Style Q&A: A Stylist's Picks for Comfy Shoes + Boots

comfy shoes and boots
I want recommendations for seriously comfy shoes [flats and boots] that don’t look terrible!
— Elizabeth Thompson

You know the old saying, “You get what you pay for?” Well, this has never been truer than when it comes to talking shoes. I know so many women (including my past self!) that live by stocking up on a million pairs of "affordable" shoes, only to find out they were 1) super uncomfortable for long periods of time and/or 2) fell apart after just a few months.

Of course, there are always exceptions to this rule and I do advocate for looking at a variety of stores because you never know when you’ll come across something that is super high quality where you don’t expect it. But...

If you are going to spend money somewhere, then shoes should 100% be where you invest in high quality stuff.

Have you ever had a cheap version of wine or chocolate? It's excited because you got such a good deal. But then you splurge on the good stuff and it tastes soooo much better? It’s the same with shoes. If you tried on, side by side, a pair of quality shoes with one that is poorer in quality - you will immediately be able to tell the difference.

True story:

A client of mine loves comfy shoes. In fact: she NEVER wears heels, so when we were shopping earlier this month, it was a hunt for cute and comfy flats, boots and brogues/oxfords. When we had our shopping session at Nordstrom I went straight to brands I knew would be well made + designed for comfort. She tried on Paul Green, Marc Fisher, Kork Ease, and Ugg. She loved them all. On a whim, she wanted to try a pair of Caslon - a fine, $80 cute shoe. She put them on and immediately took them off - they hurt, the foot bed was flat, and her words were, "Wow, these are definitely not as well made as the others!" Flash forward to today and she’s ordered about 10 zillion pairs of Paul Green’s (seriously, I should have bought stock in this company) and says, “These Paul Green booties basically make me feel like I’ve died and gone to heaven.”

Now, not everyone has a huge budget for shoes. BUT, I would put forth that when you can switch your thinking from, "Let me buy a cheap pair of shoes now and a cheap pair of shoes later", to "Let me invest in ONE pair now for later," you’ll have the money for that more expensive, quality pair.

When I purchased my Vince Camuto boots, I thought long and hard about the color, style, and heel height I wanted. I knew I wanted something neutral enough to wear with everything and a heel height I could walk days in while still looking good (my ideal shoe heel height for walkability is 1-2", no more). I spent about $120 on these boots (they ended up on sale) but they still look just as good into their second season as they did the first year I bought them. I invested in scotch guard to protect them from the elements and literally wear them with everything. I plan to re-sole and shine them up each year. I could have spent $40 on Target boots, but I would be buying a new pair every year and they would def not look as good as mine still do.

When you buy good quality shoes with the intention of wearing them for 3-5 years, it becomes easier to spend $80-$200 (+) on something that you will literally wear every day or at least several times per week. Here area few other reasons why you should invest in good shoes:

  • They take you where you need to go - you rely on them every day, so you should invest in something good
  • They support your entire body weight
  • They look + feel good
  • They make you feel like a million bucks which projects onto your confidence

Without further ado, here are a stylist's picks for comfy shoes + boots!


Marc Fisher

Sam Edelman

Vince Camuto




Kork Ease

Paul Green

Stuart Weitzman