Loafers are back in a big way.
Don’t get me wrong—they’re never out of style. They’re classics, after all. But I’m seeing them in a lot of new contexts. Once upon a time, loafers weren’t workwear-friendly or even fashion-forward.
Not anymore.
So what does this mean for us loafer lovers? Are there wrong ways to style them? Is the classic smart casual context they were made for now considered old and musty?
To answer these questions and more, we’ve got 17 outfits here. And, of course, they represent a wide range of personal styles.
Table of Contents
17 Ways to Style Loafers: Outfit Inspiration
Casual But Dapper
Starting with something more traditional, this outfit works because of the smart cuts of each garment. His linen pants are relaxed, which matches his knit polo. However, every hem on the polo is cinched.
This balance of smart and casual is the most natural habitat for a loafer. Plus, the resort-ready color palette of the outfit allows him to wear white loafers, which can sometimes look too bold.
Workwear High-Low
How does one wear loafers with workwear and workwear-inspired pieces? Take a look at these guys. Here’s a style secret regarding building high-low combinations. You can create a suit-like silhouette using casual outfits, making the more formal pieces look at home.
In these cases, their collared work shirts have the same shape as a dress shirt, while the utility jackets serve as the suit jackets, silhouette-wise.
Updated ‘80s Banker
Combining big lapels with pinstripes can be a bold choice. However, it looks intentional if you lean hard into the look, as this gent does (just look at the contrast collar and club tie). Besides, oversized is in.
What brings this look into the present day is how the suit pants taper towards the ankle. The simple lines of his loafer match that clean look.
T-Shirt and Jeans
Another way to style loafers with casual outfits, particularly ones that incorporate classic workwear, is by going for bigger, chunkier models. This look gels together beautifully because the rubber soled, tassel loafers match the brawn of his denim pants. Meanwhile, he color-matches the shoes with his shirt. Props to him for the bold statement necklace too.
Cool Weather Textures and Layers
Who doesn’t love a layered fall-to-winter look? What this guy does so well is he pairs a lot of organic looking shades of brown and green, allowing him to sport black loafers and black socks without the neutrals competing with each other.
Also, he chooses a slick loafer that, tassels aside, are pretty minimal. This makes it another perfect balance of details and minimalism.
Trendy Athleisure
I never thought I’d see the day loafers could be worn with athleisure. It’s a trendy look for sure, but if that’s your thing, this outfit succeeds.
He’s able to pull the combination off because he sticks to literally two colors, creating a visual neatness. And, he throws on a trench coat, adding structure and a touch of formality to the silhouette.
Subtle Contrasts
What’s clever about this deceptively simple outfit is the small details that take it from standard to really attractive. The ring, watch, and dark loafers stand out against the all-neutral outfit, but not in a loud statement kind of way. The low dip of the unbuttoned shirt gives the outfit an on-holiday vibe, which he carries on with the socklessness.
Street Style
Don’t discount loafers if you have a more casual and chicly urban sense of style. He’s making loafers work in this outfit simply due to color matching. Who would’ve thought?
Even down to the details of his hat and watch, there are two colors going on here. The loafers are certainly a style contrast, but one that’s clearly well thought out.
Trend-Forward Yet Classy
Some people conflate structure and neat lines with a slim fit. This guy knows better. And again, just as the loafer represents a dressed-up and relaxed aesthetic, as does this outfit.
His shoulders are structured, but his pants are flowy. He also goes full tonal with the belt, pants, and shoes, which fully cinches the intentionality of the look.
Modern High and Low
Throwing a blazer over a t-shirt and jeans has been around since the ‘80s. I can’t think of a better shoe to complete that combination, but a loafer.
And despite his high-low approach, he still follows some important fundamental rules: The leather of the shoes is tonal with the leather of his belt, and the hardware on his shoes matches the buttons on his blazer.
