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Discussion Starter · #1 ·
I'm considering getting brown full brogue wingtip oxfords for my first pair of dress shoes. I already have two pairs of chukka boots but I don't believe these count as dress shoes.

I know that usually black cap toe oxfords are recommended for a first pair, but let me explain my situation. I live in an ultra casual country, where the average man wears a suit once in his life: to his own wedding, and it's not a requirement so less and less men are doing it. Because of this, I started considering other options for dress shoes. I'm looking for a pair that would work in casual situations for now. The only times I would want to dress up is to weddings, and I rarely go to these. Even then, the casual nature of my country makes even chukka boots completely appropriate for such occasions. Actually I was even told by a co-worker that he would wear my boots only to weddings (but to me they're strictly casual).

So, would wingtips be a good choice for a first pair of casual dress shoes? If not, what else should I look into?
 

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Sounds like you have already thought this one out. A brown brogue will look fine with a blue suit as well as jeans and chinos. A cap-toe doesn't look right as a casual shoe. I would also suggest a blucher or derby instead of an oxford.
 

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Discussion Starter · #4 ·
Sounds like you have already thought this one out. A brown brogue will look fine with a blue suit as well as jeans and chinos. A cap-toe doesn't look right as a casual shoe. I would also suggest a blucher or derby instead of an oxford.
Thanks for the reply! So did I make the right decision? Why would take a derby over oxfords? I'll be honest, I'm not the biggest fan of derbies, especially with broguing. Doesn't the broguing make the oxfords casual enough?
 

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Hi Andy! Thanks for replying.

Well, I'm aware of this fact. More casual shoes is exactly what I need, which is why I'm attracted to wingtips.
Not to speak for paxonus, but perhaps he had in mind your emphasis on the more casual. A derby is innately less dressy than an oxford. But if you prefer an oxford, there's no reason that shouldn't be your choice.

It's very difficult to offer advice between cultures where many norms will be different. And certainly if you lived in one where men often wore sophisticated dark suits, a black cap toe oxford might be a best choice. But I agree with paxonus that you seem to have thought this out well, and as best as I can understand your circumstances, it would seem like a reasonable choice.
 

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Pics of your Chukkas? In this modern slobbish world, smooth leather chukkas count as dress shoe-boots in most offices.

In your your casual world I think wingtip oxfords would be a good choice. You also might want to look into something like a medallioned wholecut or medallioned toe shoe with limited brouguing.

Here is a sleek example -
 

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Pics of your Chukkas? In this modern slobbish world, smooth leather chukkas count as dress shoe-boots in most offices.

In your your casual world I think wingtip oxfords would be a good choice. You also might want to look into something like a medallioned wholecut or medallioned toe shoe with limited brouguing.

Here is a sleek example -
Weymouth? Yes - that is a nice shoe indeed.
 

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Discussion Starter · #16 ·
Pics of your Chukkas? In this modern slobbish world, smooth leather chukkas count as dress shoe-boots in most offices.

In your your casual world I think wingtip oxfords would be a good choice. You also might want to look into something like a medallioned wholecut or medallioned toe shoe with limited brouguing.

Here is a sleek example -
The boots I have are like these (I think it's also the same model):

https://media.sivvi.com/media/catal...f139433887a97daa66f/a/l/aldo_47199280_sa2.jpg

Aren't wholecut the most formal though? How would I be able to incorporate such shoes into my wardrobe, considering my ultra casual environment?
 

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Discussion Starter · #17 ·
Know what shoe design makes it casual or formal.
Know what the local perceives as casual or formal.
Determine how much you want to rebel against or follow the mainstream.
Pull the trigger (not literally)!
I have spent quite some time reading about dress shoes, and now I can tell pretty easily how casual or formal a pair is, thus why I'm considering wingtips. The local is going to perceive them as super formal, most likely. But I don't care much to follow whatever they're doing, as my only choice for casual shoes then would be sneakers at best, and sandals/slippers at worst. I've been wearing casual leather boots for so long now that I don't feel comfortable wearing sneakers outside the gym anymore. Casual dress shoes are to me the next logical step. I'm trying to convince myself that sneakers are cool for casual wear, but I'm failing at this very miserably.
 

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The boots I have are like these (I think it's also the same model):

https://media.sivvi.com/media/catal...f139433887a97daa66f/a/l/aldo_47199280_sa2.jpg

Aren't wholecut the most formal though? How would I be able to incorporate such shoes into my wardrobe, considering my ultra casual environment?
I like those boots. I think they can be very versatile and short of a dark, sober suit, will go with just about anything.

Given what you've said about your regular attire, I don't think wholecuts are necessary. A single pair of black captoe oxfords will suffice for those rare occasions that you will wear a suit.
 

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Discussion Starter · #19 ·
I like those boots. I think they can be very versatile and short of a dark, sober suit, will go with just about anything.

Given what you've said about your regular attire, I don't think wholecuts are necessary. A single pair of black captoe oxfords will suffice for those rare occasions that you will wear a suit.
It's surprising to know that chukka boots are so versatile they can even be worn with a suit! I wear them with dark wash jeans and chinos. They look incredible with jeans (the right type of course).

Well, those occasions in my case are so rare they will most likely happen only once in my life, which is at my own wedding. Maybe at my brother's wedding too but it's not a requirement. I'm not sure if it's wise to still consider black cap toe oxfords when I'll a wear a suit only once or twice my entire life.
 

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It's surprising to know that chukka boots are so versatile they can even be worn with a suit! I wear them with dark wash jeans and chinos. They look incredible with jeans (the right type of course).

Well, those occasions in my case are so rare they will most likely happen only once in my life, which is at my own wedding. Maybe at my brother's wedding too but it's not a requirement.
Perhaps a cotton poplin suit, but otherwise the chukka would look out of place with a suit. There are some boots that can be worn with a suit, but not a chukka.
 
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