I must admit, the lifestyle of a professional freelancer has its perks.

If you’ve ever read my book, you know that I’m a pretty big fan of wearing sweatpants. As I’ve said before, sweatpants are the new business casual of the virtual economy. However, as I’ve recently learned, an overly casual wardrobe can come back to bite you. This is particularly true with regard to what you wear on your feet.

In this article, I’ll briefly describe why I’ve started wearing shoes – even though I never leave my house.

Socks are Awesome, But…

Having worked in the “real world” for several years after college, I always looked forward to casual Fridays. In addition to jeans, which were the common wardrobe for that day of the week, it also meant that I got to wear more comfortable shoes. Dress shoes can really be a pain (literally). So, it’s no surprise that after I started my freelancing business, I was particularly excited about not having to wear any shoes while working.

This approach worked well for a few years, but as I’ve gotten into my thirties, I’ve started to feel the bodily effects of my athletic career (I played high school and college baseball). This is particularly true in the soles of my feet. I’ll spare you a lot of details (discussions about feet make me nervous too), but suffice to say that walking around flat-footed on tile and carpet all day is not the most ergonomic solution.

In addition, during the winter months, the cold temperature can really catch up with you.

House Slippers Anyone?

To solve this problem, my first approach was to buy a pair of house slippers. No, I’m not talking about the ones that your grandpa wears. I actually did quite a bit of research and tried to find some that looked like real shoes (pictured below – you’ll see a pair that resembles the ones that I had). Unfortunately, even house slippers provide little support to your arches, especially after several months of use. The soles are just not meant to be worn ten hours a day, five days a week.

Why I Started Wearing Shoes Again

So, despite my initial reluctance, I thought it best to start wearing shoes again. I mean, let’s face it – it was either that or cold feet and sore soles.

To find a happy medium, I decided to buy some really nice athletic shoes – see below – which also happen to look great with sweatpants. Make sure you find some that have sturdy soles, especially if you stand during meetings (like I do).

Do You Need Freelancer Shoes?

What about you? What type of footwear do you prefer as a professional freelancer? Leave a comment below!

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Matt Keener is the original "Executive in Sweatpants," having built a successful online consulting business (from home). His best-selling book offers tips for capitalizing on outsourcing and freelancing. Matt holds an MBA and has been featured by many recognizable brands, including Upwork (formerly oDesk), Elance, Insightly, the Dave Ramsey Show, and Entrepreneur.com.

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