6 Best Dress Shoes for Fat Guys

6 Best Dress Shoes for Fat Guys

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If shoes make the man, then I have always struggled to find my manhood. I have always worn my shoes until they literally fall off my feet, or the soles are so full of holes I might as well be wearing sandals or going barefoot. The problem is, why do my shoes wear out so darn fast?!

Finding shoes as a big guy can be difficult, especially when you want something other than sandal loafers or velcro athletic shoes. Add that to the fact that the best shoes for fat guys are normally off-the-charts expensive (or just funny looking), and you have a recipe for wearing poor quality shoes that hurt your feet. On the off chance that you do find a well-fitting shoe, what are the odds that it is in your price range, and more importantly, made well enough to last more than a few months? Pretty low.

Well, don’t worry! We have beat the streets and put in the footwork (haha) necessary to make this happen: to find the best pair of dress shoes for large and heavy guys that will both look awesome and stand the test of time.

Why do your shoes keep falling apart??

All of my research has come up with two real reasons that big guys cannot keep their feet in shoes: improper fit and inferior shoe quality. Sound simplistic? It should be. But let’s take a closer look and see why these issues even exist:

Improper Fit: If you are a bigger guy, odds are that you also have wide (or extra wide) feet. Most guys who struggle to find shoes that are actually comfortable end up settling for a typical “wide width” shoe from a generic supplier, never realizing that shoe widths vary wildly from maker to maker – and that choosing the wrong width is bad for both your feet and your shoes. If a shoe is too narrow, you stress all the seams in the shoe, which typically ends up causing either a seam to come unstitched or the sole to come off of the upper. Not only that, but the shoe/sole that is too narrow for your foot can cause you to have an uneven gait and wear through heels extremely quickly. Luckily, almost all of this is corrected with the proper fit.

As a side note, I fall into the camp of getting lazy and buying shoes that are too narrow for me. My real shoe size is a 12W, but I normally end up buying a size 13 because it’s so much easier to find. Don’t be me.

Poor Shoe Quality: As my grandpa used to say, “they sure don’t make things like they used to!” Typically this is actually a good thing, but in the case of shoes, it can cause serious issues. These days, “affordable shoes” are typically made of poor quality leather and held together mostly by glue. I used to be of the opinion that, since I wear out shoes so quickly, I should probably just buy cheaper shoes more often. That was a mistake. If you wear out shoes more quickly, the answer is actually to buy a more expensive shoe!

Expensive, high-quality shoes have two main advantages: they are made of better materials so they last longer out of the box, and they can be repaired! I have a pair of Allen Edmonds that are now 6 years old and just look better with age. During that time, I have had 2 new heels put on by a cobbler and 1 seam restitched when it came undone. My $300 pair of shoes have ended up lasting me 6 times as long as the shoes I used to buy, and have looked better doing it! (If you are curious about the price differences between repairing and buying, check out this article on BespokeUnit).

So now that we know of the general problems which plague plus size men and their shoes, let’s look at some that will solve these problems!

Best Choice
Neil M Men's Wynne Oxford
Florsheim Men's Midtown Plain Toe Oxford
Best Price
Hush Puppies Men's Leverage Slip-On
Allen Edmonds Men's McTavish Oxford
Rockport Men's Essential Details Waterproof Wingtip Oxford Shoe
Allen Edmonds Men's Park Avenue Oxford
Brand
Neil M
Florsheim
Hush Puppies
Allen Edmonds
Rockport
Allen Edmonds
Model
Wynne Oxford
Midtown Plain Toe Oxford
Leverage Slip-On
McTavish Oxford
Essential Details Waterproof Oxford
Park Avenue Oxford
Best Choice
Neil M Men's Wynne Oxford
Brand
Neil M
Model
Wynne Oxford
Florsheim Men's Midtown Plain Toe Oxford
Brand
Florsheim
Model
Midtown Plain Toe Oxford
Best Price
Hush Puppies Men's Leverage Slip-On
Brand
Hush Puppies
Model
Leverage Slip-On
Allen Edmonds Men's McTavish Oxford
Brand
Allen Edmonds
Model
McTavish Oxford
Rockport Men's Essential Details Waterproof Wingtip Oxford Shoe
Brand
Rockport
Model
Essential Details Waterproof Oxford
Allen Edmonds Men's Park Avenue Oxford
Brand
Allen Edmonds
Model
Park Avenue Oxford

