This paper will address the demise of two of the early twentieth century's most successful fashion enterprises, the couture houses of Lady Duff Gordon—whose business was known as Lucile Ltd.—and Paul Poiret. The paper will establish a chronology of events and describe the financial factors that led to their dissolution. Duff Gordon and Poiret were creative, innovative designers as well as masterful self-promoters who came to preside over "lifestyle" companies. Despite their success, both Duff Gordon and Poiret severed ties with their couture houses in the 1920s. During the 1930s the businesses closed for good, but the economic depression was only partly responsible. How and why, then, did it all go wrong? What lessons can be drawn from their early experience with incorporation, limited partnerships, product licensing, and the launching of subsidiary companies? With his extravagant displays aboard three river barges, one a functioning restaurant, at the 1925 Paris Exposition des Arts Décoratifs, Poiret may have demonstrated the folly of over-spending on publicity and promotion. In the case of Lucile Ltd., Lady Duff Gordon's partnership with a ready-to-wear manufacturer may have signaled the beginning of the end, as the various branches of her international company split apart. Their failures were business failures, not creative ones, and the strategic marginalization of these designers by their business partners only proved to be bad for business.