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Since the thread I started about the "suitability" of wearing a OCBD with a suit despite the objection of many fashion writers and menswear "experts" created a lot of opinions...let me throw out an even more controversial combination. Penny Loafers and suits? Not just the Alden LHS variety, or the full strap sleeker model with a more pointed toe...but any well crafted, good looking, well cared for quality penny loafer. Some consider this anathema...but I was intrigued when reading a book on men's fashion when the author mentioned a well known executive in NYC fashion circles who made it a personal fashion statement to always wear well polished black penny loafers with his impeccable tailor made charcoal grey suits. Forget the always wear lace ups with a suit...too many well dressed men wear tassel, bit, or full strap loafers with suits for that ole bromide to hold water except in the most formal setting. But I admit to being somewhat conflicted when it comes to penny loafers and suits. What say you?
 

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I've worn Alden 986s with a tan poplin suit. I've worn Alden for BB black shell cordovan loafers with a navy poplin suit. That's as far as I've gone, and I didn't feel quite right either time. I'd never wear Weejuns with a suit of any sort.

Whatever floats your boat, though, and you'll likely receive plenty of support here for your proposition (along with a request or two to check the archives).
 

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I guess my take on this is that, unlike OCBDs and tassels -- which obviously go well with a suit (look at Squire's "curriculum" thread for inspiration) -- pairing penny loafers and a suit is bit of a stretch. I'd say that it is acceptable with a more casual suit, such as poplin (as others have mentioned) or maybe seersucker.
 

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I see it (and worse) all the time in court and elsewhere, but I'll not do it.

That's why I have lace-up suit shoes (AE Byron in burg. and black) - I like to wear them with when I wear suits - otherwise, they would not get worn.

minor disclaimer: I would wear my calf tassel loafers with suits in a less formal setting (i.e. wedding) as well.
 

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I've done it.

I've worn penny loafers with a suit, but it was a poplin number. Seems as though my father does wear loafers of some sort with suits as well. (He's always been a Weejun wearer as long as I can remember.)
 

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I think a pair of penny loafers would work great with a poplin suit, followed by seersucker.

I think you could get away with pairing them with worsted wool, but I'd choose lace up oxfords first or tassel loafers second before pairing penny loafers with this kind of suit, and it would have to be a deluxe model like a shell LHS or another well-cared for option.
 

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A "dressy" penny loafer like the Alden LHS can work (IMO) with a suit, although it's definitely a casual look more appropriate for less formal-looking suiting fabrics (e.g., the aforementioned poplins). The typical Bass Weejun, however, is a no-no.
 

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I do it on days that I have traveled to give a lecture and then am going to the airport to come back. I don't love the concept, but my 986's are often the best pair of shoes in the room, and it makes going through security much easier.

I though about wearing bals to the lecture then changing on the way to the airport, but vanity is not worth the hassle.
 
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