Loafers Explained How To Wear & Style Loafer Outfits in Spring & Summer with Jay Butler

I’m here with Justin Jeffers, the man behind thefineyounggentleman.com and the shoe brand, Jay Butler.

Today we will discuss how you can wear and combine loafers with items in your wardrobe and also talk about what events they are appropriate for and when you should not wear them. If you want to learn more about the history and everything that goes into loafers. Please check out our in-depth loafer guide here.

Sven Raphael Schneider: Justin! Thanks for being here.

Justin Jeffers: Raphael, Thank you very much for having me. It’s a pleasure.

SRS: Great time here in LA at the Art of Charm headquarters?

JJ: Yes, it is.

SRS: And, I wanna mention loafers with you. I mean we had a good conversation with them and you taught me more about the details of them and you also have some good ideas of how to wear them.

JJ: Yes.

SRS: So, I think most people associate a spring/summer style with a loafer. What do you think are good outfits to combine it to?

JJ: Okay, well first thing, thank you, Raphael for having me it’s a pleasure. Been a big fan of the blog for a long time. So I think, loafers to me are perhaps the most flexible type of shoe you can wear. More than a sneaker, more than a boot, more than a lace-up. You can even easily dress them down or you can easily dress them up. I mean, you can really wear a loafer with a tuxedo if that’s your style, a bit loafer for instance. You can wear it with a suit, a double-breasted suit, a single breasted suit, you can wear it with a bathing suit. They really can cover the full garment of style. So, I got a bunch of looks here today, and a couple pair of shoes we can talk about. And like you said, we can go over what situations you can wear them in and also different combinations. How you’re going to dress a loafer down and how you’re going to dress it up.

SRS: Absolutely.

JJ: So I think for the first look, let’s start with a more casual look. I’m a big fan of wearing blue, my hair and eyes are dark brown so blue works really well for me. So, this look here, you’ll see.

SRS: I mean that being said, blue works for many men and women, it’s a wardrobe staple because of that. So it’s something most men can wear.

JJ: A hundred percent. So, in this look here, we have a pair of an air force blue seersucker pant which you can easily swap out for a pair of navy chinos or maybe cobalt blue chinos, a light blue button-down shirt, and a pair of brown penny loafers. The brown penny loafer is the most practical, the most wearable penny loafer of all loafers, really. Any guy, every guy should have one of this in their wardrobe.

SRS: I agree with you on that one. We talked on a loafer guide and I think one thing that you do that’s great is that you offer the matching belt. So people can kind of come by that, pull off that look very easily.

JJ: Both at Jay Butler and thefineyounggentleman, I get a lot of questions on (a.) “What color of pants should I wear with what color shoe?” and (b.) “What color belt should I wear with what color shoe?”. I’m of the school of thought, you may agree or disagree, but I think you should match the color of your belt with the color of your shoes.

SRS: Unless you have the casual option, I think you sometimes can have a madras belt or a fabric belt.

JJ: Or like a needlepoint belt, something like that.

SRS: Exactly, or like a silk tie like Fred Astaire would wear it

JJ: And as a back-up, you can match your belt to the upper of the shoe, you can match it to the sole color. So, for instance, we have a navy blue suede shoe and I think if you can’t wear a navy suede belt or you don’t want to, a brown suede or a dark brown belt that matches the dark brown of the sole works very well.

SRS: Alright, excellent.

JJ: So Raphael, this next look here, we base the look around a pair of brown suede bit loafers, for us it’s the Millbank Bit Loafer. We did a really simple, really casual outfit. You may wear it to brunch on the weekend or maybe out on a date on Wednesday night. We took a pair of tan chinos with a green polo shirt.

SRS: Dark green, raisin green.

JJ: Yeah, very simple outfit, very casual. If you really want, you can throw a jacket over it, a vest, if it’s cold out and then we pair a suede belt to go with it and you’ll see a watch and sunglasses to go with it.

SRS: Yeah, personally, I also think it would look great with an olive green one, maybe don’t wear red polo otherwise you’d look like a—

JJ: Christmas tree? You don’t want that.

SRS: Exactly.

JJ: The next one we have here is probably the most casual look we’ll discuss today and that’s a bathing suit. You know, some guys don’t want to wear flip flops.

SRS: It’s a bold bathing suit too.

JJ: It is a bold bathing suit. It’s a great bathing suit though, it’s Orlebar Brown. Some guys don’t want to wear flip flops to the beach, and I get that. They don’t want to have their toes showing, and I think a loafer or even an espadrille is a great option for that.

