Matt S

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Those a great casual shoes. You could dress them down with chinos and a polo or dress them up with heavy tweeds.
 

Woofa

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I played this game some time ago with myself and made the determination that I could not imagine a shoe (at an price,) which would be casual enough to pair with jeans and yet formal enough to pair with a suit. In my opinion you have to sacrifice somewhere to make this work and below $300 really limits options as you cannot use most of the AE's.

My entry would be the Loake Strand Semi Brogue in Burgundy calf. On the Herring website currently for $248.
 

twoinhandknot

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Yeah, a wingtip brogue is the closest you'll get. I would wear those with anything from khakis to a suit. Some would say penny loafers, as well.
 

Buffalo

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Very nice as I am a great fan of longwings which I wear with casual clothes as well as evryday suits.
 

SG_67

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I think those are great. When I think of versatility, I think chukka boot, but those are fine.
 

StephenRG

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I played this game some time ago with myself and made the determination that I could not imagine a shoe (at an price,) which would be casual enough to pair with jeans and yet formal enough to pair with a suit.
I respectfully differ - I think that a burgundy/oxblood monk strap can do both. Consider A-E's Warwick (now on sale for $247):



But YMMV. (I find the Warwick a little too blobby for my taste, but it makes the general point, I think.)
 

medhat

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I'm presuming this is a rhetorical question, "if you had $300 and could only have ONE pair of shoes...". For that budget I think I could easily (and more appropriately, IMO) get enough shoes to cover my entire life's routine. Actually, it'd be kinda a fun intellectual challenge.
 

Flanderian

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The OP's shoe is a very handsome and high quality shoe for any who enjoy that style. For myself, I'd find it too formal to wear with khakis, though that's personal preference, more than disagreement, and frankly, my same preference tends away from heavy brogues accept as dedicated country shoes.

I've got a major hankering for the shoe below, which I think can span duty from khakis to suits, although it's around $345 after the AAAC discount.
 

Woofa

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I respectfully differ - I think that a burgundy/oxblood monk strap can do both. Consider A-E's Warwick (now on sale for $247):

Yeah, I can buy that argument without too much issue.
As someone new to higher end footwear (last few years here on AAAC,) I have struggled with Monk's placement in my hierarchy. I know that they tend to be accepted as formal enough for a suit but I have not seen many I think work as well as laced shoes with a suit. I have been unable to commit to a single or double monk and currently find myself liking an in between model like the EG Audley.
On the flip side, I am also not a big fan of shiney, leather shoes with jeans. (Please understand that I am not part of the dark jeans world but rather 501's.)
In my opinion, jeans are better paired with:
1. a suede shoe/boot (like the Alden chukka boot in suede);
2. a highly brogued shoe/boot (like a Tricker's Bourton);or
3. a matte finished shoe/boot with no luster (like a 1000 Mile Boot.)

Again, could the original op's choice be worn with a suit? Yes.
Would most people even notice? No
Would this be more dressy than many? Yes
Would it be a great choice for most business wear? I believe the combination of blutcher + ornamentation and color (although it looks to be a dark enough brown, better a burgundy) makes me think there are better options.

Of course just a few years ago I could not have imagined wearing Monks and today I actually find myself thinking that leather and suede Galways might be a nice purchase. Who knows what I may like in a few years? (Those Button boots Momsdoc is ordering don't look half bad!)
 
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