Who Wore it Best: Olive Leather Wingtips

September 11th, 2013

I beat the guys so badly in our latest “who wore it best” post, that I thought I should offer them a rematch asap.

It just so happen that our friends at Johnston & Murphy were looking to hook-up the Articles of Style crew with some new kicks for Fashion Week, so Towni, Wes and I looked through their latest collection and agreed on a pair for our next challenge… We all love a good wingtip, especially one in an unexpected, but still versatile, color. Therefore, we went with the Tyndall wingtip in olive leather.

Feel free to vote for your favorite outfit, and tell us why (or why not) in the comments!

    1. Dan – Tropical Tailoring


    This is officially the first look published from our new home in Los Angeles.

    We shot this in our backyard (Alex and I are sharing a house) and, yes, we have a backyard! Complete with our own fruit trees (oranges, bananas, avocados, pomogranates, all that). As a guy from Canada who’s been living in manhattan for the past eight years, I’m excited for a change in lifestyle…not to mention the changes coming with our site, content and business… More on all that soon.


    I’m still figuring out my LA style, so for this “who wore it best” I thought I’d stick to what I know best: seasonal tailoring.

    Had to go with the tropical inspiration: unlined linen suit, flowy raw silk shirt, and a classic Panama hat. The brass and gold touches give it a little edge and compliment the rich green of the shoes.


    These olive leather wingtips are more versatile than you might think.

    My favorite things to pair them with: khaki chinos, washed jeans, light grey trousers, tan/brown suits.


    • Natural 100% linen suit
    • White linen/silk henley t-shirt by Theory
    • Brass railroad spike ring by Giles & Brother
    • “Stella” Watch by Brera Orologi
    • Slim brown leather belt Vintage
    • “Tyndall” olive leather wingtips by Johnston & Murphy

    2. Towni – Weekend Grungy


    Towni took a casual angle, repping his new home in Brooklyn with a grungy denim-on-denim look. The only time the guy wears a suit anymore is when he’s working his new gig at MAB!

    Either way, he offsets the denim washes like a pro, while subtly pulling together the greens of the shirt, belt, and shoes.


    Towni has really got me thinking about growing my hair out – especially now that I’m out on the West coast.

    I think the long hair, and the Samurai bun (as he calls it), really suits him. With the beard it gives him a slight “grungy” character that offset his usually very clean, preppy style.


    It’s also worth mentioning how comfortable these shoes are!

    Their cushioned insole, leather lining and rubber sole make them noticeably more comfortable than a lot of wingtips…which is especially noticeable when you’re in the business of wearing shoes fresh out of the box, without socks.


    • Denim jacket by Levis Vintage
    • Red/Green Plaid shirt by JCrew
    • Faded black jeans by J. Crew
    • Aviator shades by Randolph Engineering
    • “Tyndall” olive leather wingtips by Johnston & Murphy

    3. Wes – Original Gangster


    Wes went full-out 1920’s gangster with a mean double-breasted suit, club collar shirt and  retro paisley tie. Call it rum-runner-chic.

    This is one of those outfits, and photos, that represents the beauty of timeless style. For example, check it out in black & white; without context it would be very hard to determine the year/decade/era.


    I have a feeling we’re going to get a lot of emails about this beautiful Ariston cloth suit…

    Don’t forget, Articles of Style readers get 10% off their first order at Michael Andrews Bespoke.


    The olive leather almost looks brown, but stands apart just enough to catch the eye.

    Of course they’re sharp enough for a business suit, they’re dressy wingtips after all.




    Thanks, as always, for reading.

    Yours in style,

    Articles of Style


    Photography by Alex Crawford

    • Cass

      Dan: I love linen suits but I feel the way you put this together is very forgettable.

      Towni: Forgettable. Nothing about this look says you actually like clothes.

      Wes: Rum runner chic! Love it. I really love this classic look. However, my few critiques are: I think the jacket could be a bit more tailored to the body because it looks a bit wide in the first pic (it could just be the way you are standing). A double breasted suit should only be open when sitting down. Hem is too high…let them down. Only loafers can handle a high hem. Lace-ups with a high hem only reads ill fitting high-water pants.

      *Dress like you are meeting your worst enemy today!

    • Hugh

      Towni, loving the grungier style and the samurai bun is badass!

    • kieran

      Where did you get that shirt??

      Why can I never find shirts like this in Australia.

      Please help a man with no style.

    • JB

      Thanks for posting this guys, ya’ll definitely got me over the fence to getting these. I just got my pair today in saddle tan. I think it’s awesome how each of you took the shoe and interpreted its shape and color into your own very unique styles. I’m seriously digging your suit Dan, it looks mad comfy. Towni, inspiring stuff, I saved the picture for reference on how to remain comfy whilst killing it. Wes, lookin like a straight OG, badass.

      BTW, after seeing the Tyndalls on my feet, I can’t help but think they’re about an inch too long from my toes. I sized down after reading amazon reviews saying the same thing, “too long”. But even after sizing down, I still feel that they’re too long while the rest of it fits perfectly. I’m not sure if I’m just unaware that this is simply the style of wingtips, or J&M just took this approach with these shoes. Did any of you find yourselves thinking the same? Your feedback would be much appreciated.

      My first comment, but I’ve been reading for nearly 8 months now.
      I just want to say, your site has changed my perception of personal style, and ya’ll keep me coming back for inspiration every day. Best wishes to you with the coming changes!

