Loafers have been incredibly trendy lately, picking up a lot of steam in the world of men's fashion. I'm seeing lug-sole loafers and chunky loafers styled in tons of different outfits, but one of my favorite styles has always been the classic penny loafer.
Penny loafers are sleek, elegant, and incredibly versatile—they can be dressed up or down, making them a worthwhile investment. That’s why I wanted to round up some of my favorite penny loafers so you can invest yourself. Enjoy!
1. The Loafer | Amberjack
Loving the @wearamberjack suede loafers!
— The Guy’s List (@TheGuysList) March 9, 2025
Get them here ⬇️https://t.co/hvSTSr5KH4 pic.twitter.com/317gGqHgmv
First up, I had to go with The Loafer from Amberjack. This is one of my go-to pairs for summer, which will be here before you know it. I absolutely love the Tundra color—a light beige that pairs perfectly with chinos, jeans, or even shorts for a sharp yet relaxed summer look.
But the best part? These loafers are extremely comfortable, making them perfect for long days out and about. If you value comfort as much as style, you’ll love these. Plus, at $179, they’re an affordable pick for the quality you’re getting. $179 at Amberjack
2. Levanto | KOIO
Next up, I have to give a nod to the Levanto Loafer from KOIO. These are the definitions of elegance and premium craftsmanship. Made in Italy, you’re getting a finely handcrafted shoe that reflects true luxury—and the price tag confirms it. But trust me, these are worth the investment. Not only do they look incredible, but they’re built to last, making them a staple in any refined wardrobe. Available in three colorways, you’ll have no trouble finding a pair that suits your style. Plus, they’re designed for effortless wear—easy to slip on and off while delivering exceptional comfort alongside their luxurious aesthetic. $295 at KOIO
3. Cohen Loafers | Beckett Simonon
Next on my list is the Leather Cohen from Beckett Simonon. Beckett Simonon has a ton of great shoes—from boots to sneakers to loafers. All of their shoes are made to order, so you'll need to wait a bit, but the quality and craftsmanship are worth it.
A light brown pair is a classic choice, and these are my favorite light brown loafers that I wear all the time for weddings. They pair perfectly with blue suits or even casual jeans fits.
Don’t miss this one! Shop now for $219 at Beckett Simonon.
4. Thursday Boot | Lincoln
If you're looking for a classic formal loafer, check out the Thursday Boots Lincoln Loafer. The mahogany colorway is an absolute classic, offering a rich dark brown shade that’s perfect for formal events or any time you want to dress it up. I wear it for weddings and business meetings.
You’ll love this one because it’s a great-looking shoe for just $168. Just a heads-up—it runs a bit narrow, so keep in mind that this is a sleeker loafer, not a chunky one. $168 at Thursday Boot Co
That’s it! With these four-penny loafers, you’ll have plenty of options to step up your style this year. I’d recommend getting one casual suede pair for summer fits and one formal pair for weddings and business meetings. With that combo, you’ll be ready to handle any occasion that comes your way—while looking fly and stylish as always.
Follow me on IG @joe_sanfilippo for more style tips and advice—hit me up!