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Top 5 Shoes for Fall

This post was originally published on October 13, 2013 and was updated on September 23, 2020.

In Nicholas Antongiovanni’s The Suit, he makes an astute observation we’d like to paraphrase: if your suits are akin to your home, then your shoes are akin to your car. The right pair of shoes will send the right message and make you feel (and perform) your best even if you’re working from home because of Covid.

We don’t mean to discourage you from binging on a shoe collection, but you don’t need an entire stable of shoes. Just a few pairs to rotate through. Below, we offer our top five shoes for fall 2020 that every man should own.

Chelsea Boots

chelsea boot with lug sole
Chelsea boot with a casual lug sole.

Popularized by the Beatles in their early days, a Chelsea boot refers to a laceless, ankle-height boot. They’re great as the temperature drops and can pair just as easily with a suit as they do with custom jeans.


black wingtip mens laceupsThough we see them with suits quite often, wingtips are actually a slightly more casual footwear option relative to, say, a cap-toe. You can certainly throw them on with a suit, but they truly shine on more casual fall pants – denim, tailored corduroy trousers, and the like.


mens fashion sneakerYou’re going to need something to go with your custom casual wear. A slim, streamlined sneaker will do just the trick, finishing your casual look without too much polish.

Whatever you do, don’t go for the nearest available athletic shoe. Even if you’re a dad, you don’t need to dress like one.

Penny Loafers

brown suede penny loafer for menThough we wrote about loafers as a great summer shoe, they work extremely well in fall in darker colors and textured materials. Versatile and handsome, pick up a slim pair for your dressy outfits and a chunkier pair for your more casual ones.


brown derby mens shoesAlso known as “derbies,” bluchers are the more casual of dressy lace-ups (the more formal being an oxford/balmoral). Though we often see them on traditionally dressy ensembles like suits, they’re a better match for today’s professional uniform: a sport coat and jeans.

Conclusion / Where To Buy

We don’t yet have a custom shoe program here at the shop. Our suggestion? Head over to Blue Sole Shoes at 18th & Chestnut. Check out their Instagram page for inspiration, and let them know we sent you.

Ready to flesh out your fall wardrobe? Give us a call at 215-310-0219 or email us at info@henrydavidsen.com to schedule a consultation.

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