How to Wear Loafers - Fall/Winter - Justin Jeffers/J Butler

Loafers Explained: How To Wear & Style Loafer Outfits in Fall & Winter with Jay Butler

If you recall, a few months ago we had a conversation about how to style loafers during Spring/Summer season, and today, we’re going to let you in on how to combine loafers for fall/winter outfits that rock!

Outfit 1: Corduroy

Outfit 1: Corduroy

Sven Raphael Schneider: Alright, next up we have green corduroys.
Justin Jeffers: Yeah, so it’s kind of like a Christmas look here.

SRS: For holiday parties.

JJ: Yeah, you could wear it for a holiday party, or if you’re going to a Christmas party, maybe that’ll be a sweater party, and me personally, I’m not a fan of ugly sweaters. I don’t know if I see you wearing ugly sweaters.

SRS: Maybe, if it’s a themed party, why not? Probably not as a joke or something.

JJ: Yeah. So, the idea here is to create a great holiday look, but it’s truly a great fall and winter look. We picked the green and red because of Christmas, and we kind of brought down that theme or toned down the theme a little bit, with a navy cashmere sports jacket and a navy tie loafers. It creates a really conservative, really classic look, and you can easily swap out the green pants for brown pants, or you can even maybe do a white corduroy or a cream colored corduroy, it’ll still be a really nice looking look.

SRS: We’re a little more colorful again, you like bolder colors which is nice.

JJ: Yes.

SRS: We’ll show the full spectrum here.

Outfit 2: Resort Look

Outfit 2: Resort Look

JJ: This is a very playful winter look. This look is not for a lot of guys; it’s very colorful, very neon, very adventurous. Kind of a throwback to the 80s with the neon colors and the fleece.

SRS: Resort look kind of.

JJ: Yeah, so this is like your apres ski look. Maybe you’re on the mountain, and you’re sitting by the fire, you want to kind of just relax, or maybe you’re at home and you want to take it easy, you’re having a night in with your girlfriend.

SRS: And you want to stand out from the crowd in a bold way.

JJ: Yes or maybe you’re going out to the bar or the corner store, you want to show a little bit of leg or you want to have fun with your look. We chose a caramel, lighter brown colored shoe to go with this look because it kind of plays off the beige and the yellow of the lining of the pullover, and also of the pants. Again, it’s not a look for everybody but I love this look, I wear it out, it catches a lot of looks and ladies always ask about it, which is an added bonus.

SRS: Yeah, next look, I mean fair isle sweaters, I really like them. Very classic, Prince of Wales’ well known for his picture.

JJ: Yeah, he kind of made that famous when he was golfing. It’s a great classic look and what’s awesome about a fair isle sweater is you can pull on a lot of different colors from the sweater.

SRS: Yeah and the sweaters only work because they have this nice mottled yarns and they are actually many different yarns so it’s very easy to combine because it picks up on all kinds of colors.

Outfit 3: Fair Isle

Outfit 3: Fair Isle

JJ: Exactly! So what we did here was we took the fair isle sweater and we took the suede shoes and we have two different options for the pants to show that you know you have the shoes and you have the sweater but what are you going to do in between? Well, you could easily do a navy blue pair of pants, corduroys, chinos or a brown pair. I think it’s important for guys to realize that the looks we’re showing here are not regimented. You can swap out any given item for anything else.

SRS: It’s inspiration. It’s food for thought.

JJ: Yeah!

SRS: Like showing you something that you might not think about.

JJ: Yes.

SRS: So it’s all about food for thought. It’s like show you something that you might not have thought about otherwise.

JJ: Yes and the other thing going back to our early points is the setting. Maybe during the day, you want to wear the brown corduroys but maybe at night you want something a little more formal, a little darker, so you go with the navy blue corduroy.

SRS: Right the next look is a little bolder, a leather jacket in here.

Outfit 4: Leather Jacket

Outfit 4: Leather Jacket

JJ: Yeah so again we have a little more fashion-forward look. It’s not something that I would wear and or something you would wear but for a lot of guys, this is a great look. You know we’re here in Los Angeles at the Art of Charm headquarters this would be a great look for Los Angeles or maybe New York or perhaps Miami. We took a leather jacket, a beautiful black leather jacket with a Henley shirt. You know sometimes I wear a Henley without any other shirts, I think it’s a great look. It’s a more rugged look. For the pants, we have kind of a black – it’s kind of a cross between a jogger and a chino. And then, of course, we put black shoes with that. We went with the Shipley Tie loafer in this case because I think it paired best with the rest of the look. But you could easily swap out those the tie loafers for a penny loafer.

SRS: Alright.

JJ: Keeping with the black theme, we stuck with a black sunglasses and black wallet.

SRS: All black.

JJ: All black everything.

SRS: You know sometimes guys want a slightly more modern look.

