Where are the best Cyber Monday deals on boots and shoes? (2021)

11/30 Update: Alright everybody, that’s a wrap for 2021. I’ll leave this page up for reference, but we will no longer be updating it. Hope you picked up something great!

It’s that time of the year again! Cyber Monday sales are starting up and offering a chance to save a little bit off that pair you’ve been looking for. Your author will be tracking the best deals on boots, sneakers, oxfords, and handsewns here. See one I missed or having a sale yourself? Shoot me an email at 100wears@gmail.com and I’ll get you added below.

By the way, a couple of the links below are affiliate. These help keep the lights on here, but don’t impact the price you pay. When compiling this list, best price always came first, even if that meant going with a store that 100wears doesn’t partner with.

Full List:

Cash Back Deals

Always be sure to check Rakuten for cash back before you buy. If you’ve never used them before, it’s just an extra certain percentage back from your purchase – it doesn’t prevent any other deals. Just make sure you’ve turned off any adblocker first or it won’t register.

If you’ve never signed up before, here is an affiliate link that will get you $30 [now $40!] back on your first purchase of $30 $40 or more within 90 days of signing up. I believe this will only work for those of you located within the U.S. and Canada.


The deals change constantly, sometimes multiple times a day. I would encourage you to use this list as a guide but to check before any purchase as it could have gone up or down.

  • Adidas: 15%
  • Allen Edmonds: 12%
  • Clarks: 15%
  • Finish Line: 12%
  • Helm Boots: 2.5%
  • New Balance: 3%
  • Nike: 12%
  • Todd Snyder: 1%

Adidas Cyber Monday:

Adidas - Wikipedia

In what will be an unfortunately common theme for Black Friday 2021, Adidas doesn’t have any good site-wide sales, instead focusing on individual models. Use code: CYBERDEAL. A few worth checking out are the Supernova+ for $84, Ultraboost 21 for $135, Boost Slides for $48, and Cork Slides for $56. Don’t forget to stack Rakuten cash back – for many of the Black Friday day shoes the discount from them is bigger than from Adidas!

Adidas’ eBay store actually beats their website on a few models. A few to check out include these Ice Cream Ultraboosts for $90, the new FutureNatural for $84, the Ultraboost 21 for $126, or the Stan Smith alternative Rod Laver for $63.

Alden Cyber Monday:

Alden Shoe Company Logo Vector (.SVG) Free Download

The Shoe Mart is offering $25 off every pair of Alden seconds with code CM2021. In other words, if you order one pair it’s $25 off, two pairs is $50 off, etc. As always with the Shoe Mart, you need an approved account to access the seconds (sign up and then email them and ask for access).

Deals include the classic brown chromexcel Indy for $375, and Color 8 shell LHS penny loafers for $495 [Update: Almost sold out!].


Allen Edmonds Cyber Monday:

Allen Edmonds is currently running 25% off almost everything, with shell shoes excluded. 25% off full priced models isn’t great for AEs (you can get 15% off every day with an email sign up), but stacking on the sale section can lead to some good finds. Sizing is pretty limited though.

Be sure to check for cash back on Rakuten!

Beckett Simonon Cyber Monday:


Beckett Simonon is currently running a deal for two pairs of dress shoes for $289. This is actually the only company on the list that actually costs less than last year’s pricing. Consider the inflation and supply chain issues that companies are facing, that is pretty impressive. For my money, the two pairs I would pick up would probably be the Yates Oxford in Bordeaux and the Dunham Derby in Medium Brown.

Cobbler Union Cyber Monday:

Cobbler Union is holding an “Up to 50% [now 60%!] off” Black Friday sale. Take the “up to” part seriously, because there is exactly 1 pair that is close to that. A lot of people are not aware of Cobbler Union, but they make some really great stuff, especially for the price.


Their shapes are definitely more elongated than most Americans are used to, so if you’re an American not into European styles I would suggest sticking with shoes that are traditionally that design. I’m a sucker for their museum calf, and you can find that material on their traditional “Richard” oxford in Oxblood for $295, or on their “Benjamin Jr” Chelsea in Brown for $325 [now 315].

Crockett & Jones Cyber Monday:

Handmade English Shoes, Made in England | Crockett & Jones – Crockett &  Jones UK

Todd Synder is running 25% off their website, and while their exclusion list includes most of their higher end footwear, their Crockett & Jones shoes are all included. Some great options are the Coniston boot for $544, or the absolute classic Hallam Cap Toe Oxford in Black for $476. Use code CYBER25.

