Shopping Guides

Cyber Monday 2024: The Best Shoe and Boot Deals for 2024

Well, here we are again. The best time of the year for deals, Black Friday. We may not quite be at the actual Black Friday yet, but the deals have already started. If you’re a guy shopping for a new pair (or someone shopping for someone else) these deals might help you save a buck or two.

Just for awareness, some of the links below are affiliate links. They don’t cost you anything extra, but there is a commission if you buy through them. You should know, I always pick the best deals available with no preference given for affiliate links over regular ones.

See a deal I missed? Shoot me an email over at 100wears@gmail.com.

Last Updated: 12/2


Allen Edmonds Cyber Monday 2024

Allen Edmonds has started their Black Friday sale. Options are extremely limited at the moment, though if previous years are any indication they will probably expand availability before Cyber Monday. Of course, if they sell out of what you want, that doesn’t do you any good.

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The deal this year is definitely the Fifth Avenue, which costs $199 in a variety of colors. At time of posting nearly every size is available in nearly every color.


Carmina Cyber Monday 2024

Carmina has started up their yearly Black Friday sale, with 25% off around 25 different pairs.

A pair I would have picked up for myself if they had my size were the unlined penny loafers for just $296. Of course, I know that this time of year sees boots as far more popular. In this case, you might want to look at this pair of Work Boots for $394. A full size run is available at time of posting.


Caswell Boot Co. Cyber Monday 2024

The Washington D.C.-based Caswell Boot Co started offering a 15% off all ready to wear boots, price as marked. These include overstock, samples, and seconds, though if you’re going that way it’s best to read the description to know what you’re getting.

Due to the nature of their sale, most pairs only have one size available. If you’re interested in a pair of Caswells, your best bet is to poke around and see what they might have in your size.

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Cobbler Union Cyber Monday 2024

For Black Friday 2024, Cobber Union is offering “up to” 50% off on almost everything. There are two big qualifiers in that advertisement, but there are still some deals to be had. Prices as marked.

Availability will depend on sizing (my size only has 3 options to pick from) but it’s worth digging through if you’re looking for something more formal. My pick would probably be the Richard for $349.


Duckfeet Cyber Monday 2024

Duckfeet, the Dainish brand with the unique shape, is offering 20% off site wide. Discount applied at check out. When I reviewed a pair earlier this year I was really excited about them. That review ended up being one of the most popular posts of the year. If you were one of those readers who was on the fence about picking one up, nows your chance to get a pair at the biggest discount of the year.

Of course, I’d recommend the Faborg, priced at $230. It’s the classic boot by the brand, and the one I wear myself. If you want something a bit warmer, they offer the same boot with a wool lining for $25 more.


Frank’s Boots Cyber Monday 2024

Frank’s boots is offering a number of different deals for Black Friday.

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All MTO boots are discounted $100 (price as marked). All in stock boots are $100 off, code: BLACKFRIDAYSTOCK. Seconds are $25 off, code: BLACKFRIDAYSECONDS. Gift Cards are buy one get one, code: BLACKFRIDAYBOBO.

As of time of writing, gift cards can be used on sale items, though I imagine this is a bug and will be fixed at some point.

Frank’s customization options are already much more limited than White’s, so I’d suggest looking at the in-stock options if you want a pair. The T-2 Highlander for $475 is a lot of boot for the money.


Grant Stone Cyber Monday 2024

Grant Stone is back this year with another Black Friday deal, 20% off all carts over $400, automatically applied.

Of course, the best place to start is their sale section, as the discount does stack. It also works with their B-Grades. Availability will depend on your specific sizing, but I’d take a look there first, just in case.

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In addition, the brand new Baroda Boot is included.

Otherwise, I’d suggest taking a look at their loafers. I’ve said it countless times, their tassel loafer (278 in Suede) is my favorite piece of footwear that I own, and their bit loafer ($278 in Suede) looks amazing as well. The deal also applies to their limited editions.


Helm Boots Cyber Monday 2024

Helm Boots has started their full Black Friday sale with 35% off site wide. Discount automatically applied.

The first boot I’d recommend is the Zind, probably their best known boot and the Teak leather patinas really well. With the sale, you’re going to bring these down to just $191, a great price. The Hollis, which has a more durable and chunky sole, comes out at the same price.


Joseph Cheaney Cyber Monday 2024

If you just want a simple, well made pair of shoes, it’s hard to argue against Joseph Cheaney. Where as every other British brand has either gone out of business or hiked their prices sky high, Cheaney is still doing their thing, priced below Aldens.

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If you’re looking to pick up a pair, Brooklyn Tailors is offering 15% off all of their Cheaney models, using code EARLYBIRD15. I’d suggest taking a look at their Lime Oxford shoes, which work out to $344.


