Introduction This paper seeks to compare Urban Outfitters, Inc, (URBN) with Tiffany & Co. (TIF) under the retail business industry using their annual reports and other appropriate source materials. In making the evaluation and comparison of the two companies. This paper will analyze their business environment, their strategies and their financial position and performance URBN as a lifestyle specialty retail company, operates specialty retail stores under the Urban Outfitters, Anthropologie, Free People, and Terrain brands. Its Urban Outfitters stores offer women’s and men’s fashion apparel, gifts, footwear and accessories. URBN stores also deal on mix of shower curtains, books, apartment wares, such as rugs, pillows, candles and novelties for young adults. One the other hand, its Anthropologie stores make available to customers women’ casual apparel and accessories, and a range of gifts and decorative items. They also offer rugs, lightning products, beddings, and gifts for women as part of home furnishings. URBN’s Free People retail stores on another part, primarily make available Free People branded merchandise, as could be found in casual women’s apparel, gifts targeted to young contemporary women, accessories. Terrain retail stores as separated do offer lifestyle home and garden products combined with antiques, live plants and flowers. Parts of the latter products are the different landscape and design service solutions for men and women. As URBN designs, develops, and market private apparel lines of young women’s casual wear, in tops, bottoms, sweaters, and dresses, one could prove its wide coverage in approximately 1,800 department and specialty stores. This is further expanded by offering its products directly to consumer via online using various websites as urbaboutfitters.com, anthropologies.com, and urbanoutfitters.co.uk. With more than 140 Urban Outfitter stores, 121 Anthropologies stores and 30 Free People Stores, the company is evidently big and continues to grow big. 1 On other hand, Tiffany & Co, which is based in New York, New York, has its many subsidiaries and through them, the company is engaged in the design, manufacture, and detail of fine jewelry. The company is still considered as part of the retail business and instead of dealing with apparels as that of URBN, TIF has its jewelry products. From this wide array of jewelries come the gemstone jewelry and gemstone and band rings, diamond rings and wedding bands for brides and grooms, and non-gemstone, gold, or platinum jewelry, as well as sterling silver jewelry. TIF is also known for its offer of TIFFANY & CO. brand merchandise that may be noticed in timepieces and clocks and sterling silver merchandise, such as those in trophies, key holders, flatware, hollowware, desks accessories, picture frames and even writing instruments, fashion accessories and eyewear products. Thus, it marketing strategies become evident with its customers through retail sales, business-to-business direct selling operations, and catalogues. It also actively engaged in wholesale distribution in the US and internationally. TIF has also its products sold through TIFFANY & CO stores in many part of US and department stores boutiques in Japan. It expansion