Don’t forget to double up with cash back sites. Rakuten is offering 1% at time of writing, which isn’t a huge percentage but when you’re spending that much, every little bit helps!

Grant Stone Cyber Monday:

Grant Stone is offering 25% off any order of $400 or more, using code BlackFriday2021. B grades, final sale, and limited release included! This isn’t quite as good as their deal last year, but would you go back to 2020 to save $20 on some boots? Probably not. It is worth noting that none of their footwear available is over $400, so you’ll be looking at picking up at least a couple of pairs or some accessories.

Personal favorites of mine include their tassel loafer, which is pretty much the only one that comes in a last a normal person can fit into, and their Diesel in Burgundy Kudu.


Helm Boots Cyber Monday:

HELM Boots

Helm Boots is offering 30% off sitewide, along with free shipping and returns. This stacks with their sale, and puts some items in some pretty appealing price points – assuming you can find your size. The suede versions of the Hollis boots are down to just $167.30. The Bradley, their captoe derby, is $104.30.

Helm regularly has cash back on Rakuten, so be sure to check before you buy!

Jay Butler Cyber Monday:

Jay Butler

Jay Butler is offering 20% off sitewide, using code JBBF2021. The Cromwell Loafer (reviewed here) was one of the “pandemic all-stars” in my rotation. They are definitely worth checking out if you’re looking for some loafers. All the non-exotic shoes on their site are down to $156! That is a lot of value for the price.

Quoddy Cyber Monday:

Quoddy Resole & Refurbish Service – Quoddy.com

Domestic Domestic is offering 30% [now down to 20%] [now 20% under $200 with TEAMKEVIN and 30% off over $200 with TEAMBUDDY] off sitewide, including Quoddy. [NOTE: Their old deal of 40% off seems to still be working using code SWEETPOTATO, but it was supposed to expire several days ago] Great options include their Mule for $179 (a lot of people over on r/goodyearwelt ordered this at full price because they thought it was a limited run, so finding it on a deal is pretty great for those who waited). They also have the classic Blucher in Whiskey Cavalier and a Brick sole for $167. I actually own this pair, check out the review here.

Koio Cyber Monday:

Koio sneakers are running 20% off for Black Friday [now 30%!], no code needed. Their low top is pretty clearly designed to be a common projects alternative, but I was never a huge fan of the gold lettering on those anyway, so finding an alternative without it might not be a bad thing. Obviously, their main product is the Capri sneaker – priced at $214.40 [now 187] for this sale. Interesting colorways include the two tone Bianco, the striking Lavender, and the classic Triple White.


Meermin Cyber Monday:

Meermin Shoes

Meermin has opened up their Black Friday sale to the general public, and while I’m not as big on Meermin as some others, there are some undeniable deals here. A few that really blew me away were these Longwings for just $136, and these Chukkas for $157. Unfortunately, it looks like most of the sale is now only very limited sizes, but here is the full list if you want to check out what’s left.

Finally, if you’re really trying to make a statement, there are these Purple Suede Oxfords for $127. Please shoot me an email with pictures if you buy these!

New Balance Cyber Monday:

New Balance logo and symbol, meaning, history, PNG

New Balance is currently running running 25% off selected models on their website. Options are unfortunately a bit limited, but they do have the 574v2 for $60 dollars, and the 997H for $67.50.

Nick’s Boots Cyber Monday:

Nicks Boots

Nick’s has opened up their Black Friday deal with their typical 10% off. Pricing as-marked in search, but the product pages still show MSRP. As is typical, their sales are oddly limited – this time only on Predator Orange, Black CXL, Color 8 CXL, and in-stock boots. Why is custom order brown CXL off limits this time? The world may never know.

Even if they do have weird limitations, there are still some good gets here. It’s worth taking a look at the Color 8 Americana for $512, the Falcon in Predator Orange for $485, or (the one I would get for my money) the Urban Logger in Waxed Flesh with the Honey sole for $485.


Nike Cyber Monday:

Swoosh - Wikipedia

Nike is running their yearly Black Friday sale, with discounts on select styles, and an additional 20% off with code CYBER. There are actually a surprising number of good deals in there. A few standouts include the Hot Lime Air Max 90 for $91, the ZoomX Invincible (one of the most comfortable sneakers ever) for $136, and the Air Presto for $94.

