The Best Shoes for Overweight Men Wanting to Impress in 2020

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When I was younger, I always hated going to amusement parks or play areas where I had to take my shoes off. I wore fat-kid-shoes and I had funny looking toes. Not a good combination. Now, I’m still overweight, I still have funny toes, but I’m not longer ashamed when people see me pull my shoes out of my little cubby to put them on.

I don’t know why I didn’t solve my own problem earlier but, being a big guy, my shoes were always an issue for me. They didn’t fit very well which meant they were always worn out or misshapen, they were hard to get on so I always had to put on a show, and they sure as heck weren’t fashionable. I probably would have gotten fewer looks going barefoot, except that every single overweight guy in the area had the same type of shoes as I did and knew exactly how I felt. Well, fellas, it took me a while but I’ve cracked the code and found the best shoes for overweight men in every situation.

Spoiler: Overweight men need the right shoes…not special shoes. The best shoes for overweight men are shoes that fit.

Here’s the kicker, overweight men don’t need special shoes. In fact, big guys need the same things in a pair of shoes that everyone needs: proper fit. It just so happens that the shoes that fit most people don’t fit well if you’re a big guy with wide or high volume feet. Now, I will also say that big guys tend to wear shoes out faster and just don’t look good in some types of shoes. So, there are four things that, in my opinion, make the best shoes for overweight men:

Wide w/ a large foot box (or at least well-fitting). Before I actually figured out what size of shoe I needed my pinky toe spent a lot of time being squished and I actually wore out the side of several pairs of shoes. Long story short, I need a 12 Wide or Extra Wide but had just been buying size 13-14 my entire life. So, if you have had trouble finding comfortable shoes, get shoes that are the proper width, or at least have a wide toe box area so your feet aren’t getting pinched.

Durable. If you are one of those guys whose shoes wear out super fast, don’t be tempted to buy cheaper shoes just because you think they won’t last long anyway. If you find a shoe that actually fits properly and is made of high-quality materials there is no reason why you should wear shoes out faster than anyone else.

Not Dainty: As a big guy I try to avoid wearing shoes that are stereotypical of either overweight men (Walmart tennis shoes) or skinny hipsters. For example, Toms are super comfortable but they just make me look like a fat guy who wrapped some leaves around his feet. Now I’m not saying that you need big clunky shoes, but get a shoe that speaks for itself and has a presence. If that doesn’t quite make sense, hopefully it will click when you see some of the options I found!

Proper sole and footbed materials. One of the most common failure points of shoes is the sole and footbed. This isn’t necessarily a big man problem. Nearly everyone will eventually wear out the sole but, since big guys exert more force, the problems manifest faster. If you’re going to be walking much or spending days on your feet, opt for rubber or leather soles which won’t deform or break apart quickly.

Now, most of those items are common sense. So why don’t overweight guys have better-fitting shoes? Well it’s because we have a hard time finding well-fitting shoes in stores! When I need shoes, I can’t just go to the mall. The shoes won’t fit, and they won’t last. These days, most guys need to be buying shoes online. There are more options and you are almost always able to find your size. And if they don’t fit? Pretty much everyone offers hassle-free returns.

As I mentioned in my article on the best insoles for big guys, you’ll find very polarizing reviews when it comes to foot products (insoles, shoes, and even socks). Typically, if you see some very angry one-star reviews, it’s not because the product was terrible. It was just the wrong product for that’s person’s foot. So make sure to take reviews with a grain of salt and know that you have to find a shoe that works for you.

Best Everyday Shoes for Big Guys

Casual Athleisure Option

Skechers Men's Classic Fit-Delson-Camden Sneaker,black/Grey,11 M US

For most guys, Skechers isn’t the first name that comes to mind when it comes to shoes for overweight men. However, they probably should be! They make shoes in a variety of widths that allow almost everyone to find something that works for them. Additionally, these shoes have air-cooled memory foam cushioning and, the crowning achievement, they’re slip-on! Or, at least, they’re not lace up. People who are not overweight cannot fully appreciate that bending over to tie your shoes can really suck. While these shoes look like they are lace-up, they are actually elastic fit and the “laces” are bungees. So if you’re in the market for a great shoe that is comfortable, easy to put on, and fairly durable, pick up a pair of these! If they are not quite dressy enough for your everyday wear, keep reading!

