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If you’ve got a closet and two brain cells to rub together, you know that fall presents a unique annual opportunity, one that gets covered in-depth (and then some). Refreshing, restocking or replacing your used or unloved garment isn’t just a time-honored tradition, but a serious treat, especially if you don’t have to do any of the leg work in tracking down the styles — and, currently, the stack of serious savings.
That’s right: As a fall gift from yours truly, I’ve tracked down a variety of versatile shoe styles built for cooler, wetter weather and guaranteed to slot directly into your current footwear rotation. There are approach shoes from Italian outdoor labels, hardwearing icons from heritage brands like Red Wing and L.L.Bean, even some Maine-made leather boat shoes. Find it all below.
Diemme Cornaro Suede Hiking Sneaker
Are we in for another season of approach shoes? All the signs indicate yes. Get ahead of the curb — and 50% off traditional retail — with these sleek Diemme hikers at Mr Porter.
Red Wing 6″ Iron Ranger Lug Boot
Is there a more fall boot brand than Minnesota-based heritage brand Red Wing? (Answer: no.) Enjoy a rare sale of the label’s Iron Ranger boot while you can.
On Cloudmonster 3 Road Running Shoe
Pretty bold of On to mark down their top-on-the-line daily trainer by a whopping $70 during peak marathon season. But, then again, the brand’s been making some crazy moves as of late.
Yuketen Italian Hex Eye Boat Shoe
I’ll keep preaching the Maine-made word of Yuketen’s handmade leather footwear until every guy in New York City starts wearing them.
Ugg Tasman II Slipper
A fleece-lined, suede-upper slipper that you can wear well beyond the dog walk? For an extra $40 off? That’s a fall score if I’ve ever heard of one.
New Balance Fresh Foam X 880v15 Road Running Shoe
One of Harry Styles’s preferred daily trainers is now on sale.

