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Having tried numerous pairs of inexpensive bots, we've assembled this list of the Best Dress Boots Under $100: Cuban Heel: Giorgio Brutini Calloway. Chukka Boot: Timberland Earthkeepers Brook Park. Chukka Boot: Nunn Bush Savage Plain Toe. Chelsea Boot: Giorgio Brutini Aaron. Monkstrap Boot: Stacy Adams Kason.

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Thomas Crick ladd formal chelsea boots in wood. £34.99. The North Face Back-To-Berkeley IV waterproof leather hiking boots in black. £155.00. -45%. MORE COLOURS. ASOS DESIGN lace up boots in grey suede. £50.00£27.50. Thomas Crick addison formal leather chelsea boots in black.

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Brown Timberlands are classic (and Drake-approved), but if your style leans more selvedge-and-flannel than Wu Tang hoodie, then Red Wing's Classic Moc should be the work boot of choice. Danner.

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