Hey Reagan, thanks for the question and good eye! Shorts + a dress shirt or sport shirt with the sleeves rolled up is sort of our go-to off-duty summer (and Indian summer) look. So the dog days of August are sort of a perfect time to tackle this.
Now some might immediately balk at wearing long sleeves in the heat, but there are tons of advantages! You can adjust the length for your tan lines… you can proportion your sleeves to your shorts length… you can even unroll for better bug coverage… hey, real problems! A little inside baseball - I prefer the ones we sell as dress shirts (vs sport shirts), and I throw one on after I've worn it once to the office. And that 2-for-1 means there's less stuff you need in your closet. But sport shirts are great for this, too.
Reagan was right
Anyway, as long as you stick to our well-documented "let your colors be from nature" and "only have 1 lead singer" rules, this simple shirt + shorts combo guarantees you'll be a little more refined and a little less "stock dad" at pretty much any casual summer get together.
But to get to your actual question. What do you do for shoes? I'm immediately looking for a few options that cover casual-to-formal on the summer spectrum, and then add the belt at the end based on those.
To start, I'd want one casual shoe option - a wholecut or slip-on sneaker, or classic tennis shoe (Onitsuka Tigers, anyone?) - for your backyards or baseball games. I'd have to say the most appropriate one for this very moment, would be the Sand Suede Lace-up wholecut sneakers. It's the perfect transition for Fall. (Although speaking of backyards, old Blundstones or chukkas are my go-tos with shorts for yard work.) And all of these could be worn beltless, but also with one of our new woven elastic belts, a D-ring belt, a polo belt, an African beaded belt, or a quiet 1" leather one, like a bridle with a spur buckle.
Second, I'd want a shoe option that's super versatile - a camp moccasin or driving moc or blucher - that can blend in almost anywhere, from lake outings to brunch. There's probably not a better option right now than the Slip-On Espadrille Moccasins. They come in a few different Indian summer/Fall colors (Sage!) with the option of a crepe sole or a rubber sole. ANY of these shoes are gonna go with most of the casual belts I just rattled off above, but can get dressed up with leather or suede or even a matte exotic. Just make sure the shoes/belt colors are on the same team.
And finally, I'd want one shoe option that could be worn somewhere a little nicer, like an afternoon cocktail party, or a dinner out on a patio, or a visit to the club. For that I'm going with a tassel loafer or leather penny loafer. And I'm going to pair it with a belt that will look equally discreet and refined... bridle leather, pull-up, shark, alligator, maybe swap in a brass or sterling plaque for a little added touch. You get the picture.
And I'll leave you with one more idea. I love working on Saturdays so I'm basically in jacket-and-tie 6 days a week, so when Sundays roll around, I'm by the pool. This philosophy also applies there – and it makes a great upgrade to the polo or a t-shirt. Just swap out the shorts for swim trunks and button what you want.
Anyway, I hope that helps you identify a few that'll cover some ground and fit in with your lifestyle. Just don't think too much about it, and don't be afraid to keep it going through early fall.