Sneaking up on Summer

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Sneakers and summer are a natural pairing — memories of a brand new pair of sneakers post Memorial Day are imprinted deeply in our fashion psyche. Leaving the old ones at the shop, we would sprint down the street in anticipation of the new adventures of the upcoming season. Once the domain of athletics alone, sneakers through the years have become as ubiquitous as loafers in today’s dressed-down, athleisure-obsessed world.

In the late 18th and early 19th century the industrial revolution led to both mass production of goods, and workers with more free time to pursue athletic pursuits — in particular lawn tennis and beach bathing. The Liverpool Rubber Company, founded by John Boyed Dunlop, created the earliest sports shoes, known as Plimsolls, for the resemblance to the “Plimsoll Line” on a ship. It was a rubber sole with a canvas slip-on and left lots of room for improvement.

Early Plimsolls and their applications.

In the 1890s, Dr. Samuel Plimsoll invented “the Plimsoll Line” through an ingenious method of calculations and symbols; indicating the safe cargo line for ships in varying temperatures and predicaments.

Today’s Plimsoll, £39

Soon after, the Goodyear Company improved on the shoe adding ties to the design and the archetypal Keds were born. Kids of all ages sported the style.

Fun fact: They were called Sneakers for the ability to quietly sneak up on someone.

In 1924, Adi Dassler founded the company that would later be known as Adidas. The shoe was popularized by Jesse Owens at the 1936 Berlin Olympics as the first track shoe of its kind.

Converse Rubber Company began in Boston by Marquis Converse in the early 1900s. In the ’20s the company created athletic shoes specifically for basketball. Chuck Taylor, an enthusiastic semi-pro, reached out to the company to assist in redesigning and promoting the brand.

In 1969, Chuck Taylor was inducted into the Naismith Basketball Hall of Fame.

He hit the road to peddle the lace-ups to high schools and colleges; and pretty soon the entire NBA and their fans were sporting the kicks. Converse rewarded Chuck’s efforts by naming the shoe after him and adding his signature to the All Star logo. It was the first pairing of brand & athlete, but Chuck did not share in the profits. Instead he enjoyed a generous expense account and traveled the country in search of new accolades. It was his passion.

Wilt Chamberlain in an ad for Converse.

Since then, the ubiquitous style has grown in popularity and relevance as celebrities, star athletes and all of us plebeians embrace the brand.

Shop the Current Converse Pride Styles.

Tennis great and hall of famer Stan Smith dominated his sport in the ’70s. As a result, Adidas came out with an eponymous label. Its popularity continues today as an all-time classic in preppy style and a recognizable global style.

Stan was inducted into the International Tennis Hall of Fame in 1987.

Classic Stan

Kids Unisex  $65  /  Mens Original SALE $100  /  Women’s Original  $110  /  Men’s Original $150  /  Kid’s Unisex $65  /  Golf  $120

But these past examples were nothing compared to the frenzy that was created in the ’80s by Nike with their Air Jordans. This is the turning point when the modest athletic shoes crossed over into celebrity territory. The popularity of Michael Jordan catapulted the star and the shoe into the stratosphere of commercial success, spawning generations of fans eager to get their hands on the goods. Nike has kept the mystique alive by dropping new releases of limited quantities throughout the years.

According to recent research conducted by eBay, “Sneakers are not only a type of footwear but are a way to express yourself, your style and convey your personality. In fact, one in five respondents admitted that the sneakers someone is wearing can define your character. Whether someone views you as confident, alternative or friendly could rely on a quick glance at your footwear.” eBay sells a pair of sneakers every 1.5 seconds.

Men’s Nike Air Jordans on eBay $150

We discovered that the average person owns six pairs of sneakers, with 25-34-year-olds in possession of the biggest collections of nine pairs. With that kind of audience, no wonder that every luxury designer has thrown their shoe in the ring. Hilary picks some of her favorites and has styled them oh-so chicly for effortless elegance.

