Where to Match Your Hotel to Your Outfit

Newcomer Armani Hotel debuted last year, adding to the hipness quotient of Milano hospitality. Armani Hotel makes its home in a more urban location along via Manzoni, under a modern rooftop atrium that puts a fashionable hat on the building's historic masonry facade. Inside, Armani uses muted colors and signature furnishings, many available for purchase through his Armani Casa line. An Armani-branded eatery features a bold design statement of black-and-white marble floors under windows illuminated by the Milanese skyline. The first Armani Hotel is in Dubai; Armani Hotels & Resorts is actually a partnership between Armani and Dubai-based Emaar, which also developed the Burj Khalifa and Dubai Mall.

Those who prefer a little less corporate supervision can book into the Hotel Moschino Milan, which was born out of the Italian fashion house Moschino and the work of its lead designer, Rossella Jardini. Occupying a former 19th century rail station, the neoclassical structure feels as though it fell down one glamorous rabbit hole for its four floors and 65 guest rooms -- some of the most whimsically designed spaces you'll experience. Inspired by fairy tales and dreams, the hotel (managed by Italy's Hotelphilosophy Collection) has rooms mixing the occasional hanging poodle lamp with dress-shaped headboards and poster beds made of tree trunks. It is also home to an ever-changing eatery led by Michelin-star chef Moreno Cedroni and ART Spa that mixes modern art into an ethereal theme.

Away from Milan, the Ferragamo family opts not to put its name on the collection known as Lugarno Hotels, which operates such style-centric properties as the Continental in Florence and Portrait Suites in Rome. In addition to operating hotels, the Ferragamo Group manages a series of high-end apartments that offer voguish abodes for those looking for something bigger than just a hotel room. Less known, however, is the group's recent sea explorations, including the Scarlino Yacht Club and Residences, which brings the Ferragamo lifestyle to a permanent residential community and marina, as well as its Swan Sailing Yacht available for Aeolian and Balearic charters with breathtaking interiors by Florentine architect Michele Bonan.