Dressier Daily Wear

Nunn Bush Men's Bromley Plain Toe Chukka Boot Suede Leather with Comfort Gel and Memory Foam, Tan Crazy Horse, 12 Medium

As an overweight guy, I have a bit more to overcome if I want to look fashionable. You can talk about body positivity and self love all you want but the fact remains, if I dress average, I feel below average attractive. Which is why I always try to stay one step ahead in my shoe game. A pair of chukka boots is a closet essential for every big man and these are one of the most affordable yet comfortable pairs on the market.

Boots such as these can be worn with just about any pair of slacks or big man jeans and can transform you from being just an overweight guy to being a husky manly man. If you’re looking for chukka boots, try to stick to those with a real sole (like these) instead of a foam or gum sole. Also, make sure you get a wide size if needed or the stitching that holds the sole on will be showing strain soon. I’ve worn the above boots for more than a year and the only criticism I have is that they need a bit more arch support (most chukka boots do) and new laces. You can find my review of the best arch support inserts for big guys here but you’re on your own for the laces.

Before I started making some conscious fashion choices, the above two shoes weren’t much like anything I wore. Then I realized that, unless I made a conscious choice to differentiate myself, I would end up looking like every other unfashionable fat guy out there. I naturally gravitated towards what was comfortable and easy. Since comfort is still important, I decided to put in the extra effort necessary to find shoes that were both versatile and fashionable as well. Both of the above options are extremely affordable, can go with a ton of different casual or dressy looks, and are available in widths to suit big guys and our chunky feet.

Your daily shoes should be matched to the type of activities you do. Do you walk a lot? Get the Skechers. Do you need to look more professional? Get the chukka boots. Do you need dressier shoes? Scroll down to the dress shoe section! Trust me, you don’t have to wear casual shoes to be comfortable. High-quality dress shoes can be just as easy on your feet!

Dress Shoes for Overweight Guys

Neil M Men's Wynne Oxford,Black,8 D

The best dress shoes for anyone guy who isn’t a stick (at least in my opinion) is the Wynne Oxford. My pair has been with me for 3 years and is only looking better with age. If that recommendation doesn’t sway you, I don’t know what would!

A Slip-on Dress Shoe For Overweight Guys

Hush Puppies Men's Leverage Slip-On Loafer, Black, 9.5 W US

I spent so much time researching the best dress shoes for fat guys that I wrote a complete article with several options. So I won’t beat a dead horse here. Suffice it to say that a good big man’s dress shoe will have all the same characteristics as other shoes we’ve discussed, with the addition that they won’t be high maintenance (polishing, etc.) and will look sharp with dress clothes. Both of the above options are a huge upgrade for the majority of men

The Best Running Shoes for Overweight Men

ALTRA Men's Olympus 3.5 Trail Running Shoe, Green/Orange - 10.5 M US

Finding running shoes for overweight men isn’t hard. There are tons of options that fit decently well. The problem is, they all last about 3 months before they’re absolutely trashed. The soles are worn out and the foam is crushed in, making them dangerous to wear. So the trick becomes finding big man’s shoes that provide comfort and support, won’t wear out quickly, and doesn’t break the bank. Sound like a dream? It is. And its name is the Olympus 3.5 from Altra.

Now, the Olympus is about twice the price I was paying for the running shoes I had before…but they have lasted more than 3x as long! If you don’t put many miles on them, they are not only the best running shoes for overweight men, but among the most affordable long term as they should easily last a year or more.

If you’re not quite up to running, you can check out my review of the best walking shoes for overweight men instead.

How much money should I be spending on shoes?

In my life, I have come to the realization that most people either spend way too much or way too little on shoes. On the one hand, people know that their shoes will wear out eventually (and they don’t really care how they look) so they buy the cheapest shoes possible. The people on the other end of the spectrum know that quality shoes will look better, be more comfortable, and last way longer. So they go way overboard and buy the most expensive shoes they can find, thinking that the price alone means that they must be the best shoes for overweight men. What they don’t realize, is that there is that there is a diminishing rate of return with shoes. Eventually, you just can’t pay enough to get a higher quality shoe.

So the answer to the question is, you should spend the smallest amount of money possible on shoes that actually meet your needs. They need to look nice, they need to fit well, they need to be durable, and you need to like them. Once that checklist is taken care of, there isn’t much beneift to buying more expensive shoes. However, if you are one f those people that has been spending the bare minimum just to have something to cover your feet with, you’ll be waell served (and save money in the long run) by making a larger investment in your feet.

In Conclusion:

You came here looking for the best shoes for overweight men and I gave you four awesome options. Scroll back up and pick one. Happy walking!

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