Hilary Pollack

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. Key Takeaways: Loafers are versatile shoes suitable for casual to formal occasions. For casual looks, pair brown or suede loafers with jeans or shorts, avoiding logos on your shirts. In smart casual settings, combine loafers with chinos or nice denim and a collared shirt. For business or formal wear, opt for sleek, dark-colored loafers with suits or dress pants. A tassel loafer in smooth brown leather is probably the most versatile option. https://www.youtube.com/watch?vc1CDxvYdY68 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 founder Justin FitzPatrick, who contributed to our more specific guide on how to wear loafers with a suit. Further Reading 10 Best Loafers For Men Expert Tested | Horsebit, Penny Loafers & More We tested dozens of loafers before landing on our top 10 picks. Learn more → 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. Mean mugging in loafers. Left to right: Grant Stone, Meermin, and J FitzPatrick. 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. Those chunky rolls on either side of the penny strap are called "beef rolls" and they make a loafer more casual. (As do the playful socks.) 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. Two more casual outfits with Meermin loafers: Alejandro going urban, Nick going summer linen. "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." Get more casual, durable menswear tips from our YouTube channel! Subscribe Loafers with shorts: Grant Stone left and Oak Street right. In retrospect, these fits would have worked much better with chino shorts, like Flint and Tinder's. 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. Grant Stone's Traveler in their undyed "Dune" leather might be the world's most versatile loafer. "When I wear loafers with shorts, I wear Venetian loafers," Alejandro explains. "They don't have the top strap 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! Further Reading 7 Types of Loafers for Men We take a look at the most common styles of loafers for men. Learn more → 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. " Further Reading How Should Loafers Fit? The Ultimate Guide to Sizing Men’s Loafers We met up with a shoe fitting expert to get the best tips on loafer sizing. Learn more → Nick pairing Chromexcel loafers with tapered jeans from Oni Denim Co and a pink linen shirt from Todd Snyder. 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. Brown tassel loafers are probably the best bang for your buck if you also want to dress them up. 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). These outfits would be considered business casual in large part because the (wool) jackets aren't the same material or color as the (cotton) trousers. Nick's in cotton chinos and Alejandro in brown corduroy. 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. Alejandro's in business professional while Nick's still in business casual — both sporting tassel loafers. 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. https://www.youtube.com/watch?vtPMi4_pn1-0 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 Further Reading How to Wear Loafers With a Suit: 10 Tips for Looking Your Best We met up with Justin FitzPatrick, a shoemaker and menswear expert, to learn how to wear loafers with a suit. Learn more → Our pair of dress loafers from Carmina. "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. *Wes Anderson music intensifies* 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. Embracing the chonk of Koio's chunky loafers (which they discontinued) "I love 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. Loafers worn casually in Tuscany. 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! FAQs Can you wear loafers with jeans? Yes, you can wear loafers with jeans for a smart casual look. Pair them with well-fitted jeans and a collared shirt for a polished appearance. For summer, try white jeans with loafers and a polo or linen shirt. While chunky loafers work well with wide-leg jeans, be mindful of how straight-leg. Can you wear socks when styling loafers? Yes, you can wear socks with loafers, depending on the style you're aiming for. For dressier outfits, choose socks that match the shoe color or opt for subtle patterns to add character. With formal loafers, black socks are appropriate for business settings. For casual looks, white socks can be a bold statement, especially when paired with subtle, simple outfits. This trend works best with straight-leg or wide-leg pants, but avoid it with suits. What are Penny Loafers? Penny loafers are a classic style of slip-on shoe characterized by a distinctive leather strap across the top of the shoe, often with a diamond-shaped cutout. The name "penny loafer" comes from the practice of inserting a penny into the cutout for luck or fashion. Penny loafers are versatile, and can be dressed up or down, making them suitable for both casual as well as more formal occasions.