Holiday gift giving is all about unexpected surprises. In this spirit, we’ve come up with a shortlist of menswear staples that have stylish twists you won’t find on your man’s list this holiday season.

Investment bankers could use a lift in spirits with Prada’s crocodile leather Balmoral shoes, along with a ferociously textured croc-embossed wallet and money clip. If you’ve got the means, support the ailing retail industry by picking up BG’s super luxurious $20,000 Stefano Ricci briefcase—a piece that will lift any emotional disposition. But sometimes—especially in this economy—it’s the thought that counts, making Shanghai Watch a steal for €175 from Colette. For the entrepreneur with anti-corporate sartorial predilections, pick up a tattoo-printed tie from Tai Ties, Alexis Mabille‘s hand-embroidered bow-tie or Kilgour‘s colorful Murano glass cufflinks for some rebellious, yet stylish accents to those formal, power networking affairs.

If a guy on your gift list prides himself on being a fashion forerunner, then Band of Outsiders‘ slim interpretation of a pinpoint Oxford shirt is a good bet. Alternately, Robert Geller‘s jeans on Odin’s new e-commerce site are one of the best cuts on the market for quality and style, while Henrik Vibskov‘s Bauhaus scarf will chromatically punch up his wardrobe. For someone who has already achieved style maven status (and color is not enough), Martin Margiela‘s sci-fi sunglasses will make nothing short of an outré statement.

There’s plenty more for the passionate hobbyist too. Art collectors will enjoy a Richard Prince woman t-shirt by Marni, while outdoorsmen will cozy up to a Dries Van Noten long patch work cardigan, skiers will be perfectly bundled in Limoland‘s royal blue and yellow down coat (exclusive to oki-ni.com) and tennis players who want the buck conservative on court dress can rock Fred Perry‘s graphic polo shirt. Novice joggers and marathon runners alike can expect some fashionable mileage from Nike Sportswear‘s Techpack windrunner, but motorcyclists will need a leather jacket such as Rick Owens‘ signature lambskin number.

But, of course, first thing’s first: lay a foundation with Acne‘s narrow, tight fitting boxers.

—Robert Cordero