How to Wear Penny Loafers: A Man’s Style Guide

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We hear it from men all the time. I’m looking to expand my footwear repertoire, but I keep falling back to my old standbys.

Of course, chukka boots and white sneakers are fine, but it’s nice to change them once in a while!

Input: penny loafers.

Penny loafers have a retro yet timeless feel and look great on men.

Plus, these shoes are literally effortless (Slip on! No string!), can be dressed up or down.It’s true, there’s no good reason No Add a pair to your shoe collection.

That’s why today we’re sharing why Team SG likes men in loafers and how to wear penny loafers with more outfits.

Keep reading to discover:

What are penny loafers, anyway?

And why are they called penny loafers?

Base Wee Jean Penny Loafers

Relatives of penny loafers include plain loafers (usually leather), tuxedo loafers (perfect for black tie events), Italian loafers with metal straps on top, and driving moccasins (worn at home or on the road). , more casual shoes). A sports car from a European country.

The Penny iteration took place in the 1930s. John Bass (The GH Bass…you may have heard of it.) decided to add stylish straps to basic loafers, creating a new look he called “Weejuns.”

The strap had a lip-like design, and people used to dress up their shoes by putting small items such as pennies in the strap.

Some people use pennies on payphones to make emergency calls to their homes.

(Note Gen Z: Payphones are what millennials used to let their parents know they were ready to be picked up at the mall.)

Are penny loafers stylish?

penny loafers

This ain’t your dad’s penny loafers…it really is, but it’s time to stop thinking that way.

Given the penny loafer’s ability to look even more stylish without socks, and its retro feel, it’s time to step into this footwear for the future.

This year, we also introduced a rag sole style that puts a new twist on the timeless shoe. This one is more trendy, so if classic style is more “you,” feel free to go for it.

Always ready to mix with incoming penny loafers suedeor trade pennies for something playful tassel.

Why penny loafers are a wardrobe essential

These days, pennies can’t take you far, but the style has stood the test of time — and for good reason.

Pair with jeans and khakis instead of sneakers, or with a summer suit instead of dress shoes, it’s the perfect addition to your wardrobe. And of course, swap out your boat shoes for penny loafers and shorts for a truly stylish summer look.

Don’t value your loafers. Wear it like you know how good you look (because I know you do).

Check out what to wear with penny loafers below.

From work to play, these retro shoes are ready for anything in your wardrobe.

Monday
work, office, meeting

How to wear penny loafers to a job interview

Wear well: Can I wear loafers with my suit? of course. Create the perfect summer suit style without wearing socks.

Tuesday
tacotuesday, casual outfit with penny loafers

How to wear penny loafers for a casual outfit

Wear well: Roll your chinos and pass the guacamole. This look is cool, casual, and easy to wear with sneakers…which is why penny loafers make a fun and unexpected statement.

Wednesday
workdaywednesday, penny loafer outfit ideas, how to wear penny loafers

penny loafers for the office

Wear well: Roll up your sleeves (check out this primer if you want one) and get to work in this office-worthy look.

Wear no-show socks in warmer months to match your dress code and expose your ankles.

Thursday
theaterthday, how to wear penny loafers, penny loafer outfit ideas

How to wear penny loafers on a date

Wear well: Tighten the cuffs of your jeans with penny loafers, and if the air conditioning is too cold, offer your date a bomber jacket.

Friday
fridayfun, how to wear penny loafers

penny loafer ideas for clubhouse

Wear well: Roll up your short sleeves and upgrade your shorts look with penny loafers for a perfect beer after nine rounds at the club with friends.

Shop #SGapproved loafers

Looking for more ways to wear your favorite?

Check out our outfit ideas for Chelsea boots, Henley shirts, and chore coats.

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