    • Jonathan

      Something out of the box for Towni well done.

    • AA

      how tall is wes? he usually looks quite small in other posts… probably due to his build..but thats also maybe why everything looks sharp on him

    • Mike Saltz

      Dan – who is that gold bracelet by?

    • AGT

      Glad to see you smiling, Towni. Wes- keep your hair, its perfect for everything other than playing ball.

    • http://urbsuburbstyle.com/blog/ Paul

      Love Dan’s look, and love the suit. Welcome to the west coast!

    • Shannon Roberts

      Towni’s hair is awesome.

      • http://www.tsbmen.com Westley Dimagiba


    • Joe

      All the looks are great and I really like the shoes, especially that color. An irrational pet peeve of mine is black soles on brown shoes, whether the soles are rubber or not. The dark rubber soles here however go well with the unconventional olive color. I voted for Towni, but it was certainly close.

      Beautiful suit Wes, however I remember reading this great blog once that said “leaving a button or two unfastened at the end of your jacket just to show that you paid alot for it, as many wall-street types do, comes off a little…” now what was the word he used… I don’t recall (though that same blogger went on to say he still leaves them unbuttoned sometimes, oh well http://mensstyleblog.blogspot.com/2009/08/tip-of-day-open-up-your-cuffs.html)

    • Mike88

      Towni, you’re rocking the jean jacket and the tied up hair. Do them both more often. Hot.

    • Anonymous

      Towni, you need to both, tie your hair up like that and wear that jean jacket more often. Looks amazing.

    • Toronto

      Finally I can vote for Towni. Amazing. It all looks great, including the elastic.

    • Sean

      A rubber band to tie back your hair? Really? C’mon man! Not only does that hurt, but it looks bad

    • Pete

      I think Wes forget to button his shirt and jacket cuffs.

      • http://www.tsbmen.com Westley Dimagiba

        knew I forgot something…

    • Stuart


      Is that a La Matera belt? Regardless, I love the addition. Killing it.

    • Jaime B

      Yup, gotta go with Dan on this one, that linen suit paired with the barely olive wingtips is just too tight of a combo. Oh and Dan, happened to be perusing highsnobiety.com and the TSB crew showed up in one of the slides for NYFW street style, slide 26, the crew re-united (minus Towni)!

    • Kojo Y

      Everything about Towni’s looks is simply dope. What stands out most to me is the tribal print belt and the pony tail hair makes the entire look come together. DOPE!

      • Kojo Y

        And sadly to say the other 2 looks just look corny. Sorry guys

    • http://sentenceaday.com Mitko Karshovski

      Im going to go with Towni on this one because I love a denim jacket and the long hair is badass (dont let anyone tell you its not, they are just jealous. With that said though I love Dan’s look, I have a soft spot for linen suits but that hat is too wide for me…im not balsy enough for that haha.

    • Tyson

      Dan, growing your hair out would be great, but with your hairline, I think short hair would suit u better. Just my opinion bro, either way, you would rock it well fam!

    • Joe

      Finally! Wes in a suit jacket where he doesn’t push the sleeves up to his elbows like a middle-schooler at their first summer dance. Going with Towni, however. Not the biggest fan of the shoes, definitely wouldn’t describe them as “refined”, as is stated in the article.

      • http://www.tsbmen.com Westley Dimagiba

        so I’m not allowed to push them up if I’m dancing?! Crushing dreams over there.

    • John B

      Going with Dan. The background is pretty good too!

    • http://wacavenue.blogspot.com Theguybehindthelens

      Dan’s look is so effortless. The seasonal fabrics are perfect. The hat literally tops everything off in just the right way.

    • http://machinemotel.tumblr.com Michael

      I think it’s a three-way tie! You all look great. Are the shoes available in J&M stores yet?

    • Brooks

      For the longest time, I thought Towni’s long hair looked awful. He’s come full circle, though–rockin’ the samurai bun, man. He gets my vote, although you all had great looks today!

    • Hai

      Are you staying in LA for awhile? I’m curious of what would be practical style for these hot days

    • http://www.thewrittenrunway.com Ambyr

      I love that you showed how the shoe could be interpreted into three totally different styles. Love wingtips!


    • http://thekacar.com theKacar

      Dan got this. But Towni holding it down with the hair!

    • http://www.twitter.com/iPodschun Derric

      Voted Towni.

      Dan and Alex, welcome to SoCal. East coast “summer suits” can work for three seasons down here.

    • http://undefined mathieu lavoie

      Towni is killing it today!

      Looking very manly, yet well put, and (did I dare to say it?) very sexy! ;-)

      Good job sir

    • LouCaves

      Everyone looks good. I’m feeling the casual today so i went with Towni.

      Looking better today, Wes. I hope the ice cubes helped. LOL!

      Thanks, TSB.

    • cam

      towni with one of the most stylish looks ive seen in awhile…on some indiana jones in the city vibe

    • Brady P

      3 solid looks, but OG Dan takes it for me. He just looks so comfortable in that suit. Excited to see what’s to come

    • Steve

      Towni wins it especially with that Samurai bun, it rocks!! I think you guys are already starting to look too “LA” for my taste though.

    • Chad
    • Harvey

      Please bring some of the East Coast style to Cali. Living in Cali but repin’ the other side.