Shoe Etiquette : The Loafer General Style 54 Comments

JKISSI : If you have grown tired of the standard lace up, such as we do from time to time, the loafer is a great starting point to change paths from your usual choices. The loafer isn’t the primary item of choice when you’re thinking of purchasing a pair of shoes over other designs, such as the oxford. The casual slip-on shoe originally made it’s way from Norway in the 1930s and was dispersed all over Europe and took the interest of American visitors. When discussing loafers I can’t help but think about the high-fashion luxury house Gucci expanding on the classic design by placing a gold emblem on the loafer. The loafer is still known as an American classic in footwear whether you choose to fancy the shoe, or rather stay as far away as possible from what some people label as “grandpa” shoes.

Timeline – Originated in 1876, Bass shoes have become an American standard for comfort, durability and their own unique style. The company’s formal name is GH Bass + Co. and was named for its founder, George Henry Bass. Everyone knows the Bass Weejun penny loafer, a company staple.

SE, Street Etiquette, Joshua Kissi, Loafers men style, men style, loafers style, mens loafers, brixton hat, white jeans, penny loafers style

JKISSIBrixton hat – Uniqlo turtleneck – TM 3/4 jacket – Dexter hand-sewn loafers

Fit Description – I should have probably formed a post on head wear prior to this post as I have been on the search for great selections to throw on top of my cerebrum. I came across Brixton, a brand I have known since their humble beginnings back in 2006 when their head wear couldn’t really fit into my then-street-wear-oriented outfits. Yes , I’m in white jeans after Labor Day. For me, this so-called “fashion crime” has polluted some people’s minds regarding what they can and can not wear depending on the season. As you can see, I disregard this traditional notion as it’s outdated. When you think about the loafer who doesn’t think of the late legend Michael Jackson known for his black loafers and white socks accompanied with cropped trousers.
Travis Gumbs, Street Etiquette, Uniqlo Trench, Topman knit scarf, Sebago boat shoes

Trav pictured above with tassel loafers from Sebago


The penny loafer has been a American staple and classic go-to for decades now. There seemed to be a time when every boy and teenager would wear penny loafers comparable to the sneaker game of today’s generation. It was interesting to learn about what the extra leather slit provided on the penny loafer; from money for the payphone back when dimes were enough to make a call to a simply stylish approach. Even my Dad was pretty convinced to give the penny loafer a chance and change up from his usual selection of oxford shoes. The penny loafer is versatile being the perfect medium between casual and formal.

Street Etiquette, Travis Gumbs, Joshua Kissi, Tassel Loafers, Sebago Tassel loafers, Burgundy loafers tassel, SE, Bronx,


Have something to say?


  • damien

        posted on December 14 , 2009 :

    You guys are doing it for sure! I’m feeling the loafer as well and it is definitely classic American no matter how you rock it. Great post!

  • Chris M

        posted on December 14 , 2009 :

    I have a pair of Dexter longwings with an odd sole but I don’t know much about the brand. Do you have any background on them? Also I’m digging the loafers for sure.

  • Philipp

        posted on December 14 , 2009 :

    Love your outfit. As usual ;)

  • Jeff

        posted on December 14 , 2009 :

    Great post fellas. I’m liking the Brixton hat Josh. That’s funny how you got your dad switched his footwear to penny loafers. That’s all my dad wears are loafers haha.

  • Prêt-à-Porter P

        posted on December 14 , 2009 :

    i read somewhere (i think via wiki) that the penny loafer got his name because ivy league boys back in the day wanted to distinguish themselves so they started putting coins in the slots of their shoes, hence the name “penny loafers.” as always both you guys color coordination is on point. people that use the “no white after labor day” rule annoy me. especially when people say it living in FL, where white and flip flops are a year round thing. usu. the people that use that rule are a mess anyway.


        posted on December 14 , 2009 :

    Damien : Thanks Damien took a look around your blog and stumbled your post on loafers , I need to get my hand on a black pair like yourself. People usually go with either cordovan or black leather I have one down now it’s time to start on the other lol. Nice blog

