Style

The Best Outfits to Wear with Penny Loafers

A pair that's worth pinchin' your pennies

We hear from guys all the time that they want to expand their footwear repertoire, but keep falling back on old standbys. And while there’s nothing wrong with a chukka boot or white sneaker, it’s good to switch it up from time to time, too. That’s why today we want to share how to wear penny loafers five different ways.

Penny loafers strike that retro-yet-timeless vibe that we all want more of in our wardrobe. Plus, these shoes are quite literally effortless (slip on! no laces!) and you can dress them up or down. Really, there isn’t any good reason not to add a pair in your shoe collection.

What’s a penny loafer, anyway?

Relatives of the penny loafer include plain loafers (usually made of leather), tuxedo loafers for black tie events, Italian loafers which have a metal strap across the top, and driving moccasins a more casual shoe, worn at home or driving a sports car with a beautiful model at your side (I think, anyway).

The penny iteration came to be in the 1930s. John Bass (of G.H. Bass…maybe you’ve heard of ’em?) decided to add a stylish strap to the basic loafer, creating a new look that he called “Weejuns.” The strap had a design looking like a pair of lips, and people would dress up their shoes by putting small items – like pennies – in the strap. Some would even use the penny at a pay phone for emergency phone calls home. Ha, pay phones…

Are they still stylish?

This isn’t your dad’s penny loafer…actually, it is, but it’s time you stopped thinking of it like that.

Given the penny loafer’s ability to look even more stylish sans socks, and also its throwback vibes, it’s time to get onboard with this footwear for the future. We’ve come up with five very different ways to wear this shoe, so you can see how versatile it truly is. Especially in the summer. If you can’t be sporting sandals, a penny loafer might just be your next best bet.

You can always mix it up with penny loafers that come in suede, or swap out the pennies in favor of some playful tassels.

Why penny loafers deserve a place in your wardrobe

While the penny won’t get you very far these days, the style has stood the test of time – and for good reason. The shoe is a great addition to your wardrobe – wear it instead of sneakers with jeans or khakis, or instead of a dress shoe with summer-weight suits. And of course, swap out the boat shoes to wear a penny loafer with shorts for a truly stylish summer look.

Don’t be precious with your loafers – just wear them like you know how good you look (because I know you do).

Below, outfit ideas for how to wear penny loafers five ways:

From work to play, you’ll find this throwback shoe is ready for anything your wardrobe can throw at it.

MONDAY

How to wear penny loafers to a job interview

Wear it well: Go sockless for the perfect summer suit style.

TUESDAY

How to wear penny loafers in a casual outfit

Wear it well: Roll your chinos and pass the guac. This look is cool and casual, and could easily be worn with sneakers…which is exactly why penny loafers make for a fun and unexpected statement.

WEDNESDAY

A penny loafers outfit for the office

Wear it well: Roll up your sleeves (here’s a primer if you need it) and get to work, in this office-appropriate look. Stick to no-show socks in the warm weather months for a little dress code-friendly ankle-flashing.

THURSDAY

How to wear penny loafers on a date

Wear it well: Cuff the chinos and be sure to offer your bomber jacket to your date if the AC gets too chilly.

FRIDAY

A penny loafers outfit idea for the clubhouse

Wear it well: Roll your short sleeves just so, while your penny loafers upgrade a shorts outfit for a perfect post-9 rounds beer with friends at the club.

Shop our favorites

The OG // G.H. Bass Larson Weejuns, $110
The suede option // M.Gemi, $275
The loafer-boat shoe hybrid // Cole Haan, $140

Looking for more ways to wear your favorites? We show you 5 ways to wear your chelsea bootswhite jeans, and denim jacket.