The Best Dress Shoe For Big & Heavy Guys

best shoes for fat guys brown dress shoe
Neil M Men’s Wynne Oxford

The number one shoe we recommend for big guys is the Wynne Oxford. Well, we actually recommend most shoes from Neil M, but these are the nicest and best looking! My pair has been hanging around for about 3 years now, but most guys of 350 pounds or more are getting at least 5 years of wear out of them! Check out this review:

I bought a pair of these Wynne oxfords in Cognac 5 years ago. I am over 350 pounds and have worn these shoes 50 hours a week. They are so comfortable even now that I have a hard time finding shoes to compare with them.

I have been afraid to reorder because some folks have expressed concerns with them not being the same quality. Today I received my new pair of Wynne Oxfords in worn Saddle, size 14D, the same size a bought 5 years ago. They are gorgeous! Fit me exactly the same and are way better looking than the Cognac.

My last shoes squeaked a little the first couple of weeks I had them, I expect the new ones will as well. Remember, this is not a 12 month shoe I have worn mine without issue for 320 weeks. 2 weeks of squeaks is nothing to worry about.

I bought a pair of the famous Rockport Margin in 15w at the same time and they fit exactly the same as this in 14d. Side by side isn’t even fair to compare them, the Neil M is just a nicer shoe. Looking forward to another 5 years of comfort. Actually going to re-sole my old ones, the leather still looks great.

-AC (spelling corrected)

Put simply, this is the best shoe available for big men and, lucky for us, it costs less than half of what most high-end shoes cost! Yes, they may set you back a bit, but image having the most comfortable pair of dress shoes that you’ve ever had, and not needing to worry about them for the next 5+ years! In fact, if you resole and care for them well (or just have them in multiple colors), I would not be surprised if you didn’t have to worry about shoes for the next decade or more.

What I love about this shoe:

  • It is available in widths from narrow to extra-wide, ensuring that everyone has a properly fitting shoe that will last.
  • It is made from waterproofed 100% bison leather, some of the toughest shoe leather there is!
  • It has a removable footbed with gel dampening, get ready to walk on clouds…
  • It has a leather and Drilex lining. This does two things: it keeps the shoes breathable so you don’t have stinky, sweaty feet, and provides a comfortable, but hard-wearing inner surface.
  • They have a rubber sole which is firm, grippy, long-lasting, and cheap to get replaced.

If you haven’t noticed, I’m a major fan-boy of these shoes. But don’t judge me too hard until you’ve tried them for yourself, I can guarantee that they will be pleasing to the snobbiest of shoe snobs.


The Best Dressier Shoe for Big & Heavy Guys

best shoes for heavy guys
Florsheim Men’s Midtown Plain Toe Oxford

If you want a shoe that is a bit shinier and easier to dress up than the Neil M’s, then you should check out Florsheim. Specifically, their Midtown Plain Toe Oxford. It is an absolutely beautiful shoe that is available in black or brown, not to mention widths up to XX-Wide! The well cushioned and removable footbed will keep you comfortable no matter how long you are on your feet during the day. While this shoe is not quite a durable as our #1 recommendation, it is a very nice shoe that can be had for almost half the price.

The Best Budget Slip On Dress Shoe For Heavy Guys

best cheap dress shoes for big and wide feet

If you’re in the market for a slip on dress shoe for big guys, the Hush Puppies Leverage shoe is probably your best option. I don’t know why it is that big guys insist on wearing slip ons, but I almost always advise against it. They don’t look as nice and they rarely fit as well. I have even seen sad, overweight fellows who have cut all the way down the elastic stretch panels to try and get normal width shoes to fit their fat feet. Well, worry not, this full grain leather shoe is available in both wide and extra wide widths to make sure your toes are comfortable. While this is an extremely comfortable shoe, expect it to develop very noticeable creases where your foot bends.

