New Member
United States
North Carolina
From my fading memory, penny loafers, deck shoes, desert boots. I don't know if there are Italian equivalents to those. I was just in Italy thirteen months ago but only noticed how few "tiny suits" I saw on humans; there were many in the windows in Milan, though.



United States
There’s something odd to my eye about wearing a polo shirt with desert boots or chukkas.

In fact, there’s something odd to me with wearing a polo shirt and dark jeans. But given the question, deck shoes or penny loafers. Perhaps even bit loafers


Super Member
United States
North Carolina
I only own one pair of jeans and generally wear my chukkas or penny loafers with them. A polo versus a button up shirt makes some difference as I would generally forgo the chukkas for loafers or NSTs. I wear various boots or NSTs when wearing a flannel shirt or work wear and jeans. My only pair of sneakers are worn to the gym or to take the garbage out.
With chinos and a polo I wear loafers or any derby/Blucher I own. I really like NSTs and often wear them casually but I know quite a few people here dislike them. I generally wear my deck shoes with shorts or very casual cut chinos, never with the jeans unless it's just a quick run to the store.
I've worn closed lace shoes with jeans and or chinos occasionally though I know it's frowned upon here (except by Shaver with chinos). Generally only the least formal version I own. I know there are also some in the crowd that say deck shoes only if you're standing on a deck. I tend to use mine as drivers for long trips as they have a good heel design for it.

Prof Ray

Starting Member
United States
The big issue, of course, is what color loafer, etc., to wear with jeans. My jeans are all dark wash, and I recently purchased a pair of sand-colored, suede loafers, thinking they would provide a nice summer-y accent to my go-to causal outfit in the warmer months, a linen shirt and jeans. Unfortunately, I do not like the way they look paired with the dark jeans. I'm either going to find a darker pair of loafers or find a pair of jeans I like in a lighter wash (or maybe just convince myself the stark contrast between the loafers and jeans is stylish!). I bring this up because it's likely to become an issue for the OP, as well.


Senior Member
United States
San Francisco
I agree with the suggestions for loafers, but believe deck shoes are meant only for boating.