SRS: It could be a resort town, or where it’s warm, tropical, you know when they’re always on the sand.

JJ: Exactly.

SRS: Sometimes I find it that when you’re on sand and you get the sand in the shoe, it’s not the most comfortable thing.

JJ: No, it’s not. So we paired the caramel penny loafer with this bathing suit. For me, the reason I chose the caramel is because I though the caramel paired well with the yellow of the surfboards in the bathing suit. So, if you’re not wearing a shirt, you know, basically you’re wearing a bathing suit, I think it’s wise to look for colors in that bathing suit that you could either match or that you can complement.

SRS: I mean caramel or tan are just great colors for in the summer it’ll look whiter and less formal, but you can still wear them with a dark pair of chinos or something in Nantucket red for example, or regular seersuckers, no problem.

JJ: Yes, and then tequilas for obvious reasons. Another really casual summer look are shorts. You can wear them with a longer short, in this case we have a shorter short, they’re actually chubbies

SRS: What do you mean by shorter?

JJ: So these shorts, I believe are 5″ in seam. Most shorts are 7″-9″ in seam. For most guys, I think anything more than 9″ is too long. You don’t really want to cover your knees.

SRS: No, it has a 90s look.

JJ: It cuts off your legs.

SRS: And it’s not very advantageous.

JJ: Yeah, it does not flatter many guys.

SRS: So, what you got here.

JJ: So it’s very casual. Again, we have here the brown penny loafer with a brown belt to match it. The dark brown, I think, really grounds down the red of the shorts and the blue of the gingham in the shirt.

SRS: Exactly, it was already a bold choice, so you tone it down on the shoes.

JJ: Yeah, you tone it down a little bit. You can easily swap out the bit loafer here or even the tie loafer. We want the penny loafer again to kind of subdue the outfit a little bit.

SRS: So, about the shirt, short sleeve shirt, long sleeve shirt?

JJ: In this case, it’s a long sleeve shirt. Personally, my style is I don’t wear short sleeve shirt button-up shirts, so my shirts are long sleeve.

SRS: I’m with you, like if I want that look I just go with a polo shirt or I have a regular shirt and you can always kind of roll up the shirt sleeves.

JJ: Yeah, which is a great look. Very casual, kind of I’m off duty, I’m relaxing type of look. So, let’s talk about a couple more dressy looks.

SRS: Alright.

JJ: The first one we have here is just your classic navy suit, every guy probably has one in their closet. So a lot of questions that are directed towards me, both again in the blog and also at Jay Butler, are, “Can I wear these loafers with a suit?”

SRS: Yeah.

JJ: Generally speaking, I’d tell guys the tie loafer and the penny loafer are not quite formal enough to go with a formal suit such as this navy blue one here. More casual suit, let’s say a seersucker suit or a linen suit or even a blazer or a sports jacket, any of the shoes would go well with it. That goes just not with our loafers we have here today but with a more formal penny loafer, even with a driving shoe, and even with an espadrille.

SRS: Okay.

JJ: Especially in the warmer months. But what we have here is what I deem to be the most formal of our loafers is the Bit loafer. The dark brown goes really well with the navy blue. Dark brown, being a little bit more formal than the caramel but you can easily wear a caramel bit loafer with a navy blue suit or even a black bit loafer.

SRS: Yeah, totally. And also it always depends on how you do it right? If it’s like your most formal interview. Let’s say if you’re in Italy and if you’re in a lighter shade of navy, maybe if you skip the socks altogether or you have no-show socks or some like inserts, it’s a different look but it depends on what the purpose is.

JJ: What the setting is.

SRS: exactly.

JJ: And who is your audience, you want to think about who you’re speaking to, who you’re communicating to with your clothes, you can change up the accessories and the small details of your outfit.

SRS: So, with the suit, would you wear socks with your loafers or would you skip it?

JJ: Typically, yes. Especially if you’re going into more formal office environment, if you’re going into a bank or an accounting firm or a law office, yes.

SRS: More over the calf socks, anyways.

JJ: Yes, especially from Fort Belvedere. Many times with loafers, you want to wear a thinner sock, the fit of loafers is different than lace ups because you don’t have the laces to tighten or loosen the shoe. So if you’re used to wearing loafer without a sock, if you all of a sudden wear a thick sock, it’s going to significantly throw off the feel of that loafer.

SRS: Oh, totally. So, would you say like silk or cotton?

JJ: The thin silk or cotton even wool works, there’s a lot of really thin wool socks that can work really well.

SRS: Alright.