Best Higher End Dress Shoe for Big & Heavy Guys

best looking dress shoe for big guys
Allen Edmonds McTavish Oxford

It isn’t possible to have a “best of” any type of dress shoe without at least one pair of Allen Edmonds making it onto the list. While their cost puts them out of reach for most casual work goers, those who are serious about either foot fashion or foot comfort should definitely look at this shoe.

The Allen Edmonds McTavish Oxford is literally one of the best and longest-lasting dress shoes that you can buy, no matter your size. Their expansive range of sizes and widths makes sure that your foot will be comfortable and your shoe will be long-lasting. Very high-quality leather that is crafted into shoe shape right here in the USA should seal the deal if you want the best.

Best Budget Dress Shoe for Big & Heavy Guys

fashionable wide dress for big men
Rockport Essential Details Wingtip Oxford

In this line-up, there’s really nothing special about this shoe. It is an above-average quality shoe that is available is wide widths, looks great, and will be comfortable for years. If you find it on sale, however, it can be the cheapest shoe on this list. 100% waterproof treated leather in a shoe at this price point (that still breathes) is an excellent deal. I own a pair of these shoes, and they see the outside world every time the weather turns nasty and I want to keep my shiny shoes in the garage.

Another Awesome High-End Dress Shoe for Heavy Guys

big guy dress shoe
Allen Edmonds Men’s Park Avenue Oxford

Made with premium calf-skin lined uppers and a full leather sole, it’s obvious that this is both a nice and expensive shoe. But you could probably tell that just by looking at it. It might seem unnecessary to include a second pair of Allen Edmonds, but remember you judge a man by his shoes. If you are a big guy that wants instant clout, then investing in your image (by buying this shoe) is a bold move. It is available in 4 different widths from a men’s size 6.5-14. While this is a high-quality shoe that will last for a good amount of time, if you are looking for a shoe to put lots of miles of and stand in for long periods of time, this probably isn’t it. If you want to look amazing and have some wiggle room for your toes while you sit behind a manager’s desk, get yourself a pair of Allen Edmond Park Avenue Oxfords.


Best Dress Shoes For Heavy Guys

What makes a good dress shoe?

While we have given you our top suggestions, maybe none of these were quite what you were looking for. In that case, you may be wondering what you should look for in a good dress shoe for plus-size guys. Well, here are 4 tips that will help ensure that you get a high(er) quality shoe:

  • Avoid Synthetic Leathers. Leather comes in various grades (and corresponding prices). As you go further down the spectrum of quality, you get a shoe that has thinner material, is typically less soft and comfortable, and will wear out faster. Look for Full Grain leather as it is made from the top (toughest) part of the cowhide. This is the only type of leather that isn’t sanded to remove imperfections, so the shoe-maker typically chooses hides with fewer imperfections to begin with for this type of shoe. Next up in the quality line-up is Top Grain leather, followed by Genuine Leather.
  • Look For Stitched Soles. There are only two ways that soles are connected to the uppers: stitching or cement (glue). Stitched soles (usually used in combination with glue) are typically much stronger and a sign of higher quality shoes. If you cram overly wide feet into a pair of glued shoes day after day, the stretching and twisting will eventually cause the sole to break away from the uppers.
  • Look For Replaceable Heels. If you buy a high-quality shoe, there isn’t much a cobbler can’t fix on it. He can replace heels, put on entirely new soles, replace insoles, restitch, polish, condition, etc. If you tend to wear though heels quickly or unevenly, look for shoes that have a sole that could be replaced independently on the entire sole. Also, look for shoes that have a “normal” sole and not a proprietarily shaped sole that is integrated into the shoe:
heel comparison on the best dress shoes for fat guys

People who claim to have the best dress shoes for fat guys really like to have a “specially shaped sole” or a uniquely shaped heel which really does only one thing: prevent you from repairing the shoe so you have no choice but to buy another when they wear out!

