How to Wear Loafers with Jeans According to Menswear Experts

Loafers can feel pretty smart and jeans are pretty casual, so you might be wondering, ‘Can I wear loafers with jeans?’ The simple answer is yes.

The beauty of loafers lies in their versatility: the same pair can work just as well with a sharp suit as with jeans and a t-shirt. (I know, because I’ve worn them both ways.) In either case, the loafer look holds up.

That said, proportions matter: baggy jeans and oversized tees clash with the refined silhouette of a sleek, almond-toed calfskin loafer. But slim-fit jeans and a tailored shirt? That pairing complements that type of loafer perfectly.

To provide you with extra perspective I interviewed Gen Z tailor and YouTuber Alejandro Jomar, and your author is millennial shoemaker Justin FitzPatrick. We’ll look at different jeans, different loafers, and different outfits to make sure you’re confident with your jeans and loafers combinations.

Are Loafers Casual?

• Smooth leather loafers with a heel block, sleeker silhouette, and almond-shaped toe are dressier
• Suede loafers with a rounder and/or wider toe are more casual
• Black leather is more formal than brown leather which more formal than suede
• Traditionally, loafers were always more casual than boots, but today’s “rules” are blurry

Jeans are undeniably casual. So, are loafers casual? Yes, and no.

Many loafers can complement casual outfits, but the average loafer in the United States, especially when made with a smooth leather upper and a leather sole, is thought of as a dress shoe — or at least, a shoe that can be worn with a tie if you so choose.

The loafer is how guys stay refined in an increasingly casual world.

“It really depends on the type of loafer, the style, the leather, and the little details,” says Alejandro. “Suede penny loafers are way more casual than black calfskin loafers. They all vary in formality — some loafers can work great in both a business casual setting and the most casual of casual settings. For my money, the tassel loafer is the pick when you want one that can pull double duty as casual or dressy.”

Casual loafers combine suede uppers and rounder, roomier toe boxes. Dressier loafers are typified by almond shaped toes and smooth leather, but you can still dress them down.

As menswear continues to trend more casual, the traditional “dress loafer” is starting to replace the Oxford as the go-to dress shoe. Many guys now wear loafers casually with jeans or chinos as a way to stay sharp without going full formal. In other words: today, the loafer has come to occupy the middle ground between dressy and casual.

The loafer has evolved into an everything shoe. That shift is real. I sold more loafers than boots last season. It didn’t make sense at first, until I realized: the loafer is how guys stay refined in an increasingly casual world.

What Are the Best Loafer Styles to Wear With Jeans?

• Casual = roomy toe, lighter leather
• Dressy = tapered toe, darker leather

Since jeans can be torn and baggy or slim and smart, different kinds of loafers will work best for the way you intend to wear them.

Casual Loafers for Jeans

• Suede loafers in lighter colors are the easiest to dress down
• Any loafer with a chunky sole is best worn casually with jeans or chinos
• Loafers with rounder, roomier toe boxes and suede uppers can be worn casually with jeans

The most casual loafers are the chunky ones with commando soles, often styled with baggier jeans. They aren’t meant for suits and are usually preferred by younger folks who want something that’s unambiguously casual – meaning chunky loafers aren’t versatile, but they might be just what you want. In fact, they come as close to the feel of a sneaker as you can get with this “dress shoe”.

Traditional styles like Alden Tassel Loafers or Grant Stone’s Traveler Penny Loafer, especially in brown suede with a roomy toe box, are also on the casual end of the spectrum. Many of Grant Stone’s come in rugged leathers like Kudu, Waxy Commander Suede, or oily Chromexcel leather — all are excellent options for denim.

Casual loafers can be worn with chinos and they can go business casual, but never with a full suit. Stridewise Editor-in-Chief, Nick English, often pairs them with jeans and a t-shirt for a laid-back, effortless look.

Dressy Loafers and Jeans

• Dressy loafers are tapered at the toe and made of smooth, dark leather; they can be worn with jeans if they’re also dark and tapered
• Black leather loafers with baggy or overly long jeans rarely work

At the dressier end, you’ve got sleek loafers with almond toes in materials like black calfskin. These are harder to pair with jeans, but not impossible. The key is tailoring — these loafers demand slim, properly cut jeans. The hem should sit right at the top of the shoe, no cuffed jeans here.

Black leather loafers with baggy or overly long jeans rarely work. (Alejandro’s doing it above, but he deliberately breaks these “rules” — which can be done, but it takes more thought than the average guy wants to put into his outfits!)

As loafers get more formal, your jeans need to match in dressiness. Loose jeans and a casual top call for wider, more casual loafers: something like a wide-toe penny loafer in suede. If you’re wearing slimmer jeans in a smart casual fit with a button-up shirt, you have more options. Sleeker loafers, like a chiseled-toe penny or a butterfly strap loafer, can look sharp here.

Tassel Loafers are the Most Versatile Loafers

And if you want just one loafer that does it all? Go for tassel loafers. The tassel is playful enough for casual wear, but still refined enough for suits. It’s a classic style that bridges the gap between casual and formal, making it one of the most versatile loafers you can own.

“I agree that the tassel loafer is the most versatile loafer,” says Alejandro. “If you’re gonna get one loafer and want to wear it business casual and with jeans, get a smooth brown tassel loafer like J. FitzPatrick’s Haller. It’s the easiest to match with the widest variety of outfits.”

