All Season Etiquette: Saddle Shoe Etiquette Read  -  General Style 71 Comments

JKISSI : As I perused through the LIFE archives I couldn’t help but notice the reoccurring appearance of saddle shoes during the previous mid-century.  Known as one of the few All-American classic shoes, the saddle shoes popularity began primarily around the 1940′s and 50′s. Identified by different names, such as saddle shoes or saddle oxfords, the shoe was intended for functional use for sports such as tennis and squash, but as you know, sneakers came into the picture and became the go-to “sport shoe”. The two-tone shoe was known simultaneously as classy and sporty and became a teen craze during its reign, forever solidifying the look between adults and teenagers across the country.  Although myself and Travis are wearing saddle shoes in brown tones, the traditional color way consists of a white upper accompanied by black saddle at the mid-section.

Joshua kissi, Travis Gumbs, Street Etiquette, Madras blazer, Madras, saddle shoe, Joshua kissi saddle, Bronx style,

Rugby Madras Blazer – Uniqlo Oxford – TM Trousers - Bostonian Saddle shoe

Fit Details : As many of you may know from the previous summer the lightweight fabric madras is a favorite of mine. Last time around I dedicated an ode to madras where I wore a pair of J. Crew madras classic fit pants. Now 9 months later they have been tailored and I can’t wait to wear them this Spring/Summer.  A slightly misfitting blazer  purchased from a friend has been transformed into my own liking with a bit of tailoring.
Street Etiquette, Joshua Kissi, Travis Gumbs, Saddle shoe

Photography : This time around we chose a slightly different path by working with San Diego native photographer Chaz Cruz . In this day where many can grab the label of being a Photographer, this gentleman actually embodies the hard work , vision and clarity of one. We decided to change up the scenery from our familiar background to the world famous Central Park: 843 acres of green, asphalt and concrete for all to roam through.
Travis Gumbs, Vintage Ralph Lauren, uniqlo pants, j.crew saddle, jcrew saddle shoes

Vintage Ralph Lauren ‘Vertical Stripe’ shirt – Uniqlo pants – J. Crew Saddle shoes

Jeremiah Nuamah , Jeremiah Joshua Kissi, Jeremiah Nuamah, Saddle shoe kids, kids saddls , saddle shoe kids, kids golf saddle oxfords, 50s saddle shoes

Left image – 1953 ||| Right image – 2010

Searching for saddle shoe images I stumbled across this image, apparently an Iowa resident by the name of Tom Alex back in 1953 on his first day of kindergarten and around the same age as my nephew Jeremiah. Intriguing to see 57 years later and 4 years late of their 100-year anniversary the saddles are still being worn. Simply a perfect example on how history repeats itself time and time again.


Have something to say?


  • sssence

        posted on April 5 , 2010 :

    Great post! Love my saddle shoes and have been rocking them quite a bit lately. As always, the historical aspect is informative and really helps to develop the post. Can’t wait to see what the rest of Spring/Summer has to offer!

  • Christine

        posted on April 5 , 2010 :

    Love the saddles shoes you’ve spotlighted above. I lived in my white and navy ones as a kid but haven’t owned a pair since. I think it’s time to sport them again for Spring/Summer! Any suggestions for a good pair for women that aren’t chinsy?

  • Kevin Lanre

        posted on April 5 , 2010 :

    Loving this!

    I actually bought a pair of those white jeans Travis is rocking from UNIQLO the other day and have Josh’s oxford in quite a few colours.

    You guys just keep killing it and I’m loving it.


  • Coldsun

        posted on April 5 , 2010 :

    Nice Post…
    And good pictures… Its funny how Central Park has sooo many views, dope areas, and can look so different at times…
    The Saddle Shoes are cool too, I wouldn’t mind having a pair…

  • SB

        posted on April 5 , 2010 :

    inspiration to seek out those highly coveted JMonae inspired saddle shows..
    who knows? I might even “tightrope” a little in them..

    you two look great, as usual.
    Stay creative,

  • Sarah

        posted on April 5 , 2010 :

    Saddle shoes are all the rage this season, and I can’t wait to get my hands on a pair. I really like the trousers with the shoes.

    Passport Smiles

  • Will

        posted on April 5 , 2010 :

    I’m loving the J. Crew shoes, Bass also has some good ones. I’m also loving that old Ralph Lauren shirt, its so bold but excellently classic.

  • wale

        posted on April 5 , 2010 :

    Great write up, looking at old images of Josh brings a slight smirk to my face because of the hair, never cut it cause it will be weird for us all lol.

