@thedevilinablackdress
I think this very much depends on your own preference and definition of stylish. I think we forget on S&B that we really don't ask mean the same thing when we use this word! I wear trainers, chunky boots, brogues, chunky sandals. Brands like Camper, ECCO, Clarks, Solovair, ASICS. Therefore I don't struggle to find comfort within that. However, if your style is different, if you prefer heels or more formal / dressy / feminine styles, then I can see it will be more difficult.
It’s a complete myth that you have to choose between style and comfort
If you have 'normal', healthy feet and ankles, true. But not all of us are in a situation where something available on the High Street will meet both needs.
To give a personal example, I have relatively healthy feet in that I do not have bunions, corns, ingrowing toenails or calluses. I look after them. They're clean, well groomed, polished to perfection - and from the moment I walk in the front door from work, they're bare.
However, I also have multiple sites of bursitis in both the metatarsal and intermetatarsal joints, tendonitis, a very wide first metatarsal joint, one foot a good half size shorter than the other, high arches and simultaneously functional arch collapse (so not permanently flat, just when I'm standing for an extended period) and overpronation, all as a result of the glorious conjunction of Psoriatic Arthritis and EDS. They also vary significantly in terms of 'fatness', depending upon what's actually inflamed on any given day. Oh, and one ankle has a tendency to 'ping' and swell up like a balloon randomly.
The solution seems simple; wear nice shoes that accommodate those points. Not simple in practice.
[Gets measuring chart out]
Okay. I'm actually a 4.5 on the right and a 4 on the left. However, the width of my first metatarsal joints are 270mm. There is no shoe in existence, even in the specialist shops, that I have found that accommodates a foot that wide at that size. Men's shoes don't go down that small, children's shoes don't go that wide, women's shoes - well, I might as well just not bother.
The last shoe that sort of fitted was age 9 when I had a pair of Clarks Size 4 GGG fitting, where they sized up to get something that didn't crush my toes. Ever since then, every pair of shoes I have owned has hurt me one way or another, whether it's because they've been too big, too narrow, arch support is in the wrong place if it existed at all or they've just not felt right and I've ended up in pain somewhere or another by halfway through the day. The least painful options have been a pair of size 6.5 Men's walking boots (discontinued), a pair of size 6 Men's steel toecap boots with superthick mountaineering socks, as the lacing held the things on my feet and one pair of dayglo turquoise special edition size 7 Nike trainers for some reason.
I've had to adhere to workplace dress codes throughout that time, though. These do not allow for a set of clodhoppers or some luminous monstrosities at the end of my legs (no, plain black trainers never seem to feature in stores inventories when I need a new pair). I generally have been dragged in for some sort of disciplinary about my non compliance with dress codes at every job and the 'compromise' is generally that I keep my feet hidden on a day to day basis, wearing something vaguely conventional - but far too large - when meeting VIPs.
Whilst my employers want to accommodate, it remains that lots of people believe that style and comfort are not mutually exclusive concepts and they will make judgements of me (and my employer) if I do not look what they term as Professional.
I have a suspicion that either Crocs or a proper set of handmade wooden clogs with a heelstrap might answer most of my problems, but then again, Crocs are horrible and there's still the issue of ankle support. And diabetic boots aren't designed to provide support for actually walking and working - they're there as a extremely unattractive foot covering for people who can't feel what's going on in their feet.
If you can provide details of a retailer that can indeed make attractive looking footwear that also deals with my permanent disabilities and the sizing issues, I would love to hear about it. Or somebody who makes bespoke shoes without charging more than I earn in a month.