This post is a reprinting of a post on a forum that is frequented by Billax. Billax is not only one of my style role models, but a friend and a man that was Trad back when it was called Ivy League. If you have not read the other posts that I have reprinted of his I strongly suggest that you do: Uprising by Billax & Loafers by Billax

I first started noticing clothes as a HS Senior in 1958, when two of my college-attending cousins came home for family Thanksgiving. While one cousin went to Northwestern and the other to Cornell, they showed up for Thanksgiving in near-identical outfits: OCBD, Shetland sweaters (one a crew & the other a V neck), khakis, Wigwam socks and Bass Weejuns. I deduced a uniform for college attire. Since I was in the middle of college applications myself, I asked my folks for Christmas presents of “clothing the cousins wore.”

Once in college, I had the great good fortune to work in a Men’s clothing store that catered to the “Natural Shoulder” crowd. I learned more about men’s clothing from the proprietor of that store than I have learned since. I considered him a great mentor. He’d open up OCBDs from Sero, Gant, and Troy Guild and take me through the – often minute – differences among them. Stuck with me. It was his contention that “Natural” meant more than shoulders. Natural shoulders, natural fibers, natural (vegetable and insect) dyes all went together, according to my boss. I lapped up every distinction he threw at me. To this day, he remains the best teacher I’ve ever encountered.

In March of this year, my youngest son was accepted to his dream school – Yale. His Christmas presents reprised the requests I made to my parents more than 50 years ago. I hope the my gifts to the boy “take.” But, turning on the “way back machine,” here’s what was on my mind 54 years ago.

The Choices I made:
When I started getting interested in clothes in late 1958, I had to select shoes, socks, pants, shirts, sweaters, ties, sport coats, suits and outerwear in preparation for heading off to college in the Fall of 1959. Based on recollection, pictures from my photo albums from the time, and limited by a faulty memory, I propose to go through my preferences from 1958-1964 in every category of apparel. Here were the contenders in each category, from the bottom up:

Sneakers

All white was the only way to go in my High School and throughout my college days (1959-1964).

Converse All Stars: The company was founded in 1908 and has been a leading factor in plimsolls ever since. Their Converse Chuck Taylor All Stars and Jack Purcell tennies were legendary sport shoes even then. They soared in popularity in the late 1950s and ’60s, but never rivaled Sperry or Keds. Here’s the current Converse All-Star model:

College kid in Chuck Taylors 1960

Keds champions: US Rubber, now Uniroyal, created its iconic shoe, “The Champion” in 1916. Popularly known as the “sneaker,” Keds created a new category of footwear – a shoe so quiet you could sneak up on people! It’s been embedded in popular culture ever since. In four more years, the Champion will have been on the market for 100 years! Here’s the current “Champion Original” model:

College kid in Keds 1960

Sperry Sneaker Topsiders:  Sperry started making sneakers in 1935. They continue making them to this day. They became quite popular and their ubiquitous blue stripe around the top of the sole made them easily identifiable. In my circles, Sperry’s rivaled Keds for “most sought after” sneaker.
Van’s: Van’s didn’t come along until 1966, long after I’d made my decision to go with Keds. They were a part of the skate board phenomenon, but they were – and are – very popular. The company was founded in Anaheim, California and has always had a slightly “bad boy” vibe to me. I’ll admit that it appealed for that reason, but it was too late for me. I was a Keds guy. Here’s the current version of their original sneaker, the Authentic:

Which did I choose and why?
In late 1958, sneakers were just starting to be cool in my High School. I went to the department store and saw the Converse, Sperry and Keds sneakers. I chose the Keds Champions because:
• they had a slightly thinner sole, they were entirely white (no stripe)
• the eyelet layout looked more like a regular shoe than Converse. All in, they were more modest and minimalist. As one who finds the foot the least endearing appendage, I’m not inclined to dramatize it. For that reason, Keds were an easy choice.
Which sneaker became more popular?
In my circles, Keds by a smidge over Sperrys and by a mile over Converse! Vans wasn’t in business then. Still saw a fair number of Converse All Stars, but Keds simpler, slimmer, less decorated look was what the market wanted. These were among the first Unisex apparel categories. They were just as popular with girls as they were with guys. If someone told me I couldn’t wear Keds, I’d be OK with Sperrys. If I could only buy Converse sneakers, well, I’d give up sneakers entirely.

If I had it all to do over again, would I change?
Nope. Still wear Keds Champions – fifty four years later – probably once every ten days – more often in the Summer, less frequently in the cooler months.