Not sure what shoes to wear that hit the sweet spot between casual and dressed-up? Penny loafers might be your new go-to. Timeless, versatile, and effortlessly stylish, they can elevate just about any outfit, from jeans to suits.
But getting them right is key. From what they are, to how to style them for different occasions (yes, even with shorts), this guide will show you how to make penny loafers work for your wardrobe, without overthinking it.
What is a penny loafer? Penny loafers' history shows that they kicked off in the early 20th century. Ivy League students made them the go-to for that preppy, polished look. Since then, they’ve grown in popularity. They evolve just enough to stay fresh while keeping that timeless vibe.
Leather’s the classic choice. It’s tough, it shines, and it gets better with age. Black leather loafers are your ticket to looking sharp and professional, while brown ones bring a warmer, more laid-back feel. Leather penny loafers with shorts provide a classy look.
Suede loafers have a relaxed, almost velvety charm that’s perfect for kicking back. They add a little texture to your outfit, but watch out—they’re not fans of puddles. On a dry day, though, they’re pure gold.
Penny loafers aren’t stuck in the past. You’ll see them jazzed up with tassels for a fun twist or metal bits for some extra flair. These tweaks keep the classic shape alive while letting you express your style, whether you’re feeling playful or edgy.
Looking for penny loafer outfits tips? If you’re wondering how to style penny loafers, here are a few ideas:
Put casual penny loafers on with jeans and a t-shirt, and you’ve got a look that’s easy but still says you care. Jeans and penny loafers are a sure hit.
Match them with chinos and a button-down shirt for a clean, approachable vibe. Toss a blazer into the mix, and suddenly you’re ready for dinner or a casual office gig. It’s polished, but you won’t feel like you’re trying too hard.
Go for black leather, and they’ll work for semiformal spots like weddings or cocktail nights. They’re not as stiff as dress shoes, but they bring enough sleekness to keep you looking stylish without the fuss.
Under the theme ‘how to wear penny loafers’ is the key question: Can you wear socks with penny loafers? Stick to no-show ones for that stealth support, or pick thin, neutral socks that blend in. Either way, the loafers are the star of the show.
When choosing penny loafers, it’s all about selecting shoes with superior style, made from top-quality materials. Upscale Menswear offers dozens of the best men's penny loafers you’ll be excited to wear, including these distinctive choices:
Belvedere "Espada" Black/White Genuine Ostrich Quill Penny Loafer 02440
These exceptional quality ostrich skin shoes are handmade by one of the finest exotic shoe manufacturers, Belvedere. Everyone will wonder where you got these completely handcrafted and hand-stitched beauties!
Belvedere "Maurizio" Cognac Genuine Nappa Leather Hybrid Penny Loafer
Get one or more pairs of these quality handmade hybrid loafers created by one of the finest exotic shoe manufacturers, Belvedere. They’re completely handcrafted and hand-stitched, with a traction outsole and cushioned insole.
Mezlan "Parole" Bone Soft Textured Calfskin Leather Penny Loafer 21047
These soft-textured calfskin leather penny loafer shoes are handmade by one of the most celebrated exotic shoe manufacturers, Mezlan, which offers outstanding exotic skin shoes from Spain, completely handcrafted and hand-stitched.
Mezlan Cognac Genuine Calfskin Leather Penny Loafer E20243
These must-have genuine calfskin leather penny loafer shoes are handmade by celebrated exotic shoes manufacturer, Mezlan, which offers superior handcrafted and hand-stitched exotic skin shoes from Spain.
Lombardy Brown Genuine Crocodile / Leather Penny Loafer Shoes ZLA048207
Lombardy makes amazing exotic skin shoes. They are all made by hand. The insides are soft lambskin for comfort. The soles are leather and stitched by hand for good traction.
With so many styles, colors, and materials to choose from, you’ll need several pairs of penny loafers to add to your wardrobe. Upscale Menswear is your perfect source for all the quality brand penny loafers you want. Our easy-to-navigate website makes it simple to find and order your loafers so you’ll have them to pair with your favorite outfits.
Pick up all the penny loafers you love in the styles and colors you want at Upscale Menswear. Shop now for the ultimate selection of penny loafer styles!
1) Are penny loafers in style currently?
If you’ve searched “penny loafers men style,” you’ll find they’re a timeless classic with periodic fashion resurgences.
2) Can you wear penny loafers with a suit?
“Penny loafers with suit” is a theme people wonder about, and loafers pair excellently with suits for a sophisticated yet relaxed professional look.
3) Why are they called penny loafers?
Students in the 1930s inserted pennies or coins into the shoe's decorative slot for style.
4) Can you wear socks with penny loafers?
If you want to know what to wear with penny loafers, socks are okay! Dress socks or no-show socks work well with these shoes.
