How to Wear and Style Loafers (2023)

You don’t need to spend hundreds of dollars to get a reliable pair of loafers. The go-to for many people is the G.H. Bass and Co. Weejun. A pair will run you right around $170, or even less if you don’t mind wearing them secondhand. Dr. Martens loafers have become a popular option with a more casual spin that’s available in a ton of colorways for $150 (a bit more if you want to snag the Supreme collab off the secondary market). There’s also plenty of affordable brands that will charge even less than $150 for a pair if you need something in a pinch. Just don’t expect them to last as long or be as comfortable. If you want to invest a bit more into a pair to up the quality, Blackstock & Weber sits in the middle of the pack, with most pairs retailing for $375, and offers up colorways to match any style. Danish brand Vinny’s sells its loafers for around $300 (but look, an amazing sale!). While we want to make sure you know that you definitely don’t need to spend around $900 for Gucci loafers or over $1,000 to get a pair from Prada, we all love splurging on some luxury goods every now and then. If you can afford it, go for it. We don’t blame you.

Chris says: “I think that if you can't get a pair of mine, then you should save your money. When you spend almost $400 with me, you get a lifetime shoe. I can't say that for everybody else. There's a lot of great loafers out there. But I stand by the fact that ours are the best in the world.

There's all these different factors that I think are good reasons to purchase something. A bad reason is, ‘I wanna stunt on somebody because I have the Guccis.’ Then, you're just doing it wrong. If you think the Gucci is the best-made shoe out there, then you're completely wrong. But if you want the name, if you like that silhouette, go get it. But there's plenty of other stuff out there you can get that look off with."

With loafers, you may have steered clear of them because you think they aren’t versatile like a pair of sneakers. And while we aren’t here to tell you they are as versatile as sneakers, you can definitely toss them on with a pair of shorts or some sweats. You can look presentable. And no, you won't look you're in a frat. A pair of solid-colored nylon shorts or chinos that sit above the knee is a great look in the summertime. Next time you need to run to the grocery store, toss on a white T-shirt, your favorite hat, and some sweats with your loafers. Wearing them casually like this is also a great way to break them in (more on that later).That doesn’t mean you should try to pull off your new loafers with that jersey for your favorite sports team on Sunday this NFL season or your favorite pair of Mitchell & Ness shorts. Don’t try to wear them with some cargos either. But have some fun with it. You may stumble into your new go-to outfit in the process.

Chris says: “You have to make sure that something works proportionally for you. There are people that are too tall to wear shorts with loafers and it doesn't look right. There's guys that are too short to wear sweatpants with loafers. But one of my favorite outfits is just a T-shirt, pair of sweatpants, and loafers. You can go on a drive, to the corner store, to walk the dog, and it doesn't look crazy.

[Wear] your regular Champion sweats that your dad had, with the old-school cuff. I’m a big fan of cutoff denim shorts. You can do a mesh short, not an NBA basketball short, always above the knee.

If you’re a first-time buyer of some loafers, you may assume you should buy the same size you wear in sneakers. Don’t do that.

Like most hard bottoms, loafers typically run big. Personally, I wear a size 11 in most sneakers and wear a 10.5 in loafers (my foot is a bit wide). If you don’t have a wide foot, it’s recommended to size down one full size from your regular sneaker size. They’ll feel very snug at first and honestly may not be the most comfortable right out of the box, especially if you spend most of your days in some New Balance 990s or Nike Air Maxes. Expect a blister or two, and some sore toes. Just be patient. They’ll break in gradually the more you wear them. Before you know it, you’ll be able to spend hours in them with no issues.

Chris says: “Get 'em as tight as you can take 'em. It's leather. It's gonna expand as you wear it. That's just the way that it works. Think about the future. People think about right now and they're like, ‘Oh, I should get a half size up because it's a little bit more comfortable right now.’ But later on they're gonna have a shoe that's slipping off of them because it grew an additional half size. It might hurt a little bit, but you're building a shoe that's going to be molded to your foot.

It depends on how often you wear your shoes. I think by the third or fourth all-day wear you should be good.”

If loafers always seemed like a boring shoe that only your grandparents wear, that’s far from the case anymore. Yes, classics like some brown tassel loafers are still easily accessible (and should be considered), but they make loafers in plenty of materials and colors these days that allow you to really add a statement piece to your outfit. Blackstock & Weber certainly leads the charge in this category with creative executions that have included canary yellow pebbled leather, a mix of animal prints that remind us of Atmos’ classic Air Max 1s, and opal blue hairy suede. Echevarria doesn’t put many limitations on his material choices. Just don’t expect some loafers made out of nylon or suiting fabric any time soon. Some things are still off limits.