    That Vintage Ralph lauren piece shows why the man deserves respect, timelessly appealing.

    what I consistently enjoy about SE is the knowledge that is always dropped about the item, the history or an interesting fact never hurts and you always deliver.

  • Meji

        posted on April 5 , 2010 :

    Cool stuff man. I agree with Wale – each piece has a little bit of history to it. I like how y’all always post that extra information.

    Keep it going my brudda. One love.

  • DesertNana~MB

        posted on April 5 , 2010 :

    You gentlemen are a true class act
    While most fashion makes my eyes cross or looks and feels out of reach, you offer beautiful timeless examples
    of how eco friendly fashion can stand beautiful among( i dare say above) the rest
    wonderful photography !


        posted on April 5 , 2010 :

    @sssence: Thanks Nicholas definitely a shoe that can be worn all around when the outfit meshes with it flawlessly. For spring/summer just expect the unexpected a bit a wow factor to things lol you know we like keeping secrets!

    @Christine: Nice a white and navy pair sounds great for all seasons especially being a female you have just so much more options to pair it with. I’m looking across the internet right now for you i’m seeing variations in the saddle shoe fused with a heel – check THIS SELECTION and let me know how it goes. I might purchase a pair for my younger sister

    @Kevin Lanre: Thanks kevin the support from our brothers across the pond is always appreciated trust me – next time you come to NYC we have to put something down on paper to do!

    @Coldsun: You’re right technically it isn’t the most largest park in the world but its pretty big to me we walked around a bit to find a good feel for the photos but really stayed in one vicinity of the park without straying too far lol.

    @SB: Funny you mention Jmonae when starting this post thought of her as far as artist even Elvis . She does the look great everytime clean with saddle shoes nice. and thanks

  • Kevin

        posted on April 5 , 2010 :

    That blazer is crazy!

    Regarding you saddle shoes Josh, any idea where I can purchase them on the web?

    Thanks a lot and keep on pushin’

  • [...] Read the full post over at Street Etiquette HERE. [...]


        posted on April 5 , 2010 :

    @Sarah: Definitely right and it should not just be ‘this season’ I would wear them for years on end lol

    @Will: Very true bass does produce some nice saddles -we have been knee deep in just old bold print shirts definitely great classic pieces! cant wait to break out others

    @wale: I know even myself i look at the pictures and say whoa I did look a lot different if I do cut my hair there will be no warning lol just a new post on the site rofl – which I highly doubt though for now. Thanks a lot always rely on this quote myself

    ‘History is important as it gives us the ability to trace back what has occurred previously to help us better direct ourselves to the future. ‘ – se

    @Meji: Thanks Meji probably one of our first readers on here lol atleast first ten appreciate it.

    @DesertNana~MB: No problem at all this is where the bold boundary of fashion and style lies , once think the two as the same definition that is. What we do here applies more to style but of course we’re all students of fashion! lol


        posted on April 5 , 2010 :

    @Kevin: The specific ones i have are vintage forgot to mention that in the post but here’s a good list of saddles to choose from

  • Kevin

        posted on April 5 , 2010 :

    Thank you Josh! Bien à toi

  • Reggie

        posted on April 5 , 2010 :

    Nice fits guys, the blazer is definitely better fit for your style after tailoring. I actually want that shirt Trav is wearing…like really bad! Saddle shoes seem like a timeless piece of footwear, the brown hues are def. a nice change from the b/w i’m used to seeing.

  • Afees

        posted on April 6 , 2010 :

    Aahhh Well Dressed and Intellectual. I wish to be just like or maybe better than you guys.

  • Birdfeed

        posted on April 6 , 2010 :

    Anyone know where I could find a pair that is vegan (i.e. non-leather/suede unless synthetic)? I’ve had a really difficult time finding a pair. The closest thing I’ve had to settle with are zig zags but they are all one sold color and pretty cheap materials.

    Thanks for the great post, by the way.

  • demilade

        posted on April 6 , 2010 :

    Nice RUGBY Blazer Boss FIts Nice Too

  • janeeyre

        posted on April 6 , 2010 :

    Great post. When is the Genesis of Style project coming out. Can’t wait for it.

  • Anonymous

        posted on April 6 , 2010 :

    Great post! Love your shoes!

