Tom3

New Member
47
United States
North Carolina
Asheville
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.

Tom
 

SG_67

Connoisseur
15,067
United States
Illinois
Chicago
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
 

winghus

Super Member
1,023
United States
North Carolina
Greensboro
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
6
United States
Indiana
Indianapolis
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.
 

DG123

Senior Member
815
United States
California
San Francisco
I agree with the suggestions for loafers, but believe deck shoes are meant only for boating.