What It Was Like Shopping for Clothes in Market Square 100 Years Ago

By Laurie Stein, The History Center of Lake Forest-Lake Bluff

In the earliest days of Lake Forest, clothes shopping meant buying bolts of cloth at James Anderson’s general store on Deerpath or stocking up on dry goods down in Chicago. Outfits were handsewn at home or designed by a custom dressmaker or tailor. 

By the 1920s, mass-produced clothing, mail-order catalogues, and the emergence of big downtown department stores like Marshall Field & Company had transformed the clothing retail landscape. As off-the-rack shopping began, several local specialty shops arose around Market Square during that decade that focused on tailoring pre-made clothing, offering popular brand names and the latest trends from Europe close to home.

The store now known as The Lake Forest Shop opened in 1922. 

Mayer Kubelsky was a Russian immigrant who came to Lake Forest in 1918 and opened a shop which sold fine men’s clothing and accessories. After Kubelsky’s previous store in Waukegan went bankrupt, he forged a new start by drawing on previously untouched funds sent by his son Benjamin -- who was better known as Jack Benny. Benny was then an up-and-coming vaudeville performer but was on his way to becoming a top comedian, actor and national figure.

Benny often visited his father and sister in Lake Forest and would occasionally sign autographs at the store, located at 264 Market Square. Mayer Kubelsky ran the business from 1918-26 before his son-in-law Leonard Fenchel took over. Until it closed in 1934, the shop was the local purveyor of Kuppenheimer high-end menswear, a firm which also had Lake Forest connections – executive Jonas Kuppenheimer had an estate on Green Bay Road.

Next door to Kubelsky in Market Square was Garnett’s, which supplied dry goods to Lake Forest for over 50 years in the mid-1900s. J. B. Garnett & Company was founded in Highland Park by Joseph Garnett and later run by son James. Garnett purchased a Lake Forest dry goods shop, Meyer & Co., in August 1921 and expanded its business to 270 Market Square.

The shop offered a variety of ready-to-wear clothing, including blouses, skirts, sweaters, stockings, ties, socks, underwear, pajamas, trousers, and shirts. Its policy, according to a 1921 newspaper article, was “small profits and quick turnover.”

Over the next five decades, Garnett’s expanded in size and in product lines into a large department store, offering apparel, home décor, accessories, and bedding. It closed in 1973 in Lake Forest and six years later in Highland Park.

Across the way in Market Square, another new shop opened in the 1920s, catering to women. Margaret Baxter Foster founded The Sports Shop in 1922 as a creative outlet for her passion for collecting fashion on her travels. Many of her pieces were sportswear separates, a whole new way of dressing. The Sports Shop took over the iconic half-timbered façade at 265 Market Square.

Women came from all over the North Shore to the store, later known as The Lake Forest Shop, to purchase beautiful clothes and accessories—cable-knit sweaters, cashmere cardigans, plaid slacks, challis nightgowns and robes, clutch handbags, coats and evening gowns for all occasions. The shop also carried special items for holidays such as hats to wear in the Easter parades that took place in Lake Forest and Chicago.

Robertson's offered fine men's clothes for decades. Around the corner on Deerpath was a new option for menswear that became a longtime staple. In the 1920s, George Robertson and Walter Smith discussed opening a haberdashery together in Lake Forest. Robertson was financially prepared first and opened Robertson’s in 1922 (15 years before Smith’s Men’s Store, in 1937).

The location of Robertson’s was 279 East Deerpath. The shop quickly became known for its fine men’s clothes including silk foulards, cashmere mufflers, leather gloves, madras coats and shirts, and all-wool sport shirts and robes. For over 70 years, until it closed in 1993, many men remember fondly visiting Robertson’s to purchase their first navy blue blazer or renting a tux for prom or a wedding.

Find out more about these shops of the 1920s as well as others at the History Center’s exhibit “A Window on Fashion: The Evolution of Retail Clothing Around Market Square,” open through April 4. Find out more at www.lflbhistory.org