  • David

        posted on April 6 , 2010 :

    Never cease to amaze my logic guys. I am possibly the biggest fan of Saddle shoes, but don’t own any. I know you are probably wondering why that is and it is because I have yet to find a affordable enough pair yet still the shoe be able to define me. If that makes sense, I need a pair of those in my life. The can make a plan fit pop if you apply them right, Of course, you two gents know that already. Particularly I am found of the suede and leather combo that you both have on, but to me nothing beats the OG Black and white classics that Miss Janelle Monae always has on with her tuxes. Any who, this post I could have seen as a Fall post seeing as those are a great fall item, but you nailed it right on the head with the title. Ha Until you respond.


  • Jonathan Morris

        posted on April 6 , 2010 :

    2 Truth which shall never be unfounded: Clothes make the man, and shoes make the outfit.

  • Lucas

        posted on April 6 , 2010 :

    That Madras Blazer is sick Josh. Shoes are on point too.

  • joseph A

        posted on April 6 , 2010 :

    i don’t know why but i’ve always confused saddle shoes with bowling shoes, thanks for the clear up, and do you guys work with multiple photographers or do you usually shoot your own pics?

  • Mark C.

        posted on April 6 , 2010 :

    Great post.

    I’m really diggin’ that blazer, by the way–the lines, colors and cut is spot-on. Very nice…

  • Kadeem J.

        posted on April 6 , 2010 :

    As a kid I always use to frown upon having to wear my saddle shoes to school and church. However, little man is killing it in the photo!… a style icon in the making…wait until he gets older

    Great post as always bruhs

  • Aaron

        posted on April 6 , 2010 :

    could you link me to those trousers? how are they so slim? they look amazing.

    also any links for mens saddle shoes in the UK?! reccomendations?

    you’ve really inspired me to get a completley different look for summer now. :)

  • Birdfeed

        posted on April 7 , 2010 :

    I was wondering the same thing as Aaron about the trousers. I can’t find any that fit me right anywhere. Link or info please?

  • Mister Anderson

        posted on April 7 , 2010 :

    Clean fits gentlemen. Both pairs of saddle shoes are quite appealing & I’m loving the contrast of your jacket Mr.Kissi.

  • SwanDiamondRose

        posted on April 7 , 2010 :

    hate to break it to you but you two might just be really big nerds ;) that being said i love saddle shoes too. and have been looking for a pair for a while. i love that madras blazer too. and so fitted. love that.

  • CAS

        posted on April 7 , 2010 :

    Another great post guys! I love how you incorporate vintage pieces into your looks and they still come off as modern and contemporary with the cut and tailoring of the garments. Great Job!

  • Style Odyssey

        posted on April 7 , 2010 :

    I read this as I’m wearing my J. Crew madras mini skirt from a couple seasons ago!
    Saddle shoes- what a classic. Love the second pair especially, in brown on brown. Gorgeous pair.

  • akaCola

        posted on April 8 , 2010 :

    great post! always educated when coming to your blog, love the saddle shoes and also that blazer looks great on you!

  • PeezoMTF

        posted on April 8 , 2010 :

    As usual, great post. The Saddle Shoes are dope, but @JKissi the Madras blazer fam?? You impressed me with that one. I’m from a the South and the coast, more specifically and I’m used to seeing businessmen gettin on yachts at the harbor and you really brought the summer aspect to the post. Don’t get me wrong…..I love the Saddle Shoes, but the blazer is doin for me…..much props and thanks for the continued inspiration


  • [...] Read about the Saddle shoes, the classic American fashion fixture that keeps coming back. read more [...]

  • Ashley

        posted on April 8 , 2010 :

    Just discovered your site via GQ and I’m instantly hooked! So inspirational! You guys have great style and your blog has a beautiful aesthetic. The saddle shoes are so refreshing.. makes me wanna buy a pair! :)

    much love


        posted on April 9 , 2010 :

    @Kevin: No problem at all.

    @Reggie: Yeah , when I received the blazer it was the right size but it didn’t fit me how I wanted it to , that being important when it comes to proportions of a outfit and all decided to get it tailored more to my fit, and of course pablo did a amazing job. Funny thing is I like the white/navy or black/white more than the brown hues maybe its just me

    @Afees: Thanks a lot, I’m sure you will create your own path my brother

    @Birdfeed: I have been looking around but no luck on finding it without leather and such but like you said zig zags have questionable quality ..

    @demilade: Thanks to you of course thanks again , I knew I wanted to buy something madras so when you told me about you selling it – I agreed to it lol asap – jacket fits completely different from when you had it lol

    @janeeyre: It should be releasing soon – hopefully. thanks lol


        posted on April 9 , 2010 :

    @Anonymous: much thanks

    @David: Countless brands make great quality saddles for a reasonable price it really comes down to what color or material o you want either all leather or suede nubuck. Well maybe I exaggerated on countless lol but Bass and a few other brands make some great saddles , I hear you on the white/black classic leather shoe it just gives off a much cleaner look even if you decide to beat them up or something.

