Now Is the Perfect Time to Buy a Pair of Normal Shoes, Actually

From Red Wing to New Balance, eight pairs of on-sale footwear styles to add to your seasonal rotation

October 1, 2026 3:25 pm EDT
Pair of gray suede loafers with tan interiors on a red, black, and white patterned rug
Fall is an ideal time to restock your footwear. A ton is currently on sale
Huckberry

The Gist

This fall, savvy shoppers can snag serious savings on a curated selection of versatile, durable shoes perfect for cooler, wetter weather, from heritage boots to sleek hiking sneakers.

Key Takeaways

  • The guide highlights a variety of shoe styles, including approach shoes, penny loafers, lug boots, running shoes, boat shoes and slippers.
  • Featured footwear comes from well-known brands such as Diemme, Rhodes Footwear, Red Wing, On, Yuketen, Ugg, L.L.Bean and New Balance.
  • Many recommended shoes are currently available at significant discounts, with some more than 50% off their traditional retail price.

Nota bene: All products in this article are independently selected and vetted by InsideHook editors. If you buy something, we may earn an affiliate commission.

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
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.

Rhodes Footwear Mini Lug Penny Loafer
Rhodes Footwear Mini Lug Penny Loafer

Business up top, party below. Savings all over.

Red Wing 6″ Iron Ranger Lug Boot
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
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
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
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.

L.L.Bean 8″ Bean Boot
L.L.Bean 8″ Bean Boot

Bean’s iconic duck boot is an all-time classic for a reason.

Paolo Sandoval

Paolo Sandoval

Paolo Sandoval is Style Editor at InsideHook, having previously contributed to Valet Mag. An expert when it comes to vintage denim, soccer kits and tailoring, Paolo reports on style, grooming, wellness, menswear trends, celebrity, media and other pursuits tangential to looking and feeling like a million bucks, and is the voice behind the InsideHook fashion newsletter, The Stitch. You can reach him at psandoval@insidehook.com.
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