Other brands like Duke + Dexter are also making some interesting loafers that you may have seen across your social media timeline. Certain pairs feature a rattan vamp inspired by the brand’s knit shirts, while other pairs feature colorful paintings of lemons or tranquil landscapes. And these are just a few examples. Do some exploring. You’ll be surprised at how many eye-catching options you come across.

Chris says: “One of the reasons why I started the brand was just to show people that this can be as versatile as a sneaker, as far as color is concerned. I think getting outside of the box is super important because now you can take that same thing that people traditionally said was boring and move it into a more interesting territory. A loafer was just seen as a business casual shoe; now it's something that can be a conversation piece.”

We don’t mean to make this seem like the most outlandish thing to do. People have been wearing loafers with some jeans for years. But some people, especially if they don’t wear them often, may not think to pair the classic slip-on footwear with some Levi’s 501s. In my opinion, lighter washes look best, but it really all comes down to personal preference. Try different fits too. A straight leg pair falling over the front of your loafers may look best with one outfit, while cuffing your jeans to show off some sock may be what you prefer with something else. Just don’t go too baggy or it will start to look a bit messy. When it comes to what tops to pair with your loafers and jeans, pretty much anything is on the table. We’d probably just stay away from T-shirts with wild graphics. Solid colors or minimal logos look best. But again, everyone’s style is different.

Chris says: “A lot of ‘80s and ‘90s style was jeans and loafers. It’s sharp but dressed down at the same time.

I'm doing it all. Big cuffs, little cuffs, slim jeans, big jeans, letting them drape over with a little frayed hem on them, cropping them up. It all depends. You gotta figure out what's right for you.”

Yes, loafers are being worn more casually these days, but don’t forget that they’re still a perfect option when you need to dress up. Don’t feel like wearing some lace-ups to the next wedding you have to attend? Try a pair of black or brown loafers. Have a big dinner date with that special someone? Maybe it’s best to leave the Nike Dunks in the closet for a night in favor of some horsebit loafers to add that extra bit of class to your ensemble. Toss them on with an Oxford shirt and some perfectly pressed chinos for that next job interview. We personally would recommend keeping things classic and going with black leather, brown leather, or black with a white vamp. But if your style is more eccentric than that, just ask Chris. There’s no reason to limit yourself.

Chris says: “Wedding. Bar mitzvah. Prom. I just sent my cousin a pair of shoes for prom. You could do 'em with a tux. And you don't have to [keep it classic], man. I went to a wedding recently. I wore a midnight navy tuxedo and some black pony hair loafers. You can go crazy.”

We get it. There are certain shoes that we only save for certain seasons or a weather forecast that’s juuuust right. While there are still reasons to abide by those types of rules, like if you just bought a pair of peach suede loafers and the weather report says it’s raining all day, more often than not you can slip on a pair and hit the streets without stressing. There are also tons of brands making lug-soled loafers now that are more geared to dealing with the various terrains of the outdoors. The lug sole also provides a much more casual look if you feel that the usual loafer sole is still too dressy for your taste.

Chris says: “Loafers are an all-year-round shoe to me, especially when you start to add Vibram on it. You can wear loafers in the rain if they are leather. If they're suede, don't wear 'em in the rain. But just wear 'em, bro. Wear 'em. That's how you break 'em in.”

It’s easy to obsess over keeping your footwear as clean as possible. And we don’t blame you. We aren’t saying to walk out of the house with your loafers caked with dirt looking like a sorority girl’s Air Force 1s. But don't stress about having some creases in the leather or a small scuff. It adds some character. Shoes are meant to be worn.

There are still some worthwhile upkeep practices to abide by. Keep a rag on deck to wipe down your pair if for some reason they get super dirty or dusty. Also, please don’t try to just step into your loafers like they’re some shoes you slip on to take out the trash. Invest in a shoehorn. Ruining the structural integrity of the heel is silly, and you’ll regret it later. Plus, there are mules if you want something to slip on with ease.

Chris says: “Beat 'em up. You shouldn't really need anything more than a wet rag. If you get a scuff or something like that, take it to the cobbler because they know how to take care of that shit. Other than that, drive ‘em like you stole ‘em.

You got to have a cobbler on deck. There's usually one in every town. Ask your mom and your pops, and they know where they are. You need to go to a cobbler to get your shoes resoled.”