    @Jonathan Morris: Very true!

    @Lucas: Thanks a lot man

    @joseph A: We usually shoot our own pictures unless stated so , this particular post was shot by our good friend Chaz Cruz did a amazing job but yeah the last post and the others before it was all shot by either me or Trav.

  • Jeneen Nicole

        posted on April 9 , 2010 :

    No one on the corner got swagger like yall!! Tres Chic as usual

  • Steve

        posted on April 9 , 2010 :

    I would rather go barefoot.

  • Abu

        posted on April 10 , 2010 :

    I Love Oxford shirts!!! That shirt Trav has on I want so bad. If it is Ralph Lauren I have to get it.


        posted on April 10 , 2010 :

    @Jeneen Nicole: Thanks a lot you have a lovely blog – ladies check it out !

    @Steve: That’s fine my brother

    @Abu: Yup its vintage RL so it would be difficult to find to be honest but I’m pretty sure you can find something similar thrifting

    @Mark C.: Much appreciated bro – madras is a great fabric hard to pull of sometimes but great

  • Kelly

        posted on April 11 , 2010 :

    WOW, AMAZING STYLE. I love the curly hair. Great oxfords!! Damn, there is nothing like a well dressed guy!!

  • Brick Callahan

        posted on April 11 , 2010 :

    I mentioned it elsewhere, but it’s interesting how the few spring looks you guys have put out early in the season are giving off ’90s vibe. The shirting, in particular, has a real recent throwback feel to it.

    Liking the shoes, even though they don’t really fit in my own wardrobe right now. It’s nice to see them making something of a comeback. Not to seem like a shill, but I just wrote a piece about how Steve Urkel was quite the trendsetter when you think about it. That includes him always rocking the saddle shoes. Check it out:

  • Sidney

        posted on April 12 , 2010 :

    Looking great love the madras blazer with the chino and… those shoes….def. a nice addition for the summer but…Please don’t button up all the 3 buttons on that blazer ;)
    greatings all the way from Germany

  • Ice

        posted on April 12 , 2010 :

    Hey Josh,

    I gotta quick q.
    Are the high top sebago’s that you’re wearing in the Complex spread the same as the brown ones on Sebago’s website? (

    They look like a different type of leather. I checked davidz but they don’t carry anything cept the low tops.

    Thanks cuz

  • Williams Jay

        posted on April 14 , 2010 :

    great job as always fellas #applaud

  • JB

        posted on April 15 , 2010 :

    Hey Jkissi,

    In what direction would you direct someone (like myself) who would like to dress in a more classy way as demonstrated by yourself and Travis? Did you guys learn from books or simply observing? I am really interested in becoming well-spoken as well as well-dressed.



        posted on April 15 , 2010 :

    @Kelly: Thanks!

    @Brick Callahan: I think you are one of the few people who have seen our influence/inspiration of earl 90s bold symmetrical patterns incorporated into our fits. It’s just so many great color palettes out there to mix with and incorporate into your own style whether that is more loose fit or slim. Nice post on Steve, i mean in his own respective right away from all the comedic references to him he wore suspenders / cropped trousers / etc lol he did a pretty good job in my honest opinion i agree lol .

    @Sidney: Hey , buttoning the 3rd button on a 3 button blazer isn’t bad in the particular picture for the critiques that I would get is the blazer looks a tad bit too tight lol – it’s all fun though greetings from NYC! nice Germany

    @Ice: Yes those are the same ones maybe their picture editing process may have altered one of the images but yes they should be releasing very soon under either david z x sebago or Ronnie Fieg x Sebago they fit pretty well and quality! very soon though my brother


        posted on April 15 , 2010 :

    @JB: Hey JB , I wouldn’t say books just the meshing of different inspirations myself and Travis contain – I would suggest emailing us to answer such a question in full. thanks for commenting though I know you ‘it’ though.

  • vpm

        posted on April 15 , 2010 :

    I found this site through GQ as I am sure many others did recently. I’m really surprised that it isn’t updated more than a couple times a month. No point in returning with any regularity to see the same stuff.

  • Stephen

        posted on April 15 , 2010 :

    Where is it even possible to get those shoes? They seem very historically American so I think finding them in Europe could be a feat to contend with. . .

    Keep up the inspiring blog.