JJ: Yes.

SRS: Right now, camos are fashionable especially for younger people.

JJ: So this look there’s kind of two focal points. It’s the camouflage as Raphael alluded to and there are the white jeans. In the old school, you don’t wear white between Memorial Day and Labor Day. There’s no such thing as winter whites. In the new school thought the more modern look as you spoke of, you can wear white in the winter. So we took a white denim jean here and we paired it with a…

SRS: A thicker fabric probably.

JJ: It’s nice thick fabric with a great quilted Navy top and the camouflage jacket which is kind of combination of a couple of different trends. But it ends up being a very classic kind of preppy look but with a different twist on it. More kind of a new school prep look.

SRS: Definitely.

JJ: In the wintertime it’s great, you can throw on a hat and you know we have the navy suede penny loafers that really bring in the color of the camouflage jacket down to the shoes to really again frame the pants that you’re wearing.

Outfit 5: Camou

Outfit 5: Camou

SRS: It’s that common concept – framing the pants.

JJ: Yes.

SRS: Using the loafers and the jacket.

JJ: Yes.

SRS: It’s a theme that we’ve seen across many different outfits.

JJ: Yes.

SRS: Whether it’s Spring/Summer or Fall/Winter.

JJ: And what you’re doing a great with your outfit right now you have kind of the orange in your pocket square and the orange in your shoes which the watchers can’t see, but it’s a great orange boat shoe that Raphael is wearing.

SRS: Next we have a good flannel outfit. It’s not your Grandpa’s flannel outfit.

JJ: No, we changed up your typical gray or navy flannel and did a lighter blue flannel. I think it’s a beautiful fabric. To me, tweed and flannel are the two fabrics of the winter and fall season. Flannel is the more formal of the two. So we started with the flannel suit, and we wanted to do a monochromatic look, so we took a light blue shirt, navy blue suede bit loafer, and then the Navy knit tie which I think may actually be a Fort Belvedere tie. You guys have some great knit ties.

Outfit 6: Flannel

Outfit 6: Flannel

SRS: Thanks! We usually say monochromatic. To me, monochromatic invokes this like you know all gray, gray, gray with very light variations. Now technically navy is a shade of blue and so is a blue suit. But to me, they are so contrasting that to me it won’t be quite monochromatic. You know what I mean?

JJ: Yeah. The same you know the color family but yeah it’s different enough but the same. I think it gives off a very sophisticated, very elegant air and also shows that you’re very much in control of your own personal style.

SRS: Absolutely.

JJ: Which I think is very important especially when you’re wearing a suit.

SRS: Yeah. I mean with this suit, it’s definitely a little lighter in color which makes it bolder, so you toned the rest down. You took the tie then it kind of match the shoes so you can frame everything which is that recurring theme we’ve been talking about with the outfits.

JJ: Yes and blue is also great because it works well with a lot of guys, you know with complexions and hair colors. So I think this is a very flexible look it’d be great if you’re maybe having a dinner party or a night out, a nice date, maybe an anniversary or something like that.

SRS: Next up we have like a sweater. A lot of guys like to wear sweaters. So thick ones, 6-ply, ply yarns. What did you do here?

JJ: So we actually found the sweater and fell in love with the sweater. It, as you’ll see in the photo, has a lot of different shades of brown that are in the sweater that is woven through. It has a nice chunky knit, and the Raglan sleeve is also kind of unique. We ground that with a brown khaki and then the brown penny loafers. It’s a very simple kind of very minimal look. It’s different enough that it’s not plain, it’s not boring. We have the texture of the sweater which is really really nice.

SRS: And it’s just like a more muted outfit. You have the mottled winter white yarn and going with the green-grey pants and then just go a shade darker for every item towards the bottom basically.

Outfit 7: Sweater

Outfit 7: Sweater

JJ: Yeah and if you know if you wanted to change this outfit up, you could easily throw on a navy blue cable knit sweater or a burgundy v-neck sweater under maybe a white oxford cloth button down. It’s a really flexible outfit with the brown shoes and the brown pants you can almost do whatever you want on the top color-wise which is really nice.

SRS: Personally, I’m a big fan of dinner jackets and while I would not necessarily wear a pair of loafers with them, maybe a pair of slippers or velvet slippers. What’s your take on it?

JJ: Obviously, I’m biased on this one because I design loafers and I love loafers. I wear them eight days a week and any chance I have to wear loafers; I’ll wear them. A lot of guys may not be for them. They want to wear you know when you said a Prince Albert slipper or lace up, or an Oxford. I think this look; the idea was to create a look that is very nonchalant, very elegant, very masculine. So we took the velvet jacket, it’s that nice deep burgundy color which looks great on a lot of guys. It’s unique. The women love that feel of the velvet and the look of the velvet.