    Chris M : You bring up a interesting point because I tried to get some information on them also, from what I gathered is that they now produce shoes for big retailers and bowling companies all around North America. I picked up my loafers from a thrift shop , it seems now they just focus on sourcing for bigger brands and not really their own

    Philipp: Thank You always

    Jeff : Thanks Jeff like I said in post was on that search for some great hats, came across this one and instantly fell in love with it. I know I know emotional stuff lol , but I would recommend going into the store to try on hats like anything else to see if it suits your face/look. I think I tried on about 10 different designs/colors of hats and settled on this one and it’s pretty good.

    Yeah my Dad NOW after me wants to purchase a pair I’m pretty sure he’ll love them I don’t know if it could top his love for oxford shoes with so many years, but definitely a great change up. Lol my dad needs to take some advice from yours it seems.

  • sk

        posted on December 14 , 2009 :

    I had absolutely NO idea that the slit was to insert a dime or a penny!! Thank you for teaching me something new today!

    While I should be learning allllll about what my final is on tonight, I am going to bed with a small anecdote of American shoe history. Thanks!!

  • components of enthusiasm

        posted on December 14 , 2009 :

    yooo, im mad you kids stole my kicks haha! nah i got those same pennys from sebago, brown and all, so smooth. im thinking about picking up those new modernized bass weejuns soon. saw them in gq, really dug their profile. great stuff again fellas!


  • Michael K

        posted on December 14 , 2009 :

    What a wonderful post and set of close-ups.
    You’re pieces on classic garments are a joy to read.

    I would recommend you take a look at Mr. Hare – a new label launched in London last year.
    He does a beautiful looking loafer with a slightly rakish off centre tassle called Mr. Genet ( I don’t think it got picked up in retail this season, but there is always hope for the future.

  • Tiffany

        posted on December 14 , 2009 :

    Very nice shoes.

  • Pascal

        posted on December 14 , 2009 :

    very nice outfits and love these loafers :-)


        posted on December 14 , 2009 :

    Pret-a-porter : Thanks for the additonal info there seemed to be many different reasons sos I rather let everyone hear them in full, ivy league situation sounds pretty accurate but its probably the combination of everything. Yes, the white jeans thing is funny especially among males because I see a few ladies still wear white denim/pants past labor day with some cognac leather boots or some sort.

  • Rhamier A

        posted on December 14 , 2009 :

    Mannnn lol im wearing my Weejuns right now as I type this. I was so close to doing a post like this last night but decided to postpone it. Looks like you beat me to it! I love the outfits, and this is no suprise that its a great entry. You guys are very consistant with what you do, and I appreciate it to say the least. Keep it up!

  • tommie_gunz

        posted on December 14 , 2009 :

    maaan i jus a wore turtleneck the otha day…mad heads was turned def. a good look. LUV THE BLOG keep up the good work


        posted on December 14 , 2009 :

    sk : Aha Great! , that’s what we’re all here to do is learn and expand our brains since your a female I wouldn’t expect you to know all of that off the back, lol studying we all know how tedious that is especially since its finals week for a lot people grr! lol you will be perfectly fine.

    components of enthusiasm : Lol thanks paul like they say great minds think a like , yup this is definitely the first step I’m definitely going for the black weejuns. Always been a fan of loafers though suede preferably because the cleanness it provides , like red suede would turn me out! lol keep up the good work on the blog Paul.

    Michael K : Thanks Michael I’m so happy to see you still read the blog you remember us from being primarily on Lookbook.NU , we have slowed down on posting over there but boy has it grown to another level happy for Yuri and the whole team over there.

    Thanks for the recommendation everyone should check it out , I think I have seen their name around on style salvage’s blog , looks great!

    Tiffany : Thanks!

