How Men Should Style Loafers, from Casual to Formal | Expert Advice from a Tailor

Here’s the deal: loafers aren’t just for summer. These versatile shoes can take you from casual outings to weddings, formal events, and work settings — really any situation where you want to wear comfortable slip-ons that look relaxed yet sharp and polished. But such versatility begs the question, how do you style loafers?

To find out, we hit the streets seeking out the foremost menswear experts in New York City — hounding them until we narrowed down these do’s and don’ts.

Our Experts

Nick — Stridewise Editor-in-Chief — met up with his good friend Alejandro Jomar, who is a tailor, menswear expert, and style vlogger (check out his YouTube channel here), to talk about loafers and how to wear them. We also recruited our pal, shoemaker and brand foudner Justin FitzPatrick, who contributed to our more specific guide on how to wear loafers with a suit.

Our Style Categories

When it comes to categorizing looks and outfits, we’ll break it down into four categories of dressiness:

• Casual
• Smart casual
• Business casual
• Business professional/formal

Let’s get started with casual and work our way into more formal settings from there.

How to Wear Loafers with Casual Outfits

• Penny loafers, beefroll loafers, and chunky loafers are the most casual loafer styles.
• Remember the sleeker a loafer, the harder it is to wear casually (and the better fitting your clothes should be)
• Brown leather is more casual than black.
• Suede is more casual than smooth leather.
• Prints and colors are more casual than solid colors.

Loafers can absolutely anchor a casual outfit. Consider wide jeans with a t-shirt, loose chinos and a button-up, or chino shorts and a polo. Look for flatter, wider loafers like Oak Street and Grant Stone‘s, our personal favorites.

If you got a beefroll style loafer, you could take it in an extra casual direction, though it’s a bit harder to integrate into a more formal outfit. The beef roll has puckering around the stitches, which isn’t as sleek or elegant as you want for a dressier outfit.

“I usually like to start with a nice brown loafer for summer,” Alejandro says. “And then wear it with a light blue Western shirt and a nice straight-leg or wide-leg pair of raw denim jeans. You could wear this in the summertime if you want to, but loafers, again, are not exclusive to summertime.”

What About Loafers With Shorts?

With even casual loafers still being dressier than beat up sneakers, it’s smart to wear a collared shirt when pairing loafers with shorts. A polo or Hawaiian shirt as pictured above is still plenty dressed down, but easier to wear with loafers.

“I wouldn’t wear black loafers with shorts,” Alejandro says. “But anything that’s light colored, cream, brown, or tan. Maybe even blue loafers with shorts and a t-shirt. And I would probably wear a hat with the outfit.”

(Nick’s in a summer straw from Two Roads Hat Co above.)

If you’re going really casual, wearing shorts and a t-shirt, try to stick with suede loafers in a tan or brown color. If you prefer smooth leather over suede, that’s fine, too — just go with a casual penny loafer or beefroll in a brown leather and make sure the t-shirt fits well and doesn’t have a band logo or something on it.

“When I wear loafers with shorts, I wear Venetian loafers,” Alejandro explains. “They don’t have the top strap [as seen on a penny loafer] or moc toe stitching. A good example of a popular Venetian loafer is Astorflex’s Patnoflex that I found on Huckberry.”

Loafers are an easy way to dress up just about any look, including shorts. Just make sure your clothes aren’t too baggy!

Our Favorite Casual Loafers

With shorts or with chinos, we always find ourselves coming back to these two standouts: Oak Street’s Beefroll for its classic Americana good looks and rare, genuine handsewn construction; and Astorflex’s Patnoflex for an ultra lightweight Venetian-style loafer that’s also more affordable.

Smart Casual Outfits with Loafers

• Smart casual means no shorts or t-shirts.
• Collared shirts, like a polo or button down are best.
• Short sleeves are fine, but it’s best to tuck the shirt once you’re smart casual.
• While un-faded denim is accepted in smart casual environs, chinos are a safer bet.

“Smart casual is a step above casual wear, but not quite business casual. It’s about creating a polished look with intention.” explains Alejandro. “To nail the smart casual loafer look, consider pairing them with well-fitted, dark wash jeans and a collared shirt. “

Another smart casual outfit tip for the warmer months are white jeans.