SRS: Because of the light – the artificial light, it sparkles. It’s just a unique look, and you will get lots of compliments wearing that.

JJ: Yes, a lot of compliments and of course it’s one button on the front, and it’s peak lapel which is very important. We did everything else there is quite simple. I mean the black…

Outfit 8: Dinner Jacket

Outfit 8: Dinner Jacket

SRS: Shell color would work too.

JJ: Shell color also will be great.

SRS: And no notch.

JJ: No notch. Never notched. You also see some sort of jackets that have the shawl lapels which is great or the frog closure on the front which is also a great look. The idea with pairing the tie loafer with this look was something that’s playful- adventurous but still masculine but kind of played off of the unconventional nature or the less common nature of the velvet jacket on top. So I think the penny loafer will work with this look. The bit loafer would work with this, but the tie loafer is really great because it is to me the most kind of playful of our shoes and really of any loafer type. You can even see an Italian gentleman wearing a black driving shoe with velvet jacket if you really wanted. I think the look like this is great if you’re at awithss formal black tie event, maybe a black tie optional event or if you’re hosting a black tie event at your house or an art opening or something like that. I wouldn’t wear it to a wedding or more formal black tie event but those that are less formal I think this is a great outfit.

SRS: I mean for most people black tie is very formal, but there are some, where you can have these more casual black ones. I mean I wear dinner jackets at home or for parties sometimes in winter. I like them, they’re fun, but I’m also like a dressier guy so having these dress codes make it fun for people to experiment.

JJ: And some guys get bored just wearing a tuxedo at the same time, every time over and over again. It’s nice to change it up little bit.

SRS: Last but not the least, we have a nice a sports coat outfit here.

Outfit 9: Tweed

Outfit 9: Tweed

JJ: This is a great look. I think it’s a great Fall/Winter look. This look I think is a great fall and winter look. It’s a nice heavy tweed jacket. We started with a jacket and said okay what can we pair with a jacket, it’s very bold strong statement. This jacket you have there, the kind of the rusty brown color with the light blue check. It’s not a common color combination, and you really have to pair it down and pair it with other neutral and earthy tones. So we took the cream-colored cashmere turtleneck which when you don’t want to wear maybe a tie or an open-necked shirt like I’m doing right now I think a turtleneck is a great alternative especially in the fall and the winter. It looks very sophisticated, very composed.

SRS: It’s really popular now. You’d see a lot with people having the turtleneck. I personally am not super fond of it. It can look good, it’s a personal thing, right? It’s more casual than having the tie. I like wearing neckwear. If you get a cold easily, I think turtlenecks can look good.

JJ: Yes, I agree on that and great point. At the bottom look, we took an olive green flannel pants. It’s a really heavy flannel. It really pairs well with that thick heavy texture and kind of muted look of the tweed.

SRS: It’s beautiful.

JJ: Thank you, and at the base of that, we took the caramel penny loafer. The caramel obviously ties in really well with the color of the jacket and the penny loafer. I think, given the strength of the jacket and also the turtleneck something very simple at the feet is really what you wanted to look like this. I think this is a very sophisticated, elegant look and one that you can easily change out the colors but keep the principles the same. You have a great tweed jacket maybe have a brown or navy or red tweed jacket, maybe switch out the green pants for a gray, or navy pants. I think you have a really great look it’s a more of a higher level look. It’s a little more adventurous, a little more out there. I think it’s a great look.

SRS: Awesome, I agree. Previously we already discussed how we can combine loafers in Spring/Summer as well as in Fall/Winter and if you haven’t already done so please check out our loafer guide and if you want to go to Justin’s website where should they go?

JJ: You can find out more about Jay Butler at, and you can email us at, and if you have any questions we’d be happy to answer.

SRS: Absolutely. Awesome. Thank you!

JJ: Thanks, Raphael.

Loafers Explained: How To Wear & Style Loafer Outfits in Fall & Winter with Jay Butler
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Loafers Explained: How To Wear & Style Loafer Outfits in Fall & Winter with Jay Butler
Get inspiration from these dapper fall/winter loafer outfits with none other than Justin Jeffers.
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4 replies
  1. Kenneth Geathers says:

    I would like to know since the loafers can be worn in the fall/winter season wouldn’t a man’s feet freeze? Especially in the 20’s and single digits? I always learn and thought that boots plays the role in the fall/winter season. Thanks!

    • Alexander_F says:

      I can only agree this question is justified. I may be a wuss, but personally, I can’t possibly imagine wearing loafers in winter.
      Otherwise, the outfits are really well selected, by the way.

      • Kenneth says:

        Cool! I agree with the outfit organizing;however,here in NY it’s impossible to wear loafers in the fall/winter season since the weather temperature can become extremely cold! I personally would wear boots to protect me feet and ankles!

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