What Is Chicago Ivy?
Ivy style, rebuilt on the South Side.
A Chicago answer to an East Coast look.
Chicago Ivy is a menswear style defined by WearWolfe. It takes classic Ivy dress and gives it an edge from vintage military, workwear, and jazz. Small batch. Natural fabrics. Made to be mended and handed down.
Chicago has always known how to dress.
The fashion world looked to New York and Paris. Chicago was too busy building, selling, and dressing the country to ask for the credit.
Harry and Max Hart open a men's clothing store on State Street. It grows into Hart, Schaffner & Marx, the largest men's clothing company in the country.
Chicago becomes the second largest center for men's clothing in America, making roughly 15 percent of the nation's output.
Chicago's garment workers strike, and the Amalgamated Clothing Workers of America is born.
Eunice Johnson of Johnson Publishing launches the Ebony Fashion Fair in Chicago. It brings couture to Black audiences for fifty years.
We stay Chicago.
This is a business city, and it dresses like one. We dress for the weather, and we know how to dress. Chicago Ivy is not borrowed from anywhere. It is ours.
Chicago was never part of the Ivy story. So we wrote it.
This is our story and our perception. The history comes from the scholars listed under Further Reading. The way we connect it to clothing is our own.
Ivy style began on East Coast campuses. Oxford button downs, wool sweaters, and pressed trousers became the uniform of a certain kind of American man. Chicago was left out of that story, even as it made the suits half the country wore.
Chicago Ivy keeps the clean collar and the tailored line, then adds the toughness of the men who built this city.
Between the 1910s and the 1970s, millions of Black Americans left the South in what became known as the Great Migration. Chicago was one of the main destinations. The Illinois Central Railroad ran north from the Delta to the South Side, and the Chicago Defender called families north.
They built cities inside the city. Bronzeville, Chatham, Woodlawn, Lawndale, and neighborhoods across the South and West Sides, each with its own churches, businesses, newspapers, and nightclubs. They came as porters, doctors, nurses, chefs, teachers, tradesmen, and business owners, and they dressed for the work they did and the lives they built.
Chicago Ivy honors that journey.
From the Delta to Chicago.
The Delta
Cotton fields and the hands that worked them. Where the fabric begins.
The Train
The Illinois Central, carrying families north with everything they owned.
The Work
Porters, doctors, nurses, chefs, teachers, and tradesmen. Every profession had its uniform.
The Clubs
South Side jazz. Ivy clothes worn with a style all their own.
The Neighborhoods
Cities built inside the city, on the South Side and the West Side. Where Chicago Ivy comes from.
Ivy is the base. These are the edge.
Vintage Military
Black American soldiers came home in wool overcoats and boots built to last.
Gives: StructureVintage Workwear
Every uniform of a working life: the porter's jacket, the chef's coat, the doctor's white coat, the tradesman's denim.
Gives: PurposeVintage Jazz
South Side musicians took the Oxford, the knit, and the trouser and made them their own.
Gives: SwaggerNatural fabrics only.
Fibers from the earth and from animals, never plastic. They breathe, they age, and they can be mended. This is the cloth of Chicago Ivy.
Raw Selvage
Fades to your life.
Wool
Lasts decades. Patch it.
Oxford Cloth
Softens every wash.
Corduroy
Wears like workwear.
Leather
Darkens with your hands.
Linen
For the Chicago summer.
Cashmere
Soft, warm, and lasting.
Merino
Fine wool, worn close.
Silk
Lines the coat.
Tweed
Woven for the field.
Flannel
Brushed for winter.
Suede
Leather, softened.
How to wear Chicago Ivy.
Our perception of the look. Take it, wear it, make it yours.
- Start with Ivy. A clean collar, an Oxford button down, a tailored trouser.
- Add the edge. Raw denim, heavy wool, or leather from military and workwear.
- Layer for the lake. Oxford, then knit or vest, then overcoat.
- Buy once. Hand it down. Small batch, mended, never fast fashion.
Fast fashion asks you to buy something new every season.Chicago Ivy asks you to buy once, and pass it on.
Small Batch · Serialized · Mended · HeirloomThe history behind the style.
- James R. Grossman, Land of Hope: Chicago, Black Southerners, and the Great Migration. University of Chicago Press, 1989.
- St. Clair Drake and Horace R. Cayton, Black Metropolis: A Study of Negro Life in a Northern City. 1945. Reissued by the University of Chicago Press, 1993 and 2015.
- "Great Migration," The Encyclopedia of Chicago. Newberry Library and Chicago Historical Society.
- "Clothing and Garment Manufacturing," The Encyclopedia of Chicago.
- "Hart, Schaffner & Marx," The Encyclopedia of Chicago.
- Joy L. Bivins and Rosemary K. Adams, Inspiring Beauty: 50 Years of Ebony Fashion Fair. Chicago History Museum.
- Chicago History Museum, The Great Migration.
- Nicholas Lemann, The Promised Land: The Great Black Migration and How It Changed America. 1991.
WearWolfe is not affiliated with these authors or institutions. Their work informed our story; any errors in how we tell it are ours.
Chicago Ivy, answered.
What is Chicago Ivy style?
Chicago Ivy is a menswear style defined by WearWolfe. It takes classic Ivy style and gives it an edge from vintage military, workwear, and jazz, rooted in the history of the Great Migration to Chicago's South Side.
Who created Chicago Ivy?
Chicago Ivy was defined by WearWolfe, a Chicago menswear brand founded by LeRyan Wolfe.
How is it different from traditional Ivy?
Traditional Ivy came from East Coast campuses. Chicago Ivy comes from the South Side. It keeps the Oxford and the tailored trouser, then adds raw selvage denim, heavy wool, and leather, worn with the style of Chicago jazz.
What fabrics are used?
Natural fabrics only: raw selvage denim, cotton Oxford cloth, corduroy, linen, wool, cashmere, merino, tweed, flannel, silk, leather, and suede.
Is Chicago Ivy fast fashion?
No. Every piece is made in a small batch and built to last for generations. Pieces are mended, not replaced. Our raw selvage denim comes with free repairs for life.
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