Needing Opinions on the Right Shoes

[DaddyP]

Hello, everyone. I've a bit of a dilemma, and I was hoping to gain some perspective from you all.

Let me start with a brief bio. I'm a 40 year old banking professional based in the lower Midwest of the U.S. For years, I worked in a rural setting, where jeans, khakis and polls were the norm. I recently changed jobs, and I am now based in a larger metro. My client base has changed from small business owners and farmers to high net wealth, middle market business execs and investors. The current office dynamic is quite casual. Think chinos, button downs or polos, and a lot of loafers. But, I visit clients a couple of times a month, which requires a jacket at minimum. I also believe in dressing for the job you want, as well as dressing just a notch above the office average, so I have a tie and/or jacket a bit more than most. My wardrobe from the previous job is a bit ragged, and I've decided it needs a change. I've added a few things, but am currently in need of some better shoes.

My current shoes are a pair of black derbies I picked up on the cheap when starting this job. My biggest issues are they aren't all that comfortable and they don't really match my needs or clothes that well. They work with a charcoal grey suit, and maybe my olive slacks, but that's about it. They just seem limited. So, what would be a better fit? A dark brown set of derbies or oxfords? Something else? I do have a pair of mahogany loafers, so that side is covered.

 

[rjc149]

I would go with brown derbies. Brown oxfords are sort of contradictory.

 

[SartoriaModerna]

brown derbies +1. You can dress it up and down.

 

[SteveMc]

Brown derbies will give you the versatility you need.

 

[db530]

Longwings!

 

[DaddyP]

brown derbies +1. You can dress it up and down.

Sorry for not getting back to you sooner. Thanks for the reply. I was kind of thinking that, but I'd been eyeing a pair of chocolate brown oxfords I found at the time. I decided to hold off until I can find a good pair of derbies instead. I appreciate it.

 

[Testudo_Aubreii]

Welcome to SF! Is this it, or do you also plan to buy other pairs later? I don't recommend having only three pairs of dress shoes (black blüchers/derbies, mahogany loafers, and this potential new pair). Leather shoes need more rest than that. I'd try to get a fourth pair no more than a year after picking up this one. Anyway, probably the most versatile third pair, given what you've got, would be a dark brown smooth calf split-toe blücher/derby on an elegant last. Alden has one with a chunkier split-toe stitch.

Spoiler

Allen Edmonds has a more finely stitched one, the Delray. But AE don't have it in a dark brown. The Dark Chili Delray is definitely worth a look, but maybe a little too light a color to be a truly versatile third dress shoe. If you're getting a fourth pair in a year, that's less of an issue. More important is that it might overly resemble your mahogany loafer: depends on what shade of mahogany. (I think AE's other Norwegian split-toe, the Denali, is on too chunky a last to be versatile. It's more a weekend/tramping shoe than an office shoe. Okay for casual Fridays, but not the best for looking sharp.)

Before all that, though, I'd figure out fit. If those black derbies don't feel comfortable, it's most likely because they don't fit your feet well. My guess is that the last, size, and/or width isn't working for your feet. Well-fitting men's dress shoes are comfortable all day long, and that's even if the construction is just okay. In the afternoon/evening, when your feet are bigger because you've been walking, the shoe should fit close (but not pinch) all over the foot, except at the top of the toe box (where you can, and might want to, have room) and in the front of the toe box (where you need some room). There's a lot that goes into shoe fitting. The foot length from heel to ball joint, the width at the ball joint, the length of your toes, whether your first or second toe is longer, the height of your instep, whether you have high arches or flat feet, do you overpronate...The nice thing about AE is that they have 60 stores all over the US with staff that can help you understand your feet, and how AE's many lasts, sizes, and widths can or can't do well by them. You may find that your feet rule out long and sleek lasts, and instead call for more comfortable lasts like Alden's Modified Last. If you can get there, Moulded Shoe in NYC are folks who really understand comfort and fitting difficult feet.

But AE folks should be able to do pretty well by you. I'd look for ones who are really into measuring, thinking about the shape of your feet, and what lasts, sizes, and widths would work best for them. AE can even get you a different size or width for each foot. (Many of us have one foot a half-size or width different than the other.)

This is why I say fit first. Because the 108 last, on which AE makes the Delray I suggested, is both narrow and flat in the toebox. If your fourth toe sticks out to the side, or your toes are tall from the toepad to the toenail, it likely won't fit well. You might be better off on the 511 last. Etc.

That's a lot to chew on. But the hunt for well-fitting, good-looking, well-made shoes is a lot of fun. The take from the hunt never comes out perfect. Not even with bespoke shoes (though those can get pretty close!). But the results are miles better than what you can get from mass-market footwear and the "You're-a-size-9-shoe" mentality. For those of us in the hunt, our feet and calves are thanking us. So too, as we age, do our backs. And we look sharp.

 

[DaddyP]

Welcome to SF! Is this it, or do you also plan to buy other pairs later? I don't recommend having only three pairs of dress shoes (black blüchers/derbies, mahogany loafers, and this potential new pair). Leather shoes need more rest than that. I'd try to get a fourth pair no more than a year after picking up this one. Anyway, probably the most versatile third pair, given what you've got, would be a dark brown smooth calf split-toe blücher/derby on an elegant last. Alden has one with a chunkier split-toe stitch.

