How to Choose Shoes That Feel as Great as They Look

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Ask any woman about her fashion woes, and chances are “shoes” will be somewhere near the top of her list. We all love a great-looking pair of shoes, but the trouble is that as we get older, it becomes harder and harder to find footwear that lets us express our style and keeps our feet comfortable. This disconnect breeds a tremendous amount of anxiety and dread for many women. Then, in a vicious cycle, we find ourselves dressing down more often (so we can wear more comfortable shoes—ahem, sneakers—more frequently), which breeds more discontent and makes us feel less confident.

Luckily, you don’t have to maintain a problematic relationship with your footwear. Keep reading for my tips to help you reassess your current shoe collection and find footwear that works for you.

First, get rid of your outdated shoes or anything that no longer fits you well. If your shoes are out of style, the rest of your outfit—no matter how well curated—will look “off” as well. So, go through your closet and pull out any shoes with the wrong heel or toe shape, or any pairs that have outdated features, and donate them today. Do the same with footwear that no longer fits you the same way it once did. Remember, your feet change over time, and the shoes that once felt good may no longer work for you. But never fear, you can get rid of footwear that no longer suits your life and devote the extra room in your closet to a new pair of modern and fabulous shoes.

Toss your worn-out footwear too. Many closets are full of shoes that have seen much better days. Don’t waste closet space on your well-worn and well-loved shoes that are now falling apart. No matter how comfortable they may be, they no longer serve you today if they look too shabby to wear out in public. Toss them out and make room for more.

Next, commit to wearing nice shoes—even when you don’t have to! If you aren’t used to wearing dressier shoes (and the nice outfits that go with them) on a regular basis, even the most well-built footwear can feel uncomfortable. So even if it’s challenging at first, start forcing yourself to wear nicer shoes on most days. It’s so easy to throw on a pair of sneakers without a second thought, but that’s not doing yourself any favors in the style department. However, when you consistently wear your nicer ballet flats, sandals, wedges, and (sometimes) heels, you will look better, feel better, and soon you’ll even adjust to wearing shoes you once avoided.

When in doubt, wear a flat. If you’re not sure you can survive your busy day in heels, opt for a dressy ballet flat or sandal. These options will still give your outfit a dressy feel without stressing your arch and ankles in a heel. If you feel you need extra support, go with a flat Mary Jane style.

Look for little (unexpected) embellishments. Face it—you likely won’t be walking around in stilettos on most days, because very few people can wear them for long periods of time. But that doesn’t mean you can’t still look and feel great in your dressier footwear. Cute or even sexy shoes don’t have to be uncomfortable, after all. A pair of cushioned and supportive sandals can still be beautiful—especially if they have a metallic finish or an interesting detail on the ankle strap. Cute and colorful ballet flats will keep your toes happy all day when they have a soft elastic topline gently hugging your foot. Texture also adds plenty of interest; a comfortable pump with a 2-inch heel in patent leather, alligator, or snakeskin will steal the scene just as well as a sky-high stiletto would—plus with a more reasonable heel height, you won’t run the risk of spraining an ankle!   

Spend your money on higher-quality shoes. You could buy forty pairs of cheap shoes that hurt and don’t look that great, or you could buy fewer pairs of high-quality, beautiful shoes that feel comfortable and work well with a variety of outfits. Don’t be afraid to invest your money in more expensive footwear. You get only two feet to carry you through your entire life, so it’s better for you in the long run to opt for well-made shoes. To start out, find a high-quality pair of beige and black shoes that can be paired with lots of options for special occasions. And as a bonus, once you know you’ve got reliable footwear covered, you will likely feel more comfortable wearing your dressier clothing.

 Try, try (and try some more) before you buy. Each woman has her own foot-related issues, whether it’s a high instep, flat feet, wide or narrow feet, or bunions. Any of these may make finding the right pair of shoes more difficult. So when you are shopping, don’t just buy the first pair that fits “okay.” Instead, try on lots of different styles from different manufacturers to see which ones fit you best. Once you have found the perfect pair, you’ll realize they were worth the wait.