    : Thanks my brother I’m definitely a fan of your work from photography and the blog you run. We need to somehow work together in the future let me know if you ever come stateside. Guys check out his blog interesting stuff to bookmark for daily reads. Another great male fashion blogger who will make his presence felt in the fashion/art world.

  • Mat

        posted on December 14 , 2009 :

    Great post as always

    On a side note: Seeing a tweet of a new post in the morning always makes my day a bit better….Street Etiquette goes so well with eggs and OJ


        posted on December 14 , 2009 :

    Rhaimer A : Lol we got it first! this post has been postponed for a very long time though so it’s great to finally see it finished. Thanks man we kind of took a bit on the post but we think the wait is well worth it we’re trying to get things to 2 post a week, thanks for the props man you already know what we’re building.

    Tommie : I love turtle necks one I have always looked forward to the colder weather just to simply put turtlenecks lol . On a more serious note they’re the perfect piece to layer with being jacket or blazer , sports coat it may not be for everybody because some people are not fond of highlighting their neck for various reasons.

  • Maura

        posted on December 14 , 2009 :

    Very nice shoes. Love the outfit.


        posted on December 14 , 2009 :

    Mat : Thanks , it makes my day much easier also just knowing that we have completed the hard part , now on to the easy part of communicating with our great readers such as yourself who fuels us to keep going with everything!

    Maura : Thanks a lot

  • amit

        posted on December 14 , 2009 :

    i like the coat a lot.

  • Kadeem J.

        posted on December 14 , 2009 :

    just gave me a good idea for a look to put together…

  • Roxanne

        posted on December 14 , 2009 :

    I just love you guys style. It’s so refreshing to see black men who are truly stylish!

  • Anonymous

        posted on December 14 , 2009 :

    i think i might have to invest into a pair of loafers, my grandfather has about 6 pairs, i wasn’t really a fan of then because my father always told me they weren’t very business like but, you guys make it look very fashionable, GREAT POST MAN!

  • Attila

        posted on December 14 , 2009 :

    My man legit got pennies in em! Great fits guys, I’m leaning towards travs just a tad. I think the white pants are a little too contrasting josh. Looking forward to the video. Keep it up guys

  • oldskooljunky

        posted on December 14 , 2009 :

    Awesome post! like that everythings going oldskool!

  • joseph a

        posted on December 14 , 2009 :

    im assuming the next post will probably have something to do with bow ties?

  • LOLA

        posted on December 14 , 2009 :

    You guys always amaze me!!
    It’s so funny because on my previous post I posted about my worn out loafers..
    but I always wondered about the name “penny loafers”
    AHA I just remembered that I met Travis at TopShop (well in TopMan) and he was really humble!
    lol he probably wont remember that anyways, BUT it’s great how humble and nice you guys are!

    Keep up the great work :)


        posted on December 15 , 2009 :

    Both outfits are dope! Info on the maroon colored gloves??

  • Luis Valdizon

        posted on December 15 , 2009 :

    Hey Joshua,

    It’s Luis from I recently started a new personal blog, to get down my thoughts etc and I posted about the penny loafers aswell.

    I must say although I don’t like the pennies in my loafers personally something about your pictures made me dislike them less.

    Anyways, I’m just checking in. I was wondering if you could add my new site to your blogroll it would be very much appreciated.

    All the best,

    Luis Valdizon

  • dayinthelyf

        posted on December 15 , 2009 :

    your whole outfit jumped off the page with those white pants. Trav got on assorted shades of brown too. do i forsee a post entitled ‘mocha obsession”?

  • Ragermac

        posted on December 15 , 2009 :

    Great look as always. I use to wear penny loafers back in the 80s and got away from them. I might consider them again. Keep the styles coming.

  • The Ca$h

        posted on December 15 , 2009 :

    You guys look great as usual.
    Keep up the Good Work & Fashion…lol

  • sssence

        posted on December 15 , 2009 :

    Dig both outfits. Great choices from each of you and each very distinct looks. I’m on the hunt for a pair of loafers now, hopefully in Oxblood. Joshua, the way you mix your color palette just continues to impress me. Trav, I love the warm feeling that your ensemble exudes and the balance of dark, rich colors with “winter white”. For me, white after Labor Day is a must and those that still stick with the old adage of “no white after labor day” are sorely behind on the times…
    Nice work once again fellas.

