Reader Question: Stylish, Comfortable Men’s Shoes for a Business Casual Setting?

Reader Question: Stylish, Comfortable Men’s Shoes for a Business Casual Setting?

By Megan Collins | Last Updated: Jun 23 2022 | 3 min read

Evan asks:

I work on my feet a lot, and I have to be in stylish, business-casual attire. I’ve found plenty of shoes that look great but start to hurt after a few hours standing. And I’ve found plenty of shoes that stay comfortable through the grind but look like they are made for the elderly.


Are there any business-casual shoes out there that look AND feel great?


A solid question, and one I get from a lot of guys. Obviously you want to look good at work, but not at the expense of your dogs barking at the end of a long day.

(…Of course, while I maintain that until the trend in guys’ footwear includes a 3-inch stiletto heel, you don’t really know what painful shoes feel like, but I need to at least feign empathy. I know. You’re welcome.)

So I checked in with the experts on this one, and here’s what I found out:

“Mens’ shoes are always stiff at first, but then should become more comfortable,” says Dr. Ira Meyers, a podiatrist in Hungtington Valley, Pennsylvania. Luckily, brands are getting on board with the idea that while a dress shoe needs to ultimately keep its form (and so by necessity is somewhat rigid), it can – and should – cushion your feet as well.

Cole Haan was one of the first brands to understand dress shoes’ dual functions, integrating Nike Air technology into several of their men’s and women’s lines. Shmancy sports cushioning in the shoes increases support, which is what keeps you from wanting to trade your shoes for flip flops by 3 o’clock.  The LunarGrand line offers a fashion forward look. However, most Cole Haan shoes ring in between $250-$300, and while Evan, you didn’t add a price range, I wanted to keep things a little less expensive if possible.

For his patients, Dr. Meyers recommends brands like Florsheim, Bostonian, Johnston & Murphy, and Rockport. Like Cole Haan, these more old-school brands are starting to trick out their work shoes with technology traditionally reserved for your workouts. Rockport, for example, uses cushioning by Adidas in its dress shoes for added comfort.

As for the looking good part, I browsed Meyers’ brand suggestions and picked out my faves for you.

Johnston & Murphy offers four lines of “comfort fit” shoes; my favorite was the Optima line, which offers a cushioning system and full leather linings that should keep your feet cool and comfortable.

Since Bostonian is part of Clarks, I looked over there to see what they had, (Bostonian’s selection was a little stuffy/old-man-ish). Some of the models boasted an “Ortholite® footbed” which sounds like you should be sleeping on top of them, but again, offers more cushioning than a regular dress shoe.

My picks, in black and brown:


1. Florsheim, $120
2. Rockport, $135
3. Bostonian, $160

1. Florsheim, $105
2. Clarks, $140
3. Johnston & Murphy, $175

Meyers also suggested investing in shoe trees, to help your shoes keep their shape. Read more on my love of a good shoe tree here.


Meyers stressed the importance of trying a shoe on. If it’s not comfortable when you first put it on, it’s not going to be comfortable at the end of a long day on your feet. You can go sneak your feet into Clarks, Florsheim, and Rockport at Nordstrom, while Macy’s carries Bostonian, Johnston & Murphy and Rockport.

Now you tell me:

What shoes have you found look stylish AND feel comfortable all day? Leave your own reccos in the comments!


I started Style Girlfriend to help guys look, feel, and act their best.