Tassel Loafer Style Guide: How to Get Down with the Dangle

Since its start as a custom shoe for a Hungarian Hollywood star, the tassel loafer has made its way to every kind of foot: from 1980s Wall Street snakes to student leftists to, well, me: a guy looking for a shoe that’s as easy to dress up as it is to dress down.

By gum, I think I’ve found it.

The tassel loafer is the most versatile loafer and maybe the most versatile footwear overall. But I don’t blame you if you’re puzzled by how to wear it or which kind of tassel loafer is best for you.

For this guide, I’m joined by two good friends: YouTuber-slash-professional tailor Alejandro Jomar and blogger-slash-shoemaker Justin FitzPatrick. Together, we’ll explain the ins and outs of wearing tassel loafers from casual to formal.

What are Tassel Loafers?

Tassel loafers (sometimes called tasseled loafers) are traditional moccasin-style slip-on shoes with decorative leather tassels where laces normally go.

Those are the constants, but individual models can differ by their shape, leathers, and soles. Some are dressier, some are more casual — we’ll get to that later.

“When I’m working with clients who don’t have any footwear that feels up to par with the clothing that they’re getting from me, I always recommend tassel loafers,” says Alejandro, a professional tailor by trade. “They can serve the best of your casual and business casual wardrobe. To me, they’re the perfect all-around shoe.”

Similar to wingtips, which originated as British country shoes, tassel loafers were originally worn quite casually — best known as footwear for college students — and then slowly became associated with business professional wear. Today, they’ve settled in the middle: tassel loafers can be appropriate for both casual or formal settings.

History of Tassel Loafers

The tassel loafer’s enduring popularity may be due to its hybrid origins: it’s an American invention inspired by a European.

According to Robert Clark, vice president and spokesman for Alden Shoe Co., Hungarian-born actor Paul Lukas asked New York shoemakers Farkas and Kovacs to combine European-style fringed tassels (which often decorated the tips of shoelaces) with a moccasin loafer in the 1940s.

Unsatisfied with the fit and hoping an expert could refine the prototype, Lukas sent one loafer to Manhattan retailer Lefcourt and the other to Los Angeles’ Morris Bootmaker — and they both independently asked Alden in Massachusetts to perfect the design.

Other important stops in this loafer’s history is Brooks Brothers’ 1957 introduction of an Alden version in burgundy shell cordovan, and George Bush using the tassel loafer as shorthand for sleazy Wall Street types: in 1992 he accused his opponent Bill Clinton of being supported by “every lawyer that ever wore a tasseled loafer.”

“Tassel loafers, now, I feel like they’re making a big comeback,” says FitzPatrick. “Whether they fit in with a suit or not is kind of subjective. It’s really just about how confident you are in pulling it off. I love loafers, so I wear them with everything — suits included.”

The Different Kinds of Tassel Loafers

• Light leathers and suedes are casual, black calfskin is the most formal
• Round and roomy toes are casual, almond-shaped toes are more formal
• The more pronounced the moc stitch, the more casual the loafer appears
• A tassel loafer in a smooth brown leather is the most versatile

Now to say all that in a more lengthy way!

The enigma of the tassel is that it adds just the right kind of ornamentation: it can make something dressy come off as more playful or it can make something casual come off as more ornate. Perhaps the uniting theme is that the tassel makes it seem more thoughtfully made, suggesting that it just belongs where it’s worn.

Like I said in my big guide to casual summer loafers, the rounder and roomier a shoe is, the more casual it is. Ostensibly, this is because you’d need roomy footwear to do work or engage in dynamic movement, so chunky footwear became associated with manual labor or physicality — things that are not formal. Conversely, an almond shaped toe makes a shoe more dressy.

On a similar note, a tall or luggy sole is much more casual than one that appears flat when viewed from the side, like a leather sole (which is especially common on loafers). Again, it’s because a durable and grippy sole connotes functionality, outdoorsiness, and (therefore) physicality — not the office or fine dining.

One more element to pay attention to is the leather: suedes and light colored leathers are more casual than smooth, dark leathers. If you want an unambiguously formal loafer, choose black calfskin.

So what do you get if you value versatility? Get something right in the middle: if the leather is smooth and brown and the sole is flat, you’ll be able to wear your loafer with almost any outfit. Mine are from J. FitzPatrick, but Grant Stone’s is another fantastically versatile option that’s got just the right silhouette to go anywhere.

How to Wear Tassel Loafers

The most versatile tassel loafers would be in a brown leather that’s relatively smooth and uniform. It would also have a flat sole that’s either made of rubber like Dainite or leather, which breathes very well for summer shoes.

If you prefer brown suede, that can be styled all the way to business casual with a tie, but it’s a bit iffy with a formal or professional suit.

Wearing Tassel Loafers Smart Casual

Loafers are the ideal smart casual shoe. I don’t recommend wearing tassel loafers with shorts, but if you’re following the rest of the rules in our smart casual guide above — which includes “wear leather footwear that isn’t black” — then you’ll find that the loafers will helpfully elevate your outfit to smart.

For example, many guys default to a polo shirt and chinos when the dress code says smart casual. You can get away with wearing minimalist sneakers here, but in cases like this I strongly urge you to opt for the loafers: they’ll bring your look one level dressier and make everything else you wear appear smarter and more thoughtfully chosen than sneakers will. (Yes, even if they’re nice sneakers.)