“One of my favorite outfits in summer is white jeans with a blue polo shirt and loafers. To me, that’s a really nice smart casual outfit,” explains Nick. He also loves the look of white jeans with loafers and a pink linen button-up shirt for a splash of preppy color.

The key to mastering smart casual with loafers is maintaining clean lines and a cohesive look while avoiding overly formal elements. Remember, “Smart casual is about looking good, put together, and comfortable all at once.” Nick emphasizes. “It’s the perfect middle ground for those occasions when you want to impress without overdressing.”

Long story short: wear a collared shirt and relatively fitted garments.

The Most Versatile Loafer

If you’re after one loafer to take you to as many places as possible, consider these two: the just-almond-shaped-enough Meermin tassel loafer or Grant Stone’s Traveler: it’s just roomy enough at the toe to fit in anywhere, plus they have tons of sizes and widths.

Business Casual Outfits with Loafers

• Play it safe with an Oxford cloth button down, well-fitting trousers, a sports coat, and loafers.
• Wear socks with your loafers: the safest option is to have them match the pants.
• Even with a tie, such an outfit would be considered business casual because the jacket and trousers aren’t part of a set.
• Wool trousers work, but chinos and corduroy can be worn here.
• You can wear jeans in some office settings with an Oxford shirt and loafers, but it’s best to ask ahead if jeans are acceptable.

Men tend to like firm rules to dress by (hey, we’re the sex that’s less creative with their fashion), so here’s a simple formula for the business casual outfit: an Oxford cloth button-down shirt, chinos or wool trousers that fit you perfectly, and a sports coat, combined with loafers. You basically can’t go wrong.

As we’ve gotten older, we’ve started enjoying a tie with such a fit. You’ll still look business casual simply because the jacket doesn’t match the pants, which is the crucial differentiator between a suit (business professional) and an outfit that’s “casual” (at least in an old fashioned sense).

As for trousers, wool trousers are classy way to add texture to your outfit that works with either smart casual or business casual looks.

“You’ll often see wool trousers, also used for business casual, in a smart casual look with loafers,” Nick says. “It’s doable, but you don’t want to have a silk shirt or something particularly dressy on top that’ll push the look into more formal territory. I just always stick to Oxford cloth shirts and tweed jackets so that I don’t have to think about it.”

Oxford shirts and loafers are a match made in New England/preppy style history that will always have timeless appeal and always work well together.

“I actually love wearing Oxford cloth shirts with brown loafers and jeans,” Alejandro says. “A lot of people have started wearing jeans to the office. There are some business casual atmospheres where that is acceptable, but you’d want to confirm before turning up to the event that jeans fit their definition of business casual, because it’s not always the case.”

The Best Business Casual Loafers

Once you’re getting to tie levels of dressy, you should look for a more almond shaped toe and less pronounce moc stitching.

Business Professional: How to Wear Loafers with a Suit

• For a business professional look, choose sleek, polished leather loafers in dark colors with understated stitching.
• Black calfskin is the default for dressier footwear.
• Consider black tassel loafers with a grey double-breasted suit, white shirt, and blue or black tie, as you see above.
• Penny, tassel, and horsebit loafers are acceptable here, provided the leather and last are dressy.

Loafers can look great with a suit as long as they’re the right kind. Your Cliff notes: a smooth leather in a dark color (ideally black), subtle stitching on the moc toe, no beef rolls, and look for a sleeker, almond shaped toe.

For a business professional look: try black calfskin tassel loafers with a black double-breasted suit, a pleat on the pants, a white shirt, and black tie.

If it’s a scenario or setting where you’re wearing a tie, go with a simple, non-chunky, sleek, and shiny loafer. Carmina Shoemaker is a really storied, great European dress shoe company — their most minimalist loafer styles pair as well with a suit as any oxford shoe

“The tassel loafer offers a bit of ornamentation here, so these often show up at formal events and are a menswear staple in some circles,” Nick adds. “The tassel helps you add a bit of oomph to your outfit — and if the loafer is in a smooth, black leather, you can see them looking amazing with a suit.”