  • Obiageli

        posted on April 15 , 2010 :

    What you gentlemen have going here is truly remarkable! What a great sense of style! I was referred to your site by a fellow blogger. Keep up the good work and post more often-(if it’s not too much to ask-lol).



        posted on April 15 , 2010 :

    @vpm: I hear you my brother we had a core audience before GQ and will after at the moment – jobs/schools/personal life could conflict with the time but as soon as school lets out you can bet you will see more updates ! We’re working on this currently this isn’t a magazine where you receive post everyday but we’re working on bridging the need – Thanks for dropping the comment

    @Stephen: Even though their history stems from American roots I don’t see any reason why you can’t also buy them via the internet and maybe a in store location if you searched – here’s a link to some shoes

    @Obiageli: Thanks a lot man – bloggers showing bloggers love is what it’s about great – tell that person I said mich thanks!
    BTW like I said above lol we’re working on that

  • Ice

        posted on April 15 , 2010 :

    @JKISSI: Good looking Josh!

  • vpm

        posted on April 16 , 2010 :

    Everyday my browser opens up with three websites: GQ, Gilt Man, and now you.

  • Ashlyn

        posted on April 18 , 2010 :

    I love saddle shoes!
    And everything about this blog.


        posted on April 20 , 2010 :

    C’mon its been awhile boys, keep us up to date here!

  • MarcoBerlin

        posted on April 20 , 2010 :

    Dear Street Entrepreneurs,
    just stumbled over your blog after being at university all day.
    I love your blog so far and especially like your newest post about the saddle shoes.

    An all time classic newly interpretet. Just tried to find them on a German website or somewhere on the web in Europe. I am blogging from Berlin and have not seen this model here. Unfortunatelly!

    Keep postin on this high level!

    Besides, are you wearing collar pins from time to time? I am also trying to find some in Berlin to enhance my wardrobe. I’d love to see you combining them. I have also posted something on collar pins in my blog, related with some old pictures found on the web! If you guys dont mind I have named my accessory posts also accessories are a neccessity. I just thought this perfectly expresses the sense of accessories.

    I am trying to focus more on men fashion on my blog too but I just started posting regularly. Trying to make blogs more important in Germany.

    Best wishes from Berlin,


  • Kristopher

        posted on April 21 , 2010 :

    Nice post gents. Of course I had to go get my first pair of saddle shoes after reading this. Still waiting for them in the mail as I bought them off ebay but I hope they turn out alright. Thanks again for the inspiration.

  • Oswaldo Sanchez

        posted on April 24 , 2010 :

    The shoes are okay.

    The MADRAS blazer is outstanding. It opened my eyes to a whole new world. Thank you.

  • DinTX

        posted on April 25 , 2010 :

    you guys are great – i just dropped by here from the Penny Loafer post and found this saddle post… We just got my 5yr old some some Bass Blk/Wht Saddle shoes… the first time he put them on (sans socks) he was in his jammers and did a crazy dance of some sort which killed me – skinny ass legs and big saddle shoe’d feet moving all crazy! now he wears them all the time and always makes a style statement – not many people can pull off Saddle shoes and Dark Blue Overalls (w/white T) but this little dude can… just waiting for the TX Heat and he’ll be in them with shorts… He also will kill it with just a button down and khakis if he’s heading to the grandparents… My boss at works says these give her nightmare from going to an all girls catholic school… guess thats another way to look at it??? later, DinTX

  • sikiru

        posted on April 30 , 2010 :

    Joshua… Damn, is that a moose knuckle I see? ease up bruh

  • admin

        posted on April 30 , 2010 :

    @sikiru: Rofl , ease up off my private part

  • deadpoetssociety

        posted on May 1 , 2010 :

    Hey guys, do you know by any chance where i can find those jcrew saddle shoes? Jcrew doesnt seem to carry them anymore, and i really like that color scheme. Any other brands carry similar saddle shoes?

  • We Shall Overcome...In Couture!

        posted on May 3 , 2010 :

    When I was a kid, I LOVED saddles shoes! It was the only style I would wear.

    Thanks for trip down memory lane!


  • [...] stepping a bit out of your comfort zone here.  Don’t limit yourself to sneakers – saddle shoes are a bit dressier but infinitely more stylish and if taken care of will last decades and draw [...]

  • [...] Consider stepping a bit out of your comfort zone here. Don’t limit yourself to sneakers – saddle shoes are a bit dressier but infinitely more stylish and if taken care of will last decades and draw [...]

  • The Ca$h

        posted on May 25 , 2010 :

    Great Post Kiss
    Forget about the shoes
    That entire suit looks amazing… well put together.