JJ: Especially in the summer time you want a really thin sock. Another formal look we have here and this may be my favorite look we’re gong to go through today, is what I’d like to call, “The Summer Soiree look”. You’re going to a cocktail party, a garden party, maybe even a rehearsal dinner at a destination wedding. We have a great pair of linen and silk brown pants, which is a very classic pant, most guys will have some version of this.

SRS: I mean it’s soft, like the silk gives the linen some softness but you have this texture, it keeps you looking summery. Maybe if a guy doesn’t have it, you can still wear a pair of chinos, but it’s something to aspire to, it’s something to work for.

JJ: Yes, and so my thinking behind this outfit was, keep the pants and the shirt very simple because we have a very, very strong jacket.

SRS: Absolutely.

JJ: The navy with the dragon print is not admittedly for a lot of guys but for some guys it is right up their alley. You can easily swap this out for a navy blazer, a green jacket like you’re wearing, or even a herringbone or a summer herringbone jacket.

SRS: I mean, you’re a bolder guy yourself, you don’t shy away from strong patterns, you have these lilly pulitzer fabric in green, suspenders. It’s a bit of the personality, if you like it more subdued you can get a small checked summer blazer, and swap it out for this one.

JJ: Again, going back to our earlier point of the setting, if it is a more formal summer event, maybe you can swap out a pair of jacket for a simple blazer. In this look, what we did is we pair a navy blue suede tie loafer with this look. One thing I like to do for my style is to frame the pants, so we frame the pants on the bottom, thing for the frame, we have the navy blue shoes, and on top of the frame, we have the navy blue jacket.

SRS: Very good, I mean it’s a general concept you can apply to many outfits, not just this particular one.

JJ: Yeah, and for a gentleman, it helps draw the eyes kind of up. Here we have a casual look ideally for the summer, you have the shorts there, a long sleeve polo shirt which is great. At night maybe it’s a little chilly, you can throw over a vest on top of this, a fleece vest would look great.

SRS: I like the color combination, it’s not so bold, it’s like an olive green with a tan and a white, off-white.

JJ: Like an earth tone, almost.

SRS: Exactly, and I think green in general is one of the most underrated colors in men’s wear, so I’m glad to see that here.

JJ: Yeah, and olive green, I think, in particular is great because whether you’re wearing this on the early fall or in the summer, it will reflect the colors in nature. You also get that kind of classic, military olive green, which again is you said underused which I 100% agree with and it will flatter most guys’ complexion as well, which I think is very useful.

SRS: Yeah, how about a more formal look?

JJ: Okay, so this, again is another one of my favorites. You don’t see guys pairing loafers with tuxedos a lot but in certain circles, you will see it a lot. I think of loafers, you have your penny loafer, your driving shoe, your bit loafer, some guys would even wear Belgian shoes with a tuxedo, I think the bit loafer is maybe the most fitting of all those. Again, it’s the most formal, and I think the flash metal on the bit can complement whether it’s your cufflinks or your studs very well.

SRS: That’s true, it’s a great one. At the same time, historically, people would really like patent leather, or oxfords, or court shoes, unlike a loafer which comes up a little higher, has a little like a higher vamp, then you see a much deeper cut. Now I think, your loafers have the lower vamp, tell us more about that.

JJ: That’s a very good point, Raphael. At Jay Butler, we have two signatures to our style. The first one is, as Raphael pointed out, is a little shorter vamp. Vamp is the piece of leather that covers the top part of the foot. On many shoes, you may see a vamp that covers two-thirds of the foot. For me personally, I think that covers too much of the foot, it throws off the balance of the foot and the balance of the shoe. So I shortened our vamp, as you see in the ratio, to maybe cover about 40%-45% of the foot which I think, frames the foot much better.

SRS: Alright.

JJ: The other thing that is unique about our shoes is a very thin sole, and what comes with that is a slightly lower heel. Some loafers you see now have a very bulky sole, and a very tall heel. Which I think, again going back to framing the foot and framing the pant, it throws off the ratio of the pants and the ankle and the foot.

SRS: With a thinner sole, I mean, you get less cushion in. There’s no space for cork, at the same time it’s super flexible.

JJ: It’s super flexible, you don’t need to break them in. Out of the box, they’re comfortable.

SRS: Awesome.

JJ: To combat, that’s a very good point of not having a cork sole. To combat not having a lot of support, we added a little arch support here. Unlike many shoes, we have a full-length insole, so over time, your foot will kind of break in your shoe and the shoe itself will conform to your foot, so it’s very comfortable. It’s like your favorite pair of blue jeans, or you know your dress shoes, that you can tell your foot is the foot that’s supposed to go in that shoe.