Hilary sporting her Skip & Lee, Personalized, $395

“I used to be an “only wear sneakers when working out” type of gal. But now, even I have succumbed to the trend of sneakers every day with everything. I love a retro or a classic look. Supergas worn by Kate Middleton are never out of style and I think Hogans are a great dressier sneaker option and they have a heel.  A white sneaker in the summer like Tretorn or the fun Skip and Lee’s that you can personalize, look super cute with everything from jeans, dresses or skirts.  But I have kept some traditions … and I will leave my Nike Runners and On Clouds for the days I hit the gym.”

First row:  New Balance Sea Salt With Atlantic  SALE $129  /  Golden Goose Superstar  $495  /  Autry Medalist In White And Fuchsia  $216    second row  Loewe Retro Runner  $690  /  Gucci New Ace Leather  $750  /  Superga Cotu Classic  $65  Third row:  Axel Arigato  Dice Lo  $270  /  Reebok Classic  $90  /  Veja Esplar Bicolor  $130  Fourth row: Axel Arigato White  $270  /  Skip And Lee Skips Personalized  $395  /  Hogan Interactive White SALE $381


Just this morning, my daughter Kell came downstairs in a pair of great looking knit sneaks. I discovered that they are Adidas Yeezy, Kanye West’s brand. He is one of a long line of rappers to jump into the marketplace including Snoop Dogg, Lil Wayne, and 50 Cent to name just a few.

Yeezys on Amazon. Various price.

Which brings me to the subject of “Sneakerheads” — fans who collect, trade and sell sneakers. Many of them don’t even wear them out of the house! Their website of choice is StockX. Here are their most popular sneakers in the last 72 hours.

The “athletic footwear market” reached $127.3 billion in 2021, according to Statista. Luxury fashion designers have come on strong, turning on the tap of this profitable market. Interestingly, Stella McCartney was an early collaborator with Adidas.

Adidas Stella McCartney, $126.

Anna Wintour & Vogue sneakers.

Adidas x Gucci Gazelle for men & women.

Dolce & Gabbana Grass Print; SALE $465.

Balenciaga, of course, is ahead of the pack, taking the style to new heights (and prices!)

Speed Knit Sock Trainer  SALE $597   /   Expander Spring Heel  Trainer  $1250  /  Defender Exaggerated Runner  $1090Track Clear Sole  $1090  / Xpender Colorblock Stiletto  $1290  / Track Lace Up Mules  $555  /  Track Hike Caged Chunky High-Top  SALE $892.

Recently Hilary and I played tourists in our own town at the Vanderbilt Summit. If you haven’t yet been, it is an otherworldly, joyful experience. In our own straw poll, about 90% of visitors were sporting some kind of sneaker (as the instructions recommended flat shoes).

As usual, Hilary wears it best along with her amazing Ala von Auersperg shirt jacket.

Hogan Interactive Beige, $495.

That same night, Martha Glass shared an instagram photo from London of her stylish son John Glass and daughter-in-law Roberta Benteler. You can follow Roberta, an interior designer, on piffi_be.

Trend Alert! Sneakers with dresses is a look that is here to stay as devotees rave about the comfort of the insouciant fashion statement.

No one, however, sports it better than our young friend, Olympia Serena.

Olympia in Millbrook looking so fresh. Notice the no laces look!

Whether you like it or not, sneakers are embedded in our American zeitgeist. So lace up, tie on, or strap in and pick a pair or two to sport this season and off you go in comfort and style.

In the immortal words of Nike: “Just Do It.”

Photos courtesy of US Open Tennis, Naismith Memorial Basketball Hall of Fame, Tennis Hall of Fame Newport, Rhode Island &  Library of Congress.

Karen Klopp and Hilary Dick are the Founders of We Take the Guesswork Out of Dressing, the Legwork out of Shopping and the Panic Out of Packing.™

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