The Kiltie Loafer


Old Fashioned renewed. Ah yes, those weird looking shoes that your retired investment banker Uncle Bobby wears to cocktail hour at the country club bar overlooking the putter’s green. The Kiltie Loafer – one of the last untouched frontiers of preppy resurgence! Everyone had to get the penny loafer, then the tassel loafer, sure why not a venetian, ok maybe a fourth pair of strap or pinch, but hardly anyone ever thinks of the Kiltie, which as you can guess pays ode to our bare-legged Scottish friends. I remember my awakening as a Campus Pervert, during my first day as a freshman walking to my first lecture ever.

A guy walked in the opposite direction in sunglasses and croakies, nanny red 5″ inseam shorts, tucked in white OCBD, and kilties. His hard soled loafers clicking on the brick sidewalk traversing the quad. He also had an Elon The Game College Bar hat, so I assumed he was just taking a few classes at my cheaper public university to fulfill some credits for his future nearby alma mater (made sense since my school was more known for the liberal arts than for finance and law…) I reacted just as how the uneducated masses would, thinking he was douchey and whathaveyou.

That was in the midst of my Abercrombie days afterall. But the image stuck with me, and for all I know it unconsciously pushed my curiosity into the style, having seen what “True American Prep” actually was, far surpassing the authenticity of any faded A&F muscle ringer that I preferred in those days, and now leading to me writing these very words today.

Forgive the hopscotch down memory lane…back to the topic. Traditionally, my official stance with the Kiltie is that its too oldschool, and perhaps they haven’t become popular even in the neoprep-obsessed runway fashion of today for a reason. But I’m starting to change my stance to the kitten crawling on the fence. Typically people will say it’s on the wrong end of “grandpa style”, as in, they’re actually what grandpa wears right now. Dapperd alluded the Kiltie loafer as unwearable by anyone under 50. Which is uncool and unhip in that connotation. Because lets be honest, it’s somewhat of a fugly shoe. Lots of going on when you add in the additional tassel or leather shoe string. But because they’re so gnarly and out there, and particularly since the fashionably inclined have starved off so far, a young man sporting them barefoot in the summer with a careless attitude automatically make them ultracool. Ultra TFM. Just as the gentleman imprinted in my memory, it leaves a mark.

So I wouldn’t wear them for it’s intended purpose. All shiny and spiffed up at an alumni event. Quite the opposite. They would be strictly a beater shoe. An “I-really-don’t-give-a-flying-” kind of shoe. Scruff them up and ruffle those feathers (literally). Mister Mort had the right idea. Summer and Spring only. Barefoot only. Shorts only. That way you’ll not be mistaken as disgustingly old fashioned for the GTH aptitude you want to convey, combining the extremely happy-go-lucky short inseamed and the extremely broody Kiltie.


Not to be dressed up.

Only to be dressed down.

Don’t buy the nasty rubber or boat soled ones. Dockers, I am looking at you. I’m iffy about the wingtipped shenanigans too. The frills are enough “old man” as it is. Color wise, stay with a brown variation to be safe. Black tends to swallow up the off-beat.

Settle Down….No doggie!

CollegeTrad Recommends:

Allen Edmonds Woodstock and Cornelius in Chili. Made in USA. Two-toned colors kill the already surgically precise balance with what you’re trying to achieve with the Kiltie Loafer. You’ll want to swing that pendulum towards the nuanced.

Eastland Ellsworth in Brown or Tan. Made in Maine.

Bass Layton in Burgundy. This is the one you’ll have to put your groove on. Don’t polish it ever and let the grime lay waste. Look forward to haphazard marks on the sole and leather by the gravel you’ll walk on when you go trail hiking in it. Refer to Mister Mort’s tasseled loafers above.

Cole Haan Hudson in Woodbury Tan or Burgandy. Similar styling to above, but with a lighter color option if you’re feeling that way.

Gokey Kiltie Camp Loafer in Brown. A fusion with the camp moccasin, this one is the most casual you’ll go. I am almost hesitant to recommend this one, because the whole point goes along with taking the shine out of a formal pump, but these don’t look too departed. At least it’ll probably be the most comfortable out of the bunch. Doesn’t hurt it’s made in ‘Murica too.

If you absolutely, positively love the look of the wingtipped Kiltie, then make sure you wear them in a sartorially modern manner, and not with your baggy Chaps pleated khakis. In which case, go with the prime steak. Alden, which is rumored to have made the original tassel loafer, supposedly made a few kiltie wingtipped varieties as well. I can’t seem to find a retailer for a new pair at this moment, but you’ll be better off searching on eBay anyway (unless you want to spare a few hundred for a new pair of sh*tkickers!)

Rakish Style- Alden Kiltie Wingtips, Fun Socks, Raw Denim

I don’t own a pair of Kilties. Maybe I need to. Summer is just around the corner. Special shoutout to a faithful reader for the idea.