  • wale

        posted on December 15 , 2009 :

    whats up Josh. well written and informative as usual, never have been a loafers guy, kinda like you with sandals lol, but I really appreciate this post. the way the socks highlight both fits is my favorite part of the images, well done SE.

  • aidan

        posted on December 15 , 2009 :

    Very nice fits, both of em. Ive been wearing some cheap tassel loafers I got at goodwill, I really like the change from sneakers, which is what I wear most of the time. Ive been tryin to find some corduroys lately, Trav what kind are those in the pic? might have ta cop a pair

  • cam

        posted on December 16 , 2009 :

    ive always liked the loafers witha tassle


        posted on December 16 , 2009 :

    Amit : Thanks man it should suit you very well , thanks for the good words in our brief convo.

    Kadeem J : Glad the post could do that I know you will come up with something sick , just want to thank you for passing down to do the video my brother it’s much appreciated.

    Roxanne : Thank you so much for the good words we know what your talking about I guess it’s one step at a time in a long process.

    Anonymous : Wow 6 pairs of loafers I definitely agree with that I guess why people are quick to call them ‘Grandpa’ shoes lol, but I would def like to have more than that, yeah they could be worn as business for the office with some great trousers and a sharp shirt.

    Atilla : Thanks man! appreciate it , yeah I know people would like the contrasting , but I liked it burgundy/white is a perfect combo to me just like white with anything lol you know, that’s just how I feel though

    oldschooljunky : You’re right! History constantly repeats itself!

    Joseph A
    : No not at all , why did you guess that? lol its in the radar though somewhat

  • Nik T

        posted on December 16 , 2009 :

    I Have a pair of OxBlood Dexter Penny loafers much like the ones you are rocking in the picture. But the weird thing is that the Penny slot, the seams are closed (glued) so I can’t put the penny in? I have seen this before on other brands. Am I supposed to force the glued seam to get the penny in or are they a defect. It just seems strange, And I don’t want to wreck the shoes. Were yours like that too when you got them?


    P.S love the site and the Dopeness

    Nik T

  • David

        posted on December 16 , 2009 : Where do I start? I just just thought of your post as classic, seeing you in the fit caught me all off guard and Trav geez. You guys are definitely taking people to the stores with these fits here. Okay, enough of telling you guys what you already know, I see that you took some thought about posting this man it shows. I was thinking about how the trench coat could be in included in a similar post like this, seeing as it is the fall/winter season. Also, I like how you actually throw a pair of “pennies” in your “Penny Loafers”. It makes those and it also breaks those depending on who you talk to about that. Anyway, I think it is a good look because it keeps the authenticity pure in the pennies. As far as Trav’s pair the Sebago loafers are the tits especally with the tassles. Which as we both know, is a fairly new addition to the loafer’s original model. Overall, this is one of my favorite post of yours to date. It is dope once again keep it coming.

  • Jing

        posted on December 17 , 2009 :

    for me, wearing loafers is a way to “dress up” in summer

    inspired by the post, I just posted a ladies’ loafer update :


        posted on December 17 , 2009 :

    LOLA : Hey Lola thanks for dropping the comment yeah when ever I meet people on the street from the site or who know of us always try to treat them with the most respect just like anyone else. People are always surprised on how humble we are, but the reality is without readers you wouldn’t exist so to be grateful is another great thing to just do. : Thanks my friend the gloves are from Topman

    UPDATE – They’re on sale for $6.00 right now take advantage !
    Topman fingerless burgundy gloves

    Luis Valdizon
    : I definitely remember you from WDIR , that looks like a great blog man love the format of pictures and topics you cover. You are family from back in the day glad you found another venue to display your passion in , you have our support from Street Etiquette Luis, don’t be a stranger my brother.

