Officially, the Best Boots for Fall

Rain doesn’t stand a chance against these shoes.

View in a Browser Saturday, October 03, 2026   The Holy Grail of fall menswear is a boot that can do it all—like, actually do it all. This week, I went from a nor'easter in New York to two days of non-stop rain in Chicago. My preferred boots have no trouble with fancy hotel bars, these two cities' lousy airports, or rainy walks across town. Find them and nine others, below. —Luke Guillory, commerce editor   10 Waterproof Boots for Unexpected Nasty Weather Rain doesn’t stand a chance against these shoes. SHOP NOW   The 10 Best Watch Deals from October Prime Day The sale doesn’t kick off until October 6, but we’ve found some heat on deep discount. SHOP NOW   These Dickies Will Always Be My “Break Glass in Case of Emergency” Pants With all the fancy stuff I own, I still come back to a $40 pair of 874’s more often than not. SHOP NOW   The New Beats 360 Are the Most Interesting Headphones We’ve Tried in Years We thought they were AirPods Max for gym bros, but they’re so much more. SHOP NOW   The Best Transitional Weather Jackets for When It’s 50 Degrees in the Morning and 70 by Lunch And after fall, they turn into winter layering staples. SHOP NOW   21 Fun New Fragrances That Launched in September Fall is here, and with it comes a whole slew of new scents. SHOP NOW   Follow Us Unsubscribe | Manage Preferences | Privacy Notice | CA Notice at Collection Esquire is a publication of Hearst Magazines. ©2026 Hearst Magazine Media, Inc. All Rights Reserved. This email was sent by Hearst Magazines, 300 West 57th Street, New York, NY 10019-3779