Ask yourself these questions when trying on stylish comfortable shoes

Mary Sue Papale
3 min readMay 28, 2020

I’ve been in the shoe business my whole career (more than 30 years!). Over this time, I have learned a lot about shoes. One of the thing I know for sure is what to look for when trying on stylish, comfortable shoes. I have put together this guide.

Buying a new pair of shoes is always exciting. If you want to make the most of your investment, don’t lean too heavily on price. Since stylish walking shoes are engineered differently, it only makes sense they’ll cost a little more.

One thing that is crucial is fit. If the shoe doesn’t feel right, then it’s not worth spending money on. Remember to try on and review all aspects of the shoe so you know exactly what you (and your feet) are getting into.

Whether you’re trying on your first or fifteenth pair, here’s a quick checklist of questions to keep in mind.

How does the size feel?

When shopping, choosing a size or style that fits right just makes sense. Bear in mind that sizing is only a guide, and how you feel in the shoe matters most. You may be wary to ask for a different size just because it seems weird, but sizing varies between brands. Resist buying shoes that aren’t comfortable, especially with advancements and innovations that make finding stylish, comfortable shoes so much easier.

When did you try them on?

Those stylish, walking shoes may not be so comfy after all.

Did you know that the time of day you try on shoes makes a significant difference? Your feet naturally swell up post-work or after walking long distances. They’ll almost always be too tight at this time, so keep in mind they’ll feel different in the morning. With online shoe purchases, try them on at different times to double-check the comfort level. Return or exchange the shoes within the return window if need be.

Are you wearing socks?

Each time you try on new shoes, we recommend bringing a pair of your usual socks. This is especially true for sneakers and boots, but can be important for any pair. Not only does it feel more natural, but you’ll also find a more accurate fit.

Did you walk in them?

Once you find a pair of stylish walking shoes that strike your fancy, take a stroll around the store. For online purchases, wear them around the house. This will give you a better idea of how tight (or loose) they are, whether there’s enough room in the toes, and if it feels natural.

How’s the sole?

The type of sole will significantly affect your comfort level. After all, its chief purpose is to be a cushion against unhealthy impact and unnecessary pressure.

One way to check if the sole is shock absorbent and durable is by jumping a bit while wearing the shoes. Then, check how your heels, ankles, and legs feel afterward. A comfortable sole should absorb most of the stress and prevent pain. Try walking on different surfaces like carpets, tiles, and cement as well. All this might seem tedious, but at least you have a clear idea of whether those stylish walking shoes are worth the investment.

To learn more about stylish, comfortable shoes, check out my complete guide here.

If you are interested in learning about how to shop for stylish, comfortable shoes, click or Shop Suggies

BENDY by Ashbury Skies

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Mary Sue Papale

I am co-founder of Bendy by Ashbury Skies. The BENDY is a stylish, comfortable shoe with a lower carbon footprint, ethically made California.