Spoiler

View attachment 2033967

Allen Edmonds has a more finely stitched one, the Delray. But AE don't have it in a dark brown. The Dark Chili Delray is definitely worth a look, but maybe a little too light a color to be a truly versatile third dress shoe. If you're getting a fourth pair in a year, that's less of an issue. More important is that it might overly resemble your mahogany loafer: depends on what shade of mahogany. (I think AE's other Norwegian split-toe, the Denali, is on too chunky a last to be versatile. It's more a weekend/tramping shoe than an office shoe. Okay for casual Fridays, but not the best for looking sharp.)

Before all that, though, I'd figure out fit. If those black derbies don't feel comfortable, it's most likely because they don't fit your feet well. My guess is that the last, size, and/or width isn't working for your feet. Well-fitting men's dress shoes are comfortable all day long, and that's even if the construction is just okay. In the afternoon/evening, when your feet are bigger because you've been walking, the shoe should fit close (but not pinch) all over the foot, except at the top of the toe box (where you can, and might want to, have room) and in the front of the toe box (where you need some room). There's a lot that goes into shoe fitting. The foot length from heel to ball joint, the width at the ball joint, the length of your toes, whether your first or second toe is longer, the height of your instep, whether you have high arches or flat feet, do you overpronate...The nice thing about AE is that they have 60 stores all over the US with staff that can help you understand your feet, and how AE's many lasts, sizes, and widths can or can't do well by them. You may find that your feet rule out long and sleek lasts, and instead call for more comfortable lasts like Alden's Modified Last. If you can get there, Moulded Shoe in NYC are folks who really understand comfort and fitting difficult feet.

But AE folks should be able to do pretty well by you. I'd look for ones who are really into measuring, thinking about the shape of your feet, and what lasts, sizes, and widths would work best for them. AE can even get you a different size or width for each foot. (Many of us have one foot a half-size or width different than the other.)

This is why I say fit first. Because the 108 last, on which AE makes the Delray I suggested, is both narrow and flat in the toebox. If your fourth toe sticks out to the side, or your toes are tall from the toepad to the toenail, it likely won't fit well. You might be better off on the 511 last. Etc.

That's a lot to chew on. But the hunt for well-fitting, good-looking, well-made shoes is a lot of fun. The take from the hunt never comes out perfect. Not even with bespoke shoes (though those can get pretty close!). But the results are miles better than what you can get from mass-market footwear and the "You're-a-size-9-shoe" mentality. For those of us in the hunt, our feet and calves are thanking us. So too, as we age, do our backs. And we look sharp.

No, I intend to get a couple more pairs, probably some chukkas and chelseas. With the pair of brown derbies, I will eventually replace the black ones. That amount should be OK, as my work situation has changed to a permanent hybrid environment; three in office, two out.

Unfortunately, you are correct about the wrong fit. I tried to take my measurements at home, by myself. I got the sizes too small and bought a 12 based on that. A bit after this post, I went to a local shoe store/cobbler down the street from my work. He measured me out as a 12.5 on one foot, both on total length and instep, and just below a C width. The other foot is a clear 12 and solidly a C. Unsurprisingly, the foot that hurts the most is the 12.5. It's rather squeezed in the toe box by the end of the day.

 

[Testudo_Aubreii]

Yeah, it's quite hard to measure your own feet properly. If you are a C width, you should be able to fit into narrower lasts, although instep, foot curvature, and your toes' shape matters a lot. The AE 108 last on the Delray has a serious banana curve from the waist to the toebox (we sometimes call that a "half-banana last"). See the sole pic of the Delray on AE's website. Sole pics are the best way to see a last's 2D shape. Top-down pics of the last itself help you with the 3D (instep shape, etc.) A half-banana last like 108 can work for people with feet with an inward curve from the arch to the ball. Not so well for those without. Alden's Aberdeen last, which is their narrowest and pointiest, and is the last for the split-toe I showed above, doesn't banana as much as the 108. It's less curved. If your feet don't curve much (like mine) Aberdeen is probably better than 108. And Alden Hampton maybe better still, because it gives more side room to the big and fourth toes. But, for those needing lots of arch support, Alden's Modified Last, a "true banana curve," is often good, because it allows for a close fit at the arch. And unlike 108, it leaves room for the pinky and fourth toe.

Most people do have one foot almost a half size different than the other. In that case, we try to fit the larger foot. But if you're a true half-size difference, AE should be able to get you split sizes. Don't know about Alden and split sizes.

Some good comparisons of AE and Alden lasts and sizing here (he complains about 108's narrowness, I think because of that pronounced curve from the waist).

P. S. Good insights on AE's lasts here.

 

[The Noble Dandy]

I also believe in dressing for the job you want, as well as dressing just a notch above the office average

Music to my ears. How I wish that more men had attitude like yours.

Now, back to the shoes. As everyone else suggested, a pair of brown derbies would be your best choice here, I think. Just don't forget to also buy some wooden shoe trees which will prolong the life of those shoes and keep them in shape.

 

[DaddyP]

Already done. I want whatever I get to last foray years to come. I've already learned the ins and outs of cleaning and polishing, and do so on the regular.