Classic High and Low
Here’s a more traditional high-low approach, otherwise known as a broken suit. He has some fun with it, though, including going for an open double-breasted jacket, striped shirt, and purple socks. Still, the simple black loafers anchor the look, distracting from what some might consider broken rules.
Formal but Cozy
Full disclosure: This guy? He’s me. But here’s why I like this outfit. The cashmere turtleneck adds a relaxed factor that matches the vibe of the loafers. Even more, I go for suede shoes to really lean into that factor. Then, by going tonal with the suit pants and turtleneck, they match in a different way than the sweater and shoes do.
Stylish Color Blocking
Less is more in this combination, which is what makes it succeed. The camel coat adds structure, but this look works with or without it. By going for bit loafers, his shoes really pop and add that architecture that the coat also does.
Traditional Smart Casual—With Some Fun Pops
Here’s another traditional broken suit, but one that’s more formal because he’s wearing suit trousers instead of khakis. If you look closer, though, you’ll notice he’s having some fun with this standard template.
The light pink shirt is tonal-adjacent to the burgundy socks. And by going for a dark shade of burgundy, his black buckled loafers don’t look out of place.
Vertical Visuals
This simple shirt and trousers combination is all about the details. The vertical stripes on his shirt subtly match the pleats on his pants. Even more, the traditional waist placement of the pants is also in line with that verticality.
Despite being a simple two-piece outfit, it’s cleaner and sleeker because of these choices. And if you’re a man of more modest height, these are good strategies to put in your back pocket.
Fashionable Anti-Fashion
The confidence naturally imbued in this outfit really makes it ooze with cool factor. He pulls off this mix of anti-fashion trends (oversized top, white socks with black loafers, dad hat) because he chooses neutral colors and simple pieces. If he wore sneakers over loafers, it would better follow traditional style rules, but it also wouldn’t be “a look.”
Traditionally Dapper
And, of course, you can’t go wrong with simply wearing loafers the way they were meant to be worn. His white shirt and white pants have a vacation vibe, as does the fact he goes with browns over blacks. That being the case, this is the kind of outfit that begs you to go sockless.
Key Rules for Styling an Outfit with Loafers
Consider The Best Type of Loafer for Your Outfit
Remember how that chunky tassel loafer looked great with the t-shirt and jeans? Or how all of the more formal outfits above incorporate slimmer, more minimal loafers? Not all loafers are made alike, and there are many different types. Make sure your shoes match the aesthetic of your outfit.
Keep The Setting and Occasion in Mind
Related to choosing the right kind of loafer for your outfit, keep in mind the level of formality and the necessary functions you might need. If you’re going to a beach wedding, you might want rubber outsoles over leather ones.
Meanwhile, an opera pump really only goes with a tuxedo. When in doubt, though, go for the penny loafer. It’s definitely the most versatile model—not too stuffy and not too casual.
Match Your Loafers to Your Socks
There are different ways to approach sock color when you’re wearing loafers, which we detail here. However, the most traditional and safest approach when it comes to avoiding faux pas, is matching your loafers to your socks.
By wearing black loafers with black socks, you create an extension of the shoe, creating aesthetic cohesion.
Or Go Sockless (When it’s Acceptable)
Yes, you can go sockless with your loafers (as a few of the outfits above exemplify). However, it’s definitely a more casual look that isn’t always appropriate in more formal dress codes, so if you’re wearing loafers with a suit, you might want to ignore this part.
But there’s a category of formal that I like to call “cozy formal”—think velvet details, shawl collars that look like smoking jacket collars, and slipper shoes. In these cases, going sockless might be okay. However, in formal venues or events, don’t take risks if you aren’t sure.
The Versatility of the Humble Loafer
When it comes to styling loafers, What takes me aback the most is how you can make it work with certain athleisure pieces.
That may go in and out of style, and I’m sure it will, but it’s a testament to the loafer’s adaptability to trends and classics.
I personally prefer to wear them traditionally, no different than the way my dad and granddad wear their loafers. But of course, you do you.
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