Wow. I realize Angie has spoken, but that is so different from how I perceive loafers, especially this style--which so makes me think of fall and plaid skirts. Maybe I'm more preppy-or hipster-than I thought.
I have only this summer embraced the look of flat loafers without socks as a summer item, even worn with dresses (and my stylish daughter pointed out how trendy I was being when she saw me doing it--as in, Mom, did you know that was trendy now, or did you just pull them out of the back of the closet?) I was very happy this worked because it allowed me to resurrect a pair of black patent loafers that were never comfortable with socks, despite, adding arch supports, yet feel great on with bare feet, go figure!
But I digress. I'm sure this is a trend that won't last, maybe even as long as till next summer. In a year or too this look (especially with dresses) will I think look as dated as 80s shoulders. But that loafer you highlighted is to me one of THE classic fall-and-winter shoes. I would wear it with black socks and black or tweed pants for pretty much every workday outfit I can picture myself wearing. For "me" time when I can be a bit more trendy, I would go big with argyle or even my black-and-white striped socks, with jeans or pants narrow and short enough that you couldn't miss the socks.
But then, that's me. I certainly skew more classic and menswear than Angie's look. And I have Canadian winters to deal with, which means I can't go sockless, and I don't want to ruin my floors by wearing my winter boots inside, so a quick slip-on when I go inside feels natural. (Ie I'd wear these like oxfords plus the convenience factor)
What would feel too preppy on me would be wearing it with knee socks and a tartan skirt (though heaven knows I'll be tempted) And I would do that with my stack-heeled loafers, sans the knee socks.