John Lofgren Cyber Monday 2024

The Japanese brand John Lofgren tends to come down hard on companies who list their product on sale, so any of these deals could be pulled before Black Friday. If you see something you like, it’s probably worth biting.

Blue Owl is offering 20% off on much of their site, including John Lofgren using code GRAVY. Selection is a bit spotty, but every model has at least a few sizes available. My favorite (and one I might buy) is the M-43, priced at $746. Of course, I have to mention their engineers, which even discounted come to a pretty eye watering $956.


Meermin Cyber Monday 2024

Meermin is offering “up to” 50% off on select items for Black Friday. The 50% off is pretty rare, but there is 30% off a bunch different options. Prices as marked.

There is a small number of shell cordovan options, but sizing is pretty limited.

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One you should probably consider is this extremely handsome PCT boot in saddle calf for $192. The big sizes are sold out, but otherwise there is a full size run. If you want something a bit more formal, their Chelsea is actually cheaper than during their seconds sale at $180.


Parkhurst Cyber Monday 2024

Parkhurst is offering what I believe is their very first sale with no restrictions. You can get 15% off sitewide using code CORNY.

I’d suggest starting with the samples and seconds section. The code stacks with the already discounted pricing, offering some great prices on Parkhurst. Options are limited, but I’d check out the Richmond in Mocha for $295 if you’re a size 7.5 or 9.5.

This is the first time I can remember being able to get something in their Spruce Kudu on sale, and what I would get from their full price options. The Niagara has a lot of sizes available at time of writing, and comes out to $355.


Oak Street Bootmakers Cyber Monday 2024

Oak Street Bootmakers has started their biggest sale of the year, with discounts ranging from 20-40% off.

As always, I have to start off by reccomending my favorite pair of shoes Oak Street Bootmakers makes – the Camp Moc in CXL Roughout. This year the price comes to $208.

After that, I’d suggest taking a look at their Limited Edition boots. You can find pairs in Kudu, Mohawk, Dublin, Horse, and more there all for 20% off.

If you want something a bit more standard, their excellent Field Boot has a full size run available, and is a full 40% off. It works out to $310, about as affordable as you’ll be able to find hand-lasted American-made boots.


Red Wing Cyber Monday 2024

Iron Shop Provisions is first out of the gate with some Red Wing deals this Black Friday, with discounts on several different pairs. Be aware, Iron Shop plans on offering different deals as the week goes on so prices may go up or down depending on when you click through.

Sizes are a bit limited, but if you happen to fit, I’m a big fan of the 1907 Moc Toe for $299.

Next to offer deals is Stag Provisions, with 20% off site wide. Stag offers some really cool make ups that are really hard to find anywhere else. I’d suggest starting with the Oro Russet Portage Japan Exclusive for $288. They Also have a few sizes in the Flatbox Beckman for $320.

If you’re feeling adventurous, Berkley Supply restocked their Red Wing Seconds. They have some really cool pairs – including Flatbox Beckmans for $300 and and the All-black Moc Toe for $162. No doubt these prices are about the best you’ll see on Red Wings but buyer beware. You might get a nearly perfect pair, or you might get one with major flaws.


R.M. Williams Cyber Monday 2024

In what is always one of the big surprises of the year for me, Amazon once again has the best deals on R.M. Williams boots this year. You can find the standard Craftsman for $404 or Comfort for $404. Some size have individual listings, so you can find the full list here.

Personally, I find the Turnout a bit more comfortable than the Craftsman and that can be found for the same $404.


Thursday Boots Cyber Monday 2024

Thursday doesn’t typically do sales, but there are two ways to get a discount this Black Friday. First, all orders qualify for a gift. What is the gift? I have no idea! But you’ll get something.

In addition to the gift, Thursday updated their Warehouse. Or, in other words, their overstock section. These are mostly odds and ends, but they do have the American-made Vanguard in Natty Waxed Roughout for just $179. Still available in a full size run at time of posting. That is a steal on an American made boot with Horween Chromexcel leather.


Trickers Cyber Monday 2024

While Trickers themselves are British, there are still opportunities to pick up a pair on this very American holiday.

The first place to look is A Fine Pair of Shoes, who are offering some pretty significant discounts on their Trickers models. Options are a bit limited, but prices are great at more than 50% off. They have both the Bourton Wingtip and the Bernwood PTB on sale.


Truman Boots Cyber Monday 2024

Truman is offering 2 deals for Black Friday. For most of us, you can find 20% off site wide using code BLACKFRIDAY24.

While my experience with Truman was less than stellar, if you want a low price, it does apply to their seconds. Availability depends on your exact size, but expect to pay around $300-350 for a pair depending on what type of leather you pick. There are not a ton of options, but there are some cool picks like these Black Cherry Bison options for $330.