Wait, No Tassel Loafers with Shorts?

• I don’t love this look for most guys; it’s too far in the “preppy” direction
• If wearing shorts, stick to a penny loafer

Believe it or not, this loafer guy doesn’t love wearing tassel loafers with shorts. If you’re making the particularly casual (or particularly preppy) move of loafers with shorts, I think you want to keep the loafer as simple as possible: that means a plain old penny loafer, like my well worn Grant Stones or Oak Streets.

I think tassel loafers with shorts is aggressively preppy. Do it if you don’t mind that look, I’m just saying it draws more attention to your footwear than you’d probably want. It’s a look.

An exception is if your style is more modern or street and you’re wearing a chunky loafer from a brand like Blackstock and Weber, above. If it’s a luggy sole and a roomy build with a super casual leather like the options above, then they’re easier to wear with shorts because you’re just in a different realm to the classic Americana kind of loafers I’ve been emphasizing in this article.

In other words, chunky modern loafers make it clear that you aren’t trying to fit into traditional or vintage footwear and menswear. So if you’ve bought some of those, just make sure you’re wearing them with a contemporary outfit: if you pair something like that white soled bad boy on the left with an outfit that’s otherwise classic and preppy, like chino shorts and an oxford cloth button down, it’ll look all wrong.

Wearing Tassel Loafers with Jeans

• Relaxed, tapered, and straight fits work best, but avoid skinny jeans
• Brown and black leather both work

Alejandro and I also filmed this video above that’s all about loafers and jeans, and we emphasize a lot of the same points in this article you’re reading now: roomier and lighter colored loafers are easier to wear casually.

But Alejandro does like to break these rules.

“One of my favorite casual looks includes black tassel loafers.” he says. “I know traditionalists consider them dressy, but if you wear them with white socks and wide, casual jeans, then they can work great because there’s no ambiguity in how you’re dressing.”

He concedes that since it’s against “the rules” to dress down such smart loafers, you should try to keep the rest of the outfit simple — casual, but simple.

“Don’t introduce too many pop colors, if any at all,” he says. “You want people to look at the composition of the entire outfit instead of picking apart all the different details. If you’re including something incongruous like a black tassel loafer, you shouldn’t wear anything else, especially eye-catching. That’s the secret to making things work when you’re ‘breaking the rules.'”

But there’s one thing I always say when really stylish guys like this come on the channel: most guys don’t want to think so hard about what they’re wearing. So for most guys, it’s easier to just stick to that rule about keeping the loafers light colored.

Are Tassel Loafers Business Casual?

• Tassel loafers are excellent shoes for business casual
• Practically any tassel loafer with a flat sole, suede or box calf, works here

Tassel loafers are widely regarded as appropriate for business casual. Since you’re not wearing a suit and tie (more on that in the next section), pretty much any tassel loafer will do, so long as it doesn’t have a chunky sole.

Business casual usually means you’re wearing a sports jacket, and if you’re sporting tassel loafers that are more on the casual end, I’d urge you to wear a tie. Ties tend to be optional (though encouraged) when you’re business casual, but when you do wear a tie, it’ll lift the rest of the outfit and keep anyone from raising an eyebrow at a more casual tassel loafer.

“If I’m business casual in the office, I always go with the smooth leather just to be safe,” says Alejandro. “If I’m out of the office, I’m comfortable with suede.”

Business casual lets you dress less somberly than you would with a strictly corporate dress code, and Alejandro likes to bring in what he considers more “fun” and comfortable items like corduroy trousers or a seersucker sports coat.

“Here I added a blue tie to complement my blue and brown plaid sports coat,” he says of the outfit above. “I chose corduroy pants, but with this kind of dress code you could wear wool trousers or even chinos.”

Not sure if you’re quite dressy enough for business casual? That’s a topic for another article, but so long as you wear that “optional” tie and sport coat, you’ll be fine with any flat soled tassel loafer.

Can You Wear Tassel Loafers with a Suit?

• If the leather is dark and smooth and the toe is refined, yes
• Black calfskin is the best option for a suit and tie; but brown is sufficiently dressy
• But don’t wear suede with a suit

The short answer is yes, you can wear tassel loafers with a suit. It’s debatable, but if you make absolutely certain that you’re wearing the dressiest kind of tassel loafer — with a refined toe, leather sole, and dark (ideally black) calfskin — then it will fit in fine.

“Brown suede would work with, say, a summer linen suit,” Alejandro concedes. “But you really need to make sure you’re nailing the balance, and most guys aren’t interested in putting that much thought into constructing an outfit. So I’ll just say most guys should stick to black calfskin. Smooth brown can be okay, but not with a grey or black suit.”

Another tip for wearing tassel loafers with a suit: make sure the moc stitch is nice and subtle. A lot of casual loafers are made with genuine handsewn moccasin construction, which tends to produce a very conspicuous, very casual looking moc stitch.

When you’re dressing up, make sure your moc stitching is low and subtle like the Meermin and J FitzPatrick ones in the picture above.

Wrapping Up

That’s our expert-approved guide to tassel loafers. If you’ve read this far, you know the good news: tassel loafers are very versatile and pretty hard to mess up. That little tassel somehow manages to dress up a more casual outfit but also work great with a deliberately dressy one.

There are a few rules to follow if you’re wearing a suit and tie, but if the dress code is any less formal than that, it’s hard to go wrong. Just get one in smooth brown leather and call it a day.