The tassel is a safe bet for fitting all types of styles, from casual to dress and everything in between. It can be playful, but if the toe is refined enough, it can also elegantly pair with a suit for a very British or throwback American look.

What Kind of Jeans to Wear with Loafers

• Pair more casual loafers (suede, rounded toe boxes, chunky soles) with more casual denim (lighter color, baggier, fades)
• Sleek and smooth loafers pair best with fitted, darker colored jeans

There are so many types of jeans, and the differences between them matter when paired with certain types of loafers. Generally speaking, the lighter the denim (in shades of blue), the more casual it is. The darker the jeans, the more elegant the loafers you can wear.

This, of course, always depends on the fit, though. A smart, sleek loafer will always need a fitted dark wash denim. A suede loafer looks good with lighter wash jeans, or even your white jeans.

Wide Leg Jeans and Loafers

More relaxed jeans are okay for a relaxed loafer, but never a sleek one. Baggy jeans are simply not appropriate for wearing with most loafers, especially almond-toe sleek loafers. Your spectrum of jeans should fall between slim, fitted, to relaxed. In my opinion, never wear baggy jeans. (Hey, this is an op-ed and style is subjective.)

But our Gen Z representative disagrees with this millennial’s aversion to baggy jeans.

“I think you need something a little bit wider or baggy,” says Alejandro, who likes a more cerebral approach to mixing styles. “Even with the dressiest kind of loafers, if you’re wearing jeans, you should go proper wide because I think if you’re wearing something this formal, you’re already kind of making a statement by making it like anti-formal. So make the clash deliberate.”

Look: Alejandro is a dyed-in-the-wool menswear enthusiast who knows how to bend and break traditional style “rules.” For the average guy, I advise against wearing smooth black loafers with jeans.

It’s almost like doing denim on denim — it’s not that it can’t be done, but it’s risky and it takes more effort to do well than most guys would want to put in. The proportions, fabrics, and fits must be perfect, or you’ll be silly.

Straight Leg & Tapered Jeans with Loafers

For guys who want to dress as uncontroversially as possible (isn’t that most of us?) your best bet is a straight leg jean.

“When in doubt, stick with a timeless straight-leg,” explains Alejandro. “Full Count’s 1101 (or a classic 501 repro) is ideal; if you prefer something slimmer, pair tapered jeans with a tapered loafer. Just avoid the super-skinny cuts.”

In this day and age, you also have your tailored jeans. Many custom suit makers offer the ability to order tailored jeans in a dress trouser style, with pleats and all. I have some lovely denim trousers by Yeossal that are Gurkha style (above on the left), and I wear them as if I would wear a dress trousers, with sleek loafers to match.

Can you wear skinny jeans with loafers?

Personally speaking, I wear skinny jeans with loafers. But I think that it really depends on your frame. If you are a heavy-set guy, then skinny jeans and loafers won’t look right. But a stick-thin guy can get away with skinny jeans and loafers.

There is also a fine line between skinny jeans, fitted jeans, tapered jeans, and jeggings. Jeans shouldn’t hug your calf like spandex, and those won’t look good with loafers. They can be slim but still have an allowance.

The younger generation agrees that too tight is not a good look, but they still lean baggier.

“Straight-leg jeans, think classic 501s, are your go-to with loafers,” says Alejandro. “Super skinny, ankle-hugging jeans never fly because they show too much sock relative to the cuff width — they just look off.”

What we do agree on is that the slimmer the jeans, the sharper the loafer must be. A skinny jean and a chunky, wide-toe loafer just don’t mix. It is apples and oranges and won’t look right. A sleek loafer requires a sleek jean. And this is where ‘skinny jeans’ (within reason) come into play.

What Socks to Wear with Loafers and Jeans

There are usually two rules of thumb with socks: match your jeans or match your shoes.

More often than not, I wear dark blue socks with my dark denim jeans and loafers. On occasion, if I am feeling bold, I might add a contrasting sock, though Alejandro and most of Gen Z seem to consider contrasting socks to be a dated style that screams ‘aging Millennial.’

Anyway: it’s best for your socks to match your jeans. If you are wearing black loafers, it is easy and safe to wear black socks. But the safest bet is always matching your trousers when your trousers are dark. If you have light jeans, I usually opt for a neutral shade of sock, on the lighter side. Maybe a light grey or a light brown if you are wearing a brown loafer.

Do not wear athletic socks, please. It doesn’t look good. I know that there is this new, revisited Trad trend of wearing long white socks with loafers. That’s really not my thing, although I am pretty sure that Alejandro partakes in this every now and then. If you do so, do it with purpose.

“I love pairing loafers with white socks and jeans,” nods Alejandro. “It’s a foolproof, combo that’s easy to grab and adds just the right touch of visual interest to simple outfits — even if the internet hates it.”

But don’t ever wear a low-cut sports sock with loafers. If you want one answer to the sock question, keep it simple: wear dark blue dress socks. It won’t glare like a lighter color sock can do. Darker is always safer when it comes to socks with loafers.

Wrapping Up

Loafers and jeans can absolutely work together, as long as you put a bit of thought into how you’re wearing them. From suede penny loafers to sleek black tassels, the key is matching the formality and shape of your loafers with the fit and wash of your jeans.

Casual loafers call for relaxed jeans, while refined leather like black calf pairs best with a more fitted, darker colored jeans. Ultimately, wear what feels like you, but know that getting the fit and balance right makes all the difference.