Look into the White’s Oxford or Derby. https://shop.whitesboots.com/all-boots/ I’m also a big guy with big feet and I was in Retail management for nearly a decade, and I would not recommend Redwing for comfort. We walk literally miles every day on concrete covered in linoleum, and that is not comfortable in any redwing I’ve worn that would also look nice enough to wear in management. (A big wedge sole moc toe boot is not going to fly for most managers) The White’s have a classic dressier look and have huge slabs of leather as the footbed that eventually conform to your foot. They also will last ages and can be resoled when they begin to wear down. The only downside is the cost and possibly wait time, but I think it’s more than worth it for the comfort and longevity.

I’ll try that thank you!

Yes, approximately 2 times longer woth 2 pairs or 3 times longer with 3 pairs.

My boyfriend had a pair of Caterpillars that’s lasted about 4 years as both work and daily ware shoes. I’d highly recommend them

Changing shoes every 3-4mo for 50h/week seems excessive perhaps. Look at their soles and see if there's issues there maybe. I suspect that no "better shoe" will fix that since you tried quite a few decent brands.

I don’t know enough to give you an answer but I do know that most of the suggestions you’ve gotten so far are just more consumer brands. My recommendation to you is to repost this in r/goodyearwelt because there are people there who actually do know.

I mean it looks pretty simple to narrow down.

If you disconnect the entire hose assembly from the body does it still whistle? What about if you put your hand partially over the mouth to obstruct the air? If it still whistles it’s in the body. If not, it’s in the hose somewhere.

If the sound is in the hose assembly, start at the far end and remove parts until the sound goes away. If it still whistles with only the hose attached it’s probably something stuck in there. Your handyman, handy neighbor, plumber, or electrician has a tool they can push through there real quick.

Thank you!

Check out SAS shoes on Zappos. I used to work in food service, and I wore their black slip resistant shoes. Best pair of shoes I’ve ever owned. I have bad feet, and I have tried lots of brands, and SAS was the winner. They also have a wide range of sizes, including 14s. I don’t know where you live, so there maybe an SAS store near you. They are not cheap, but as you have discovered, you get what you pay for.

Someone else mentioned this brand I’m going to go look into them!

I’ll look at Ecco, rockport didn’t have his size which was kind of a bummer

I wouldn’t expect designer brands to be made to last. The point of fashion hinges more on throwaway culture.

I've never heard anything about Tommy Hilfiger being 'buy it for life' quality. But maybe things have changed since the fad of Tommy (90's-early 2000's)

Good to know!

Thank you I’ll look into them now!

Former server here. We all swore by Dansko. They are comfortable and last long, but kinda pricey. We had an outlet store about an hour away we’d travel to just to get new ones, which we didn’t need to do often because they lasted.

There might be something in the tube that’s causing the whistling. Push something through the tube and make sure it’s clear

I second Red Wing, and also their insoles. Just don't make it a gift. He's got to be sure of the size because their return policy sucks.

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I don't know if they have slip resistant soles, but I've always gotten a lot of life out of ecco shoes.

That's always been my guess. I had a middle school teacher tell us about sneakers decades ago. My guess is that overtime mildew bacteria Etc grows into the fibers at a microscopic level and slowly breaks them down.

But that's just I guess. Whatever the reason is I can tell you that it works. I rotate between two pairs of shoes right now. Both Brands and models I've used for years. Individually one of them last about a year and the other about 2 years. I've had this two pairs of shoes for about 5 years now.

Do you (or anyone else) know what rotating helps them last? Is it that the materials have time to dry between wears?

Just get a Sebo Automatic X7

That’s a good suggestion thank you!

A lot of Red Wing Shoes last a very long time. My experience is no matter what if they're dress shoes worn every day they're going to wear out pretty quick. Shoes last a lot longer if you rotate through two to three pair of them.