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Best dress shoe types and style with jeans

EZB

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I think this is heavily dependent on how fit/tall you are actually (as well as what size shoe you wear).

You can likely pick up a pair of vintage Florsheim Imperial Longwings, have them shipped to a reputable cobbler, and have them refurbished & resoled with JR, Vibram, or Danite, all within your budget.

That said, I’m 6’4 or roughly 192cm, so for me a lot of brogues and details in my accessories doesn’t detract from an otherwise simple outfit. Further, Longwings can much more easily be dressed up or down than a purely formal shoe like a whole cut or cap toe Oxford.
well said. I agree that a much shorter person is likely better suited with a plainer shoe. (Pun always intended.)
here in NYC you see everything. I've seen gents with jeans and oxford pulled off quite well. A lot of you have suggested brogues. Unfortunately I'm not a fan of the complexities and busyness the brogues bring when worn. I'm a fan of simple uncluttered design. Suede derbies might be appropriate. I also like the idea of leather chukka. I'm still trying to grasp the wholecut silhouette with jeans but I think it can be done. I'm still not conivned oxford and jeans can't be done, but I think it really depends on the jeans. This is a look that's not unpopular here by some.
I can almost view wholecut like lowtop chukka boots.
How about a hybrid like an Adelaide or wholecut with a medallion?
 

nikolau

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well said. I agree that a much shorter person is likely better suited with a plainer shoe. (Pun always intended.)

How about a hybrid like an Adelaide or wholecut with a medallion?
A hybrid like a wholecut with a medallion might actually look pretty good tomorrow but will the same be true in 3-10 years? I’m doubtful. Further, the brogue detailing on such a wholecut seems like a likely point of failure in the shoe after significant wear.
 

EZB

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A hybrid like a wholecut with a medallion might actually look pretty good tomorrow but will the same be true in 3-10 years? I’m doubtful. Further, the brogue detailing on such a wholecut seems like a likely point of failure in the shoe after significant wear.
Brogues don’t fail.....wtf
 

nikolau

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Brogues don’t fail.....wtf
On a wholecut wouldn’t a brogue literally be a hole punched all the way through the upper?? Otherwise it wouldn’t be a wholecut.
 

breakaway01

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At the OP’s price point I would avoid wholecuts. Because wholecuts use a larger (and thus more expensive) piece of leather, a $240 pair of wholecuts just won’t be made of good leather.
 

norcaltransplant

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A hybrid like a wholecut with a medallion might actually look pretty good tomorrow but will the same be true in 3-10 years? I’m doubtful. Further, the brogue detailing on such a wholecut seems like a likely point of failure in the shoe after significant wear.
This is just awful advice. The Crockett & Jones Weymouth has been around since before 2000. It was on the 337 last and now the current iteration is on the 373. The latter is more elongated. The brogue detailing is in the toe cap, and does not bend. I own a lot of shoes with toe medallions and the failure point is always the vamp.

IMO, wholecuts are a bit too dressy for jeans, even dark wash. I much prefer a country style shoe (derby, pebble grain, dainite sole, etc.) or even single or double monkstraps for jeans.
 

Chowkin

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On a wholecut wouldn’t a brogue literally be a hole punched all the way through the upper?? Otherwise it wouldn’t be a wholecut.
No it isn’t. A wholecut, while made from a single piece of leather, would still have a leather lining.
 

Chowkin

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IMO, wholecuts are a bit too dressy for jeans, even dark wash. I much prefer a country style shoe (derby, pebble grain, dainite sole, etc.) or even single or double monkstraps for jeans.
I admit that wholecuts are dressy but they still pair quite nicely with jeans:

22B96999-5ACE-4CA7-B80F-1532DBE0FA9A.png

Not that much different from a pair of Chelsea boots:
F74829C0-7F9D-443F-AED2-166757B8BBCD.png
 

mux8

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How about suede oxfords? Still too formal?
 

Phileas Fogg

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How about suede oxfords? Still too formal?
depends on the shoe. The suede definitely brings down the formal factor by a notch.

Why are you so locked in on oxfords? There are so many better options.
 

Lem87

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Why not wear a chelsea if you feel you need to over think it? Basically anything that slips on to your foot regardless of the style counts as casual. Maybe you're a closeted driving moc guy since you insist on casual shoes and not boots? That's what it sounds like to me..
 

mux8

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haha, maybe... Chelsea's feel so.... bleh. Nearly every other guy is wearing a chelsea these days. The elastic also don't interest me. Maybe it's time to try Jodhpur Boots?
 

Lem87

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haha, maybe... Chelsea's feel so.... bleh. Nearly every other guy is wearing a chelsea these days. The elastic also don't interest me. Maybe it's time to try Jodhpur Boots?
I'd say that depends on how flirty you are with your ankles.... I say that as a guy who has 9 wellingtons (4 engineers 5 western styles). I also *ahem!* have my first MTO in the form of a nice chunky chelsea due to arrive some time in the next 2 weeks. It has a fat assed welt and chunky soles along with a whiskey shell upper to go with it. Does detail no one is really going to see, really matter?
 
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mux8

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Well everyone keeps suggesting chelsea boots, but the GF doesn't like chelsea's on men and says they look feminine and boring :(. In any case, summer is coming up which is why I prompted the discussion for non-boot styles that work well with jeans.

I have ordered some medium brown suede oxfords and split-toe derby shoes, hopefully those are more acceptable with jeans.
 

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