nikolau
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As the rules go, the simpler the shoe, the more formal it is.
For example, these wholecut oxfords are considered to be very formal shoes, suitable for daytime and evening formalwear (morning coat or blacktie, for example):
(87 AE Dover)
The next level down, on the formality scale, would be plain-toed oxfords:
(Vintage Violation: 2015 AE Carlyle)
Then captoe’s and partially brogues captoe’s:
(88 Florsheim Penfield)
Finally you get to fully brogued captoes and wingtips:
(1995 AE Clifton)
(80’s Hanover LB Sheppard LWB’s)
A brogued wingtip, especially a blucher, is going to be at the informal end of the dress shoe spectrum (as they’re historically rooted in “country” shoes.
Which brings us to the weird outliers: the PTB and the Saddle Oxford (often just called a saddle shoe). They’re technically plain toed shoes, so they should be considered more formal than their captoe and and wingtip brethren, yet both are considered, historically, to be less than formal shoes. In the case of the saddle, it’s due to its origins as a “sporting” shoe, while the PTB, by nature of being a blucher, was considered fairly informal. Ultimately, they tend to have a similar profiles (for example the AE Shelton and Leeds are built on the same 511 last), and have somewhat fallen into the same category of formality:
(~1958 City Club PTB)
(Vintage Violation: 2011 AE Shelton)
That being said, the Saddle is one of my go to shoe styles that I wear with everything from jeans to 3-piece suits; they’re incredibly versatile. While I’m not a huge PTB fan, I think they fill exactly the same niche: they’re remarkably versatile, crossing the boundary between faux-formality (due to the plain toe) and informality very easily. Certainly more so than say the LWB, which always looks like a bit like an affectation when worn informally - though I wear LWB’s habitually with informal clothing, precisely because they’re an affectation in that context.
I think a key take away here could be that the more decorative detail there is on a pair of shoes, the less appropriate it happens to be for formal wear. For example, a mirror shined black chelsea boot or well polished cap toe oxford without any brogue detailing would be perfectly appropriate for black tie, even in Europe.
All that said, it happens to be a uniquely American thing that one can wear Alden or Florsheim longwings for practically any occasion and with practically any outfit and get away with it (depending on the choice of material). Personally, I like to think it’s part of the zeitgeist of this country that one can wear big clunky shoes for all occasions — just like one can drive a massive truck throughout a lifetime of urban commuting and drive-through-jamba-juice experiences. In a more reasonable world the drive through Jamba Juice would not accommodate an F150. It’s extraordinary, and I imagine longwings are not appropriate office/wedding/funeral wear in any other country. I, for one, am not complaining.
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