SRS: Alright.

JJ: So let’s go back to this look. We pair the black bit loafer with the tuxedo. I think it’s a great look, it’s not for everybody, it’s a more casual look, but it’s kind of a subtle way to differentiate yourself from the rest of the guys in the crowd. The tuxedo is a tuxedo, you can change a couple of details on it but there’s only so far you should go, so the shoe is a great way to change it up.

SRS: So, one thing that you have which is quite unusual I think, is this perforated leather.

JJ: Yes.

SRS: You now, sometimes what happens is that they perforate on the outside but the lining is solid, so the purpose is not really given. With yours, you can actually see the lining as well as the top perforate, they’re both perforated and their lined up perfectly.

JJ: Yeah, so this is, in the summertime, my favorite shoe to wear. We make this shoe in the penny loafer and also the bit loafer. As you pointed out, a lot of brands will add a liner which aesthetically, you maintain the purpose of the perforations but from a functional perspective, you lose them. So, I like to tell my friends and customers that this perforated leather is almost like a leather mesh. On a day with a stiff breeze, you can actually feel the breeze come through the shoe and if it’s a very humid day, like we get in Philadelphia, where I’m at, or even if you’re in Arizona, and it’s super dry, it can just rip off the moisture right off the foot, which is really nice.

SRS: It’s the equivalent of a fresco fabric.

JJ: Yes, perfect. Fresco or linen fabric, and it really cannot be beat on the hottest of summer days.

SRS: In our style, it’s a little bit more casual, a little more unusual, it’s not quite like a classic penny loafer, it’s not quite a bit loafer.

JJ: It’s a little bit more adventurous, I like to say.

SRS: Exactly, it looks almost like a boat shoe.

JJ: Yeah, this shoe is actually what started Jay Butler.

SRS: Oh seriously? I didn’t know that.

JJ: Yeah, so this is the first shoe that I designed and the whole kind of impetus behind Jay Butler was to make shoes for gentlemen, for under $200, our shoes are priced at $195 but for under $200, where it was well made, it was well styled, and it was well priced. A lot of brands will maybe hit one or two of those criteria but not all three. The idea of this shoe was to have your driving loafer, I love driving loafers, but I have often found out that the nubs wear out too quickly, whether it’s a $100 pair of driving shoe or $500 pair of driving shoes.

SRS: Very true.

JJ: So, I took the sole, the leather sole, the leather heel of a penny loafer and put in on the upper of the driving shoe. So, you get the casual, adventurous, playful look of the driving shoe but the more substantial, more durable, more formal feel of a penny loafer or a bit loafer.

SRS: And it’s a little more structured still, you have that general construction but overall, that’s the thought behind it.

JJ: Yeah, and so it’s very unique, especially on the American market. It’s a little more Italian, little more kind of European in its look. So let’s start, here we have a tweed jacket, I know you did a great article.

SRS: Oh yeah, we wrote a tweed guide.

JJ: Yeah, it’s phenomenal. You covered the history of tweed, how to wear tweed, and so here, we took those principles in that guide and we were able to pair a tweed jacket with burgundy chinos and a bit loafer. You can wear socks with this, you can wear it without socks.

SRS: Looks nice.

JJ: Yeah, but the point is that you can easily wear the loafers and then loafers will stand out to the heavier fabrics of the fall and winter. They’re not going to be overshadowed by the heavier fabrics. This look here is maybe our most fashionable look. It’s not a look that I would necessarily wear but I think it’s important to show guys that you can wear loafers with not just the suit, not just the tuxedo, not just shorts. You can break from that kind of preppy mode, the loafers are kind of steep in preppy and ivy style but the way they’re worn these days, they’re worn with everything. Women would wear them with leggings, they’d wear them with a skirt, they’d wear them with jeans. Guys can wear them with pretty much anything and everything. So, what we have here is a pair of joggers, and I know you don’t like to wear sweatpants, I don’t wear a lot of them either. It’s a little too casual for me.

SRS: It’s just a possibility.

JJ: Yeah, it’s a possibility and it can actually be a really nice look. So we took a gray jogger with a white v-neck, and a brown motorcycle jacket and paired that with an olive green suede penny loafer. What we did here is we wanted to pair a bunch of unconventional items or maybe more adventurous items into one look, but still a look that is somehow conservative and not too adventurous. So I think the olive green suede, really pairs well with the brown suede of a jacket. We have those earth tones, and you have the neutral tones of the gray pants in between.