best matches.


Wearing jeans? You have the most flexibility. A stylish sneaker or tennis shoe works best for casual dates and afternoons downtown. Step the look up with a casual low-upper boot or leather loafers. A casual ankle boot with cutouts adds sensuality for women, while rich Italian leather uppers in black or navy blue dress them up for men.


Dresses are a bit more complex. In the summer, pair light-colored dresses with comfort wedges featuring natural elements like twine, cork, or wood. In the fall, warmer fall and winter dresses pair better with boot-style wedge heels. Not into heels? This is the perfect time to mix in simple and sublime flats like this Aline shoe by Beautifeel. They’re a dead ringer for fancier shoes, but with an absolutely divine, out-of-this world soft interior.


Wearing a suit to a business meeting, or meeting clients for tea? Skip anything loud or sensational and stick with time-honored basics like low-heeled pumps, oxfords and loafers. All three of these options carry a casual, friendly and approachable look without making you appear stiff, cold, or rigid, and oxfords are an essential for any man’s closet.

Color Matching Matters, Too

Shade, color, and texture-wise, you have a few options depending on the outfit you wear. Always strive to match the color(s) in your shoes to either the most dominant color in your outfit or a less dominant, but still obvious color instead.

Here’s an example: you’re wearing dark blue jeans, a white tee-shirt, and a black leather jacket. Pairing this outfit with dark navy blue loafers might seem like an okay choice (and it really is), but it’s not really anything special. Switch out the navy blue loafers for either white or black instead and you’ll create contrast that draws the eye up and down your body.

An example in the other direction: You’re wearing a basic business suit in black, but you’ve grabbed a fairly bright red pair of leather loafers to go along with it. The only way this might work is if you’re wearing a red dress shirt under your jacket, but typically, bold colors paired with basics will compete with your look. Try a darker brick red, or go for a black lace-up wingtip with red laces.

It’s important to be cautious with shade, too; aim for the closest match between your outfit and your shoes. Avoid pairing off-colors, like pinkish-red or off-white, with bold-colored clothing in fire engine red or crisp snow white. The match won’t look quite right and will depreciate your look. If all else fails, go to a simple and timeless favorite – black. It matches nearly everything and won’t let you down.

With just a few basic footwear fashion guidelines, it’s easy to put your own creative spin on comfort footwear. Dressed for success in your Sunday best or just relaxing around the house, looking your best will make you feel your best, too.


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