 If you must wear “tennis shoes,” get cute ones. Sometimes it’s most convenient and comfortable to wear a fashion sneaker or workout shoe, but that doesn’t mean you can’t find styles that look great. So, when you’re shopping for athletic shoes, avoid any pair that features flashy logos, excessively bright colors, or too many details. Nowadays you can find plenty of fashion sneakers and even workout shoes that look sophisticated and modern. Opt for a streamlined, minimalist shape and you’re guaranteed to look sleek, not sloppy.

Now, read on for a quick inventory of the shoes you should have in your closet and a few ideas for styling them.

Flats. You can’t go wrong with a great pair of flats. They tend to go with everything, they never go out of fashion, and each season they feature new details to keep them feeling fresh and modern. Wear them with everything in your closet.

How to Choose Shoes That Feel as Great as They Look

Sandals. Sandals are the perfect shoe for summer or anytime it’s warm and there’s no chance of rain. Flat sandals go well with most everything, including casual wear and beach attire, and they’re even appropriate in more nontraditional offices. Meanwhile, heeled sandals give off a dressier vibe, perfect for going out to a nice dinner or attending a dressy event like a wedding or cocktail party.

How to Choose Shoes That Feel as Great as They LookHeels. Thankfully, it is possible to find high heel pumps that are both beautiful and comfortable! Stylish and supportive heels may be a little harder to find or slightly more expensive, but they are worth the investment because your feet are important! If you prefer to spend most of your time in flat shoes, save your heels for the special occasions where they will really show off your outfits, like weddings, important business meetings, or parties.

How to Choose Shoes That Feel as Great as They Look 

Wedges. Wedges are beloved by many women because they provide the height of a heel, but unlike heels they keep your feet stable and support your arches. Wear them with any outfit you would normally pair with a heel: dresses, skirts, slacks, and jeans. You’ll enjoy the added height minus the discomfort or balance issues.

How to Choose Shoes That Feel as Great as They Look

Boots. Every woman needs to own a knee-high boot and a pair of ankle boots. Knee-high boots come in handy in colder weather, when you can pair them with jeans or dresses and skirts with fleecy leggings. Meanwhile, an ankle boot or bootie style goes great with leggings or jeans in the fall and winter.

How to Choose Shoes That Feel as Great as They Look

Sneakers. When you have a great pair of sneakers, you can wear them out and about and still look put together. Unless you’re going to the gym, try to stick to wearing fashion sneakers rather than athletic sneakers most of the time. But keep in mind that many athletic sneakers now look every bit as chic as fashion sneakers—so use your best judgment and do what makes you feel great inside and out!

How to Choose Shoes That Feel as Great as They Look

Above all, keep in mind that your relationship with shoes can and should always be evolving. The styles you once loved may no longer resonate with who you are today. Or maybe you’ve realized it’s time to find shoes that allow you to move more comfortably through the world. Either way, you don’t have to settle for boring footwear or worry that your most fashionable days are behind you. There are plenty of great shoes available that look as wonderful as they feel, and these are the shoes that will let the real you shine through.



  • Marla Tomazin, Certified Image Consultant, established her image consulting business in 1990 with the goal of helping clients identify an authentic image and develop its effective expression. Marla utilizes her abilities in evaluating body shape, movement, and coloring as well as synthesizing optimal cuts, lines, colors, and textures. This results in balance and proportion that accentuate attributes and conceal flaws. Marla has appeared on numerous TV and radio stations and programs. Visit

3 Responses

  1. Fran says:

    What about people who need to wear arch support?

  2. Marla Tomazin says:

    I’m sorry, but this is outside my area of expertise.

  3. Ilze Gallant says:

    I always look forward to Marla’s articles because they are interesting to read & very informative.
    Can’t wait for next month…

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