  • Choose a Shoe that is Easy to Polish/Condition. The easier it is to polish/condition the leather on your shoes, the more likely it is that you will do it on a regular basis. And the more regularly you care for your shoes, the better they will look and the longer they will last. Smooth-toe shoes with few seams and brogue detailing (such as our first recommendation) are the easiest to condition and slap a layer of polish on.
  • Find a shoe that comes in multiple widths. Makers of high-quality shoes are much more concerned with a proper fit that those who crank out shoes on a budget. For this reason, they are likely to offer more than one (and hopefully several) widths. Because styles and brands vary in width, you might need a medium width in one shoe and a wide or extra wide in another. Don’t be afraid to try several widths and return a pair of shoes that isn’t quite right for you.

How to care for your dress shoes to extend their life

As with choosing an easy-to-care-for shoe, we’ll try and make your overall shoe care something that you can do quickly and easily. In something is more onerous or time-consuming it *might* be better, but it’s also less likely that it will actually happen. So let’s choose 2 quick care items that are simple to do (and will keep your shoes alive):

  1. Buy shoe forms. While shoe forms may seem to be for snobby, rich people – the snobby, rich people have it right. Shoe forms serve two crucial functions for your shoes: they maintain the shoe’s shape, and they soak up leftover foot moisture. Those two functions will help your shoes last longer, look better, and not smell terrible. We recommend that you get yourself a good quality (don’t go overboard, wood is wood) pair of cedar shoe forms (I use Stratton Forms which you can pick up in a 2 or 3 pack here!)
  2. Polish your shoes. Spending 10 mins on your shoes once or twice a week will keep the leather clean (dirt kills) and will prevent it from drying out. Hopefully, you know how to polish your shoes. If not, The Art of Manliness has a good guide. Just grab some quality (but budget) polish and buff it out!

My Recommended Price-Conscious Shoe Shine Kit

Plus Size Men Dress Shoes Fashion Tips

big guy fashion tips for belt and shoes

Choosing a color of dress shoes shouldn’t be a daunting task. I’ll simplify it for you, get both a brown and black pair. Your shoes will last much longer if you rotate them, and you’ll always be able to match them up with what you’re wearing. I would advise against buying any different or unusual colors until you have both brown and black shoes in your high-quality arsenal.

Once you’ve found your shoe and picked a color, repeat the following mantra with me: “Shoes to belt, pants to socks. When I was much younger, I wore a hand-me-down black belt to church every week. That was fine when I only had a pair of black shoes, but when I grew out of those and started on a pair of hand-me-down brown loafers, my bishop pulled me aside and gave me a quick lesson in how to dress.

Wearing socks that match your pants can help make your legs look longer (a plus if you’re plus-size…) and looks much more professional. A belt that matches the color and tone of your shoes will pull your entire outfit together and make it look much more cohesive.

Getting measured for shoe size

I’m going to go out on a limb here and assume that my childhood shoe experience was fairly normal. When it came time to get new school shoes we would head to the store, I would try on a pair that was roughly my size, and my mom would poke/pinch the end of the shoe to see where my toes were. This usually worked okay…but now that I’m an adult and my feet have stopped growing, I figured I would like to know what my actual shoe size is. Not only that, but there isn’t really a “pinch test” to find out if a shoe is too narrow.

Luckily there is a simple method you can use at home to figure out your shoe size and with. Check it out on WikiHow.

If you’ve gone through the effort to find out your shoe size/width and read some reviews, I would never be scared of ordering shoes online. Reputable retailers (such as Amazon) typically have a “no questions asked” return policy, so get your shoes, wear them around your house, and return them if they aren’t going to work out! Just remember, high-quality leather shoes can stretch a half a size or so, so if they’re close, keep them and let them shape themselves to your feet! All in all, it’s just easier to find dress shoes for big guys online than in-store.

The Best Dress Shoes for Fat Guys: Go level up your comfort and your style!

You now have all the information you need to get yourself an amazing pair of shoes that will look better, feel better, and last longer than any pair you’ve had before. Hopefully if you scroll back up to our list, you can find yourself the best dress shoes for fat guys that the internet has to offer! Happy shopping!

p.s. No matter how nice the dress shoe is, your foot type might need some extra cushioning or support. Check out our new article: The Best Insoles For Overweight Guys and Gals

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