    Actually I thought with the addition of the pennies in the slot gave them that “extra dash” to the footwear, not everyone looks for that so it could definitely varies,

    Reggie : Thanks man appreciate it , lol I thought people would’ve caught on by now we love earth tone colors or atleast I could speak for myself always a brown/tan/camel/dark chocolate brown thrown in my outfit somewhere , not unexpected at all.

    Ragermac : Thanks my friend you should definitely dig deep in that closet to resurrect those loafers. It’s not like they’re not “in style” classic shoe design you could bring out of the closet in 2030 that’s the great thing about staples.

    The Cash : Thanks , surely

    sssense : Hey Nicholas thanks for the great compliments oxblood would be super cool , you should scour ebay and see what they could help you with, possibly a great steal and deal in your size.
    Yes, people would apply that more to the “fashion” world which is different from personal style where you do what you want not thinking about ‘rules’ or ‘regulations’ that’s what we like to represent even though we are fans of the fashion realm.

    Thanks Nicholas for everything.

    Wale : Thanks lol sandals and me will never mix even if I was on a beach in the middle of the Caribbean

  • Poetri

        posted on December 18 , 2009 :

    It’s funny to watch your style evolve over time. You guys grew from kids to adults and the clothes say it best. Loafers are a classic staple for the working man and I’ve been looking for some ill loafers like those brown ones to wear to work. Nice post.

  • Anonymous

        posted on December 23 , 2009 :

    Why are you all so tragically obsessed with how you look? Sure, I like clothes and taking an interest in my appearance, but such obsession with detail and brands is unhealthy.

  • SwanDiamondRose

        posted on December 25 , 2009 :

    loafer love. absolutely. i have 60s, 70s and 80s versions. all of them varying ever so slightly from the classic. tasteful and even some tasteless versions. i love them. i love tiny tassles. why? don’t know. but i do know that loafers have just enough detail to freshen-up and make an outfit crispy. love them.

  • Rich

        posted on December 26 , 2009 :

    Hate to break it to you, but those Bass Weejuns aren’t Cordovan leather, they’re just regular leather.


        posted on December 26 , 2009 :

    Rich :Thanks for the insight.. I hate to break it to you but none of the loafers above are produced by Bass , we’re wearing Dexter and Sebago.

  • John

        posted on January 4 , 2010 :

    All shoe fashions change but its nice to see a fresh look for the loafer – 60′s inspired fashion seems to be back in a few weeks ago I saw a girl looking great in chunky tasseled loafers looking so different from what most girls wear.
    I like late 60 fashion.
    White socks no problem its all about getting the detail right

  • mars_concepts

        posted on February 26 , 2010 :

    I love good music and I love sharing it as well, checkout this new mix to wrap up the month of February, titled Penny Loafer League Session 1.

    Penny Loafer League Session 1:

  • hughthomas (Hugh Thomas)

        posted on March 8 , 2010 :

  • Gary

        posted on March 11 , 2010 :


    I stumbled upon your site while searching for penny loafers. Would you mind telling me what color the Dexter hand-sewn loafers are and where you found them? I’m looking for a classic pair of penny loafers to wear with some dressy chinos and the ones in your photos look great.

    Thanks. Love your site.



  • PatPoon (Pat Poon)

        posted on March 29 , 2010 :

    Saw these Tassled Sebagos today in black – may go back and cop them…

  • DinTX

        posted on April 25 , 2010 :

    hey – just snagged a pair of Dexters from EBAY- i’d been wanting Weejuns for a while and had just about given up. thanks to you i came across the Dexters – hand made, leather sole and i dig the pinking shear’d tounge… cant wait put get em and slip em on… i’ll be rocking them with my white painter pants come May… bring on the summer in TX… Keep up the good work, DinTX

  • mens loafers

        posted on August 10 , 2010 :

    Out of all the styles out today these are on the top 5 of my list lol. great site btw

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