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A version of this article originally appeared on Glamour US.

Price: US$22,700 Patek Philippe Calatrava 6119G No dress watch list would be complete without a Patek Philippe Calatrava, the best current example of which has to be the 6119 Clous de Paris variant, as featured in an edition of our Versus column

Features at a Glance Advertisement - Continue Reading Below Pros Fully waterproof and scuff-resistant Lug sole grips the ground and keeps every step stable Pairs well with relaxed denim, cargos, and winter fits Will never go out of style Made with 400 grams of PrimaLoft for warmth Cons Breaks in after a couple days Timberlands classic work boot has outlasted trendy styles for decades because its durable, has a timeless design, and goes with everything

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