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A dress shirt with a tie and jeans is a timeless look that is versatile, stylish, and appropriate for a variety of events

The Rows Canal loafer is, like everything from the brand, admittedly pricey, but the collapsible back and soft leather construction means putting it on is a cinch, which helps with the cost-per-wear calculations

Book a Fancy Evening and Go All Out While a fancy evening can be stuffy, you can have a wonderful time wining and dining at a Michelin-star restaurant or another upscale restaurant that youve been dying to go to