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For when you need a structured, boardroom-appropriate bag, black leather will always get the job done. The Break It Out Tote by Kenneth Cole New York has a tall, rectangular silhouette and two versatile carrying options. Its exterior is finished with large pockets for maximum organization and rugged – yet somehow sleek – nickel hardware.

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Flint & Tinder has always been one of our favorites because they make updated, high-quality American staples–without being fussy, over-designed or bearing a huge price tag. Our latest favorite? This Flannel-Lined Waxed Trucker Jacket. With classical trucker jacket styling and a flannel-lining for warmth, this Made in the USA trucker jacket is best in class. In addition to Martexin 7oz sailcloth exterior in eight different color options, you get fully-lined body / sleeves, interior media pocket, button-flap chest pocket, 2 welt hand pockets, and finishing like F & T antique metal buttons and a modern fit. Get yours today at Huckberry