Of course, you can also go with any of their full price models. Their selection is much smaller than previous years, but maybe that means they are no longer overextending themselves. Expect to pay around $400 for most models.


Unmarked Cyber Monday 2024

The Mexican brand Unmarked is offering 20% off site wide (Code: BLACK20), and 40% off last call pieces (Code: LAST40).

Of course, the first place to start is the last call section, which is already on sale with an additional 40% off applied at check out. Sizing is limited, especially as they just cleared inventory a few months ago when they moved factories, but it’s worth a poke around.

Sizing is a bit limited, even on their full priced line. However, one that still has a full size run is the very cool Toro Chelsea for $280. Made with a mix of goodyear welting and wooden nail construction, it offers really unique construction with a good look.


Viberg Cyber Monday 2024

Finding a pair of Vibergs on sale in 2024 is not an easy feat, but if you are looking for a pair, Franklin and Poe have your back. They are offering 20% off all Vibergs, using code BFCM24.

My personal favorite (and one I’d probably order if they carried my size) is the N1 Boot in rough out, priced at $688. If you want something more refined, they have three calf models. I think the Congnac looks best for $720, but the Vocalou in Annonay is great too for $688.

If you want something a bit more standard, Cultizm has 30% off site wide using code BW30. Right now they only have the 2030 Service Boot in Color 8, Black, and Brown. Though, it’s hard to argue with that you probably should pick up one of these if you’re only going to have one pair. They are priced in Euros at EUR664 each.

Of course, sometimes simple good ol’ currency arbitrage is best. Lost & Found have a number of Viberg models that don’t qualify for their sale, but are 20-30% off the U.S. MSRP. You can find the Natty CXL for $798, the Color 8 for $725, and a really cool tumbled horsehide for $692.


Wesco Cyber Monday 2024

Much like Viberg above, the very hard-to-find-on-sale Wescos are available for 20% off at Franklin and Poe. Use code BFCM24. Even better, you won’t need to wait 18 months to get your pair!

The pick of the litter for me is the Collaboration they did on the Jump boots, which are just $556. If you want something a bit more subtle, their Johannes is $10 less, and a bit more wearable in every day life.


White’s Boots Cyber Monday 2024

Baker’s is offering 20% off all custom White’s, prices as marked. If I was going to make one recommendation, it would be the Bounty Hunter. I love my pair in Latigo, $639, or you can get the standard leathers for $575.

If you want something a bit more svelte, the MP comes in at an identical $575.

If you’d rather not go the custom route, White’s themselves are offering “up to” 30% off site wide. Price as marked. Most boots are 20% off. While White’s own website used to be cheaper than Bakers, now they are the same price. The benefit is that, since there are no customizations, you can get them quicker.


Yanko Cyber Monday 2024

Yanko is a brand that probably doesn’t get the respect it deserves – but if you’d like to try them anyway, Skolyx has some for really good prices. Their filters don’t work particularly well, so you need to dig through a few different brands.

If they have your size, I’d definitely recommend taking a look at the Austerity brogue for just $143.


Birkenstock Cyber Monday 2024

While I don’t review them here on this site, I always have at least one pair of Birks by the door. If you’re looking to pick up a pair too, Stag Provisions has 20% off on all of the main line models. Price reflected in cart.

If you want to pick up the very popular Boston, you can a soft footbed for $128 in Taupe or Brown. If you want the shoe that the brand has been trying to push as the next big thing, the London is $2 more.

Of course, if you want to go classic, the Arizona is $112.


New Balance Cyber Monday 2024

Kicking off the New Balance deals, Lapstone and Hammer are offering 30% off their entire New Balance line. No code, price will show in cart.

At time of writing, there are a lot of choices, including the MiUSA models. The best deals are going to be the ones on sale – with this Teal 990v4 coming in at just over $100. Personally I suggest the freaking awesome 991v2, my current favorite sneaker.

They have this very holiday appropriately named Pinecone colorway on sale for $175.


Camel City Mill Cyber Monday 2024

Camel City Mill has started their Black Friday deal with discounts depending on how many pairs you buy. They need to be a single type bundled, so this is best if you’ve already found a pair that works well for your feet.

Discounts are 20% if you buy 3, 30% if you buy 5, or 40% if you buy 10. I’m not sure who needs 10 pairs of burly work socks designed to last 10+ years – but hey. It’s an option

It looks like they’ve mixed things up since I got my pairs, but I’d still recommend the boot wool work sock.


Darn Tough Cyber Monday 2024

GoBros.com is offering 25% off all Darn Tough socks, prices as marked. This is typically about as good as it gets for a site-wide sale.

As of time of writing, there is a ton of stock available in just about every size.

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