How to wear it: Sleek Penny Loafers in Summer

Joseph Abboud “Jared” Slip-On Penny Loafer – $89.95

The sleek penny loafer is the perfect warm-weather shoe for guys who like to dress up a bit, but still want to embrace the relaxed vibe spring and summer bring. The shape and leather uppers are like a trim dress shoe, but they loose the laces. The elongated silhouette & slim sole is similar to most monk straps, but there’s no flash from buckles. And that higher reaching vamp & tapered toe box keeps them away from the more casual boat shoe/weejun loafer look.

They’re inoffensive but still confident. They look great when worn sockless. And they go with everything from jeans to loafers. Here’s a few examples of how to pull off putting on a pair (or two) of this highly versatile style of shoe:

 

With a blue unstructured sportcoat and light pants

Right in the wheelhouse. Instead of  a dark navy blazer, something more true-blue. Instead of yellowish-khakis, a grey oxford cloth pant. The warm tones of the shoes really jump against that cool-toned backdrop, and you avoid the yacht-club look. Preppy but not barf-inducing.

 

With a mid-gray suit

You absolutely can go monochrome in warm weather. Skip the socks, keep the shirt collar open, and as long as your suit isn’t a super dark charcoal (but instead something in the middle) then you’ll be just fine. Incredibly clean.

 

With jeans and a light sportcoat or blazer

An easy way to still get some use out of your favorite jeans as the weather starts to heat up. As long as it’s not sweltering out (the sun has gone down), dark denim + a lightly structured, lighter shade sportcoat should go great together. It flips and updates the old blue-blazer + light chinos outfit the Thurston Howell crowd knows so well. Just make sure there’s minimal lining to your jacket. That option from J. Crew Factory has a totally unlined back w/ acetate lined sleeves.

 

White & Black, light & casual (but still put together)

This is the one that most guys are going to push-back on and be scared to try. White & off white and… black? Not brown? Don’t knock it ’till you’ve tried it. If you’ve got a favorite watch that happens to be on a black strap, this would be a decent way to wear it more often in warm weather. Plus, those Abboud loafers don’t come out of the box with the highest of shine. They’re dressed up in shape, but lean somewhat matte in finish. That’ll help them look more casual.

ABOUT THE SHOES: DSW’s Joseph Abboud Jared loafer lists at $89.95, goes on sale from time to time, & ships free if you join their email list and use code SHIPR. Fit is true to size. 10.5 fits like a 10.5 D. Leather quality is decent for the price. Nice and pliable. Made in China. Available in black or cognac. Want to invest in something higher quality? Try Jack Eriwn’s blake-construction Abe loafer.

Joe

Recent Posts

Monday Men’s Sales Tripod – Brooks Brothers Pants, Timex flagships, & more

End of summer clearances + new arrival sale reluctance = stuck between seasons.

5 hours ago

Steal Alert: Banana Republic Factory 64% off most 48 hour sale

Sunday & Monday only. Shawl collar sweaters. Quilted jackets. Lots of new fall arrivals. BRF…

1 day ago

Newness News: J. Crew’s Fall 2026 Collection has arrived

But will any of it go on significant sale anytime soon? Attempted analysis of sale…

5 days ago

10 Style Changes to make for Fall

The stylistic shifts to make as autumn accelerates.

5 days ago

1 Sale (weekend), 5 Outfits: All the Labor Day Sales

"Who are you wearing??" ... "The Sale section. All of them."

1 week ago