Chicago Classic Fit Pleated 2-Piece Suit
A roomier Chicago Fit suit that keeps traditional pleated trousers in the Hart Schaffner Marx rotation.
Prices are a snapshot from when this page was built — confirm on the retailer's site.
Story & heritage
The pleated Chicago suit reflects the brand’s long-running fit logic: Hart Schaffner Marx’s Chicago Fit is described by the label as a traditional, easy-fitting cut designed around comfort and longevity rather than a narrow silhouette.
For a house known for American tailored clothing, the pleated trouser keeps the suit close to classic office and occasion dressing while sitting beside the flat-front version in current retail assortments.
Materials & craft
Dillard’s product details describe the Chicago Fit pleated suit with a two-button jacket, center vent, notch lapel and three inside utility pockets. The trousers are cut generously through the seat and thigh with single pleats, knee lining and a zip fly with button closure.
The listed fabric is a wool/Lycra blend, a practical tailoring cloth that pairs worsted-suit polish with a little recovery for daily wear.
How to choose & style
Treat it as the classic boardroom HSM: white or blue shirt, silk tie and black or dark-brown dress shoes. The pleated trouser looks most balanced with a proper break rather than an aggressively cropped hem.
Navy softens the traditional silhouette; black makes it sharper for evening or formal office settings.
