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Sweater: J. Crew Factory - $41 Shirt: Hawkings McGill - Urban Outfitters - $20 (similar) Jeans: American Eagle - $39 Boots: Dune - Topman - ...

The Vintage Watch: Build The Ultimate Watch Collection

Give your ensembles a rugged twist with these Zara jeans that play on fall's trend of rustic living. Pair them with other off-duty items, such as a light-colored denim shirt or a chunky cable-knit sweater. For bonus points, roll up the bottom cuff of these jeans and pair them with beat-up boots.

Casual Fridays can be tricky. "If you don't dress properly, your credibility will be undermined, even on casual days," says Ron Herzog, CEO of Fortune Personnel Consultants, an executive search firm in New York City.