5. Worn-in jeans
We can hear you, Tommy! This soft, relaxed, slim-fit, worn-in-to-perfection pair from Hilfiger Edition is your ticket to comfort on chilly walks, beer runs, or all-day fall foliage excursions. Dress them up, down, or anywhere in-between—they’re a new classic.
Jeans: Hilfiger Edition ($230, tommy.com)
Jacket: Polo Ralph Lauren ($995, ralphlauren.com)
Shirt: Dockers ($68, dockers.com)
Henley: Joe’s ($138, joesjeans.com)
Shoes: Ugg, ($150, ugg.com)
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