I had a fantastic question come in from our blog Insider that reads like this…

“I enjoy dressing up in dresses and skirts for work but cannot do without my comfortable tennis or walking shoes.  What type of dressy outfit or what style of comfortable shoes do you recommend for those who have a hard time with flats, pumps, and heels?”

Fantastic question, Kim!  I can completely relate.  Comfort is crucial for me too but before you ditch heels all together here’s one thing to keep in mind.

There are certain brands that are at the forefront of melding comfort and style so that you can wear pumps and heels and be comfortable.  Those brands I’ve included on the pinterest board.

Also, do keep in mind that many designer shoes hurt because the measurements were made for a fit-model and not the regular person (frustrating, isn’t it!).  So if you do go with heels measure your foot and measure the shoe – because there’s a good chance that if the shoe fits right, even with a heel, it will be more comfortable.

However, if heels are still out of the questions, you’ll find inspiration for cute shoes that are office approved here.

Allow me to summarize some of your shoe options to wear with dresses that are comfortable, cute and of course flattering:

D’Orsay Heels



D’Orsay heels are very flattering heels because they don’t break the line of the leg the way a strapped heel would, so it makes your legs look long and depending on measurements of the foot and height of the heel can still be quite comfortable.

Knee-length Boots


You can wear knee-length boots with skirts and dresses and opt for a flat, heel or wedge depending if you’re trying to elongate legs.



Mules are a terrific option for adding heel but still maintaining comfort and not breaking the line to elongate your leg.  And a chunky heel will make your ankles look thin in comparison, but not overwhelm the foot.


You can also opt for a flat mule and there are many cute options out there since this style shoe is trending.



Wedges are an easier way to stand tall without wearing heels.  Opt for nude flesh-toned wedges that match your skin color it’s a great way to make your legs look longer.



If you want to know how to wear a dress with sneakers, there’s no shortage of inspiration on our Pinterest board. In many offices, sneakers earned HR’s stamp of approval, and even for date night, sneakers help create the casual-chic aesthetic that many of us strive to achieve. And with the influx of high-end and statement kicks now on the market, it’s easy to find a pair that works with some of the fancier pieces in your wardrobe.

Ankle Boots


If you think up a list of true wardrobe staples, ankle boots will undoubtedly be somewhere around the top but the way we wear them has been updated this fall.  Good news is that wearing ankle boots with skirts and dresses is fashion approved! More inspo found here.

Before you go, be sure to leave a comment and let us know your favorite go-to shoe brand that’s all about comfort and style.

Or maybe you have a styling tip to share with Kim on wearing dressy outfits with comfy shoes.

All of us women want to hear from you – so please please leave a comment now!

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