While opinions on loafers with suits differ by country, you should be in good shape if you adhere to the rules of black calfskin and a slim toe.

“If we’re giving advice to guys new to this world, go with a classic model, penny loafer, calfskin leather,” says Justin FitzPatrick. “Black is always going to be more conservative, more classic. It goes with navy, it goes with gray. Brown’s a bit more modern and takes a little more work to match.”

The Best Professional Loafers

If you’ve fantasized about wearing horsebit (or “Gucci”) loafers with a suit, you can do so with the right leather. Or you can go with a penny loafer from the king of European dress shoes, Carmina Shoemaker.

Other Considerations for Wearing Loafers

• What’s considered “dressy” varies by country.
• Brown suede is usually considered the most casual leather, but Italians often wear it with suits.
• A penny or tassel loafer in smooth brown leather will get you the most bang for your buck.

Some countries have different “rules” about how formal certain loafers are. For example, in England, wearing loafers with a suit was, for a long time, considered something that you shouldn’t do — especially not a brown loafer.

“In America, you’ll find guys on Fifth Avenue wearing horsebit loafers with suits, in England, you’ll find guys wearing sharp penny loafers with a chiseled last with their suits, and lots of guys in Paris are wearing Andy Berluti style loafers with ties and everything,” says FitzPatrick. “And then you go to Italy, and that’s the king of brown suede loafers with navy suits and ties. So it depends, and it depends on the formality of the occasion as well.”

Another major factor as to whether you wear loafers is the weather. If you’re traversing the streets in major rain or snow, you will probably want to go with a shoe or boot with better traction (unless you’re wearing one of those chunky, lug sole loafers). You don’t want to get a sleek, calfskin loafer covered in mud or salt.

How to Wear Black Loafers

• Black loafers can be worn casually, despite being generally more formal than brown loafers.
• For a smart casual look, pair black tassel loafers with slightly faded, wider-leg black jeans and a looser top to dress down the leather loafers.

Black loafers may be more formal, generally speaking, than brown (especially brown suede) loafers, but that doesn’t mean that they can’t be worn casually as well — they are slip-on shoes, after all.

“One of my favorite smart casual looks includes a black tassel loafer,” says Alejandro. “I’ll wear with these with a pair of black jeans that are on the wider leg side, in a little bit of a washed down, muted shade. The black leather dresses the outfit up a little bit, which balances the looseness of the pants.”

That said, black loafers are pretty hard to to dress all the way down to shorts. Cover your legs with these harder edged shoes!

How to Wear a Chunky Loafer

• Chunky loafers, characterized by thick soles, are more casual
• Pair chunky loafers with a button down shirt tucked in and baggy or wide-leg jeans for an easy, stylish look

A chunky loafer is just what it sounds like: any pair of loafers with thicker, more prominent soles. These are casual loafers, but the chunky loafer is in its own category and experiencing a resurgence in popularity.

Dressing them down is also easy — and frankly, fun.

“I love [a good pair of] chunky loafers with baggy jeans, wide leg jeans,” Alejandro says. “With chunky loafers, I feel like it kind of removes the cerebralness of dressing and it’s just so easy to wear them with a simple outfit.”

Chunky loafers look great poking out from under a wide leg pant, but with straight leg jeans, you have to be more conscious of how the pant falls over the shoe. In particular, be sure to avoid slim fit or skinny jeans.

How to Wear Loafers with Shorts

• No visible socks
• Brown suede is the best leather
• Go with a rounder toe

Shorts with loafers is a classic summer look that can also show up well in the spring or fall when weather permits. While it’s much more comfortable to wear socks, we don’t recommend wearing visible socks with loafers and shorts.

With shorts, a suede loafer works well since it’s the least formal and most breathable leather. If you’re specifically looking for a summer loafer, we strongly recommend unlined suede and leather soles, like these Meermins, for the extra breathability.

Wrapping up

We hope these tips on how to style loafers prove helpful, from knowing the types of loafers to exploring the different categories of formality. Whether you’re sporting classic loafers or your favorite loafers are platform cow-print, we hope these tricks and guidelines help you pull together the perfect look and make the fashion statement of your dreams.

Best of luck with all of your loafers, present and future!

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