If you’re looking for some serious running sneakers, they have the Zoom Tempo Next% for $152, The ZoomX Vaporfly Next% 2 for $190, and the Air Zoom Alphafly Next% for $208.

Oak Street Bootmakers Cyber Monday:

Oak Street Bootmakers

Oak Street Bootmakers is running a 20-30% off their entire line up for Black Friday, prices as marked. OSB makes almost every kind of shoe, so if you’re looking for it, they probably have it.

If boots are your thing, a few great options are the Trench Boot, in Rough Out here for $327, or the Field Boot in Carbon Bark Veg Tan and Raw Cord sole for $344.

If you’re looking for handsewns, they have one of the only handsewn tassel loafers available for $243, their Trail Oxford with a wedge sole for $229, or a Camp Moc (reviewed here) for $228. Seriously, we need to buy more of those tassel loafers to support them!

Finally, if you need something more formal, check out their wingtip for $347.

Rancourt Cyber Monday:

Rancourt is holding their once yearly sale, and this year the percent off is 15% [now 25%!] back down to 15% and only on non-sale items, using code HOLIDAY21, expires at 11:59 PM EST on 11/29. Applies to everything, so you can grab some nice blue ranger mocs for under $200 [SOLD OUT], or save almost $100 on a pair of shell loafers. Your author is a big fan of Rancourt, and currently has more Rancourts than any other stitched brand. If you’re looking for some reviews, check out the Read Boat Shoe, the Horsebit Loafer, or the Blake Wingtip.

Red Wing Cyber Monday:

Domestic Domestic is offering 40% off site wide, including on their First-quality Red Wings, using code SWEETPOTATO. My personal pick would probably be the 1907, with the double stitched welt, for just $186 (!), but it’s hard to complain about the classic Iron Ranger in Copper Rough and Tough for $210.

Red Wing removed from sale.

Reebok Cyber Monday:

Reebok logo and symbol, meaning, history, PNG

Bok boys looking to grab a pair of Adidas-made Reeboks before the sale can pick up (almost) anything for 35% off, with an extra 50% off sale, over on Reebok’s website. Some of the Questions actually do qualify, but others don’t and neither do the Pumps. If you’re looking for something more basic, the Club C is included in some colorways.

Be sure to check Rakuten for cash back, at time of writing they are offering an additional 10% back.

R.M. Williams Cyber Monday:

Amazon (of all places!) currently is running a sale on R.M. Williams for Black Friday, taking 20-30% off some of their best known models. That means the Comfort Craftsman for $396, the Classic Craftsman for $396, or the Turnout for just $346!

I picked up a pair from this one myself.

T.B. Phelps Cyber Monday:

T.B. Phelps

TB Phelps is running a tiered percentage off on their website for Black Friday, discount applied at check out. $50-$100 is 10%, $100-$250 is 15%, and $250+ is 20%. If you’ve never heard of TB Phelps before, they offer some really interesting leathers that can be hard to find elsewhere. The 100wears review of their Weekender Elkskin Chukka can be found here, and that boot is currently on sale for $208.

You can also find their Deerskin penny loafer for $224, and their sheepskin penny loafer for $204 by itself, or $192 if you find $10 in other stuff to add to your cart.

Tricker’s Cyber Monday:

Tricker's Blair Mens Penny Loafer Shoe in Black Leather | Tricker's

Tricker’s Outlet is running a 20% off sale, added automatically when in cart. Sizing is fairly limited, but there are some real deals if you can find something that works. I’ve converted the prices to USD here, but the website and the transaction is in GBP so the actual price you pay may go up or down depending on the currency changes.

A few great options are these chunky crepe-soled Longwings for $187, or Chukka for $262. Of course, there is also the classic Bourton Country Shoe for $245, and the Stow for $262.

Note: Tricker’s is located in the U.K., and while shipping to the U.S. and Canada is free they will not cover returns. Sending a shoe back to the U.K. can be quite a bit, so I’d suggest that you be sure of your size before ordering.

Truman Boots Cyber Monday:

Blue Owl is having 20% off site wide, including their Trumans, code is FEAST20. Sizing is extremely limited, though I would have been tempted by either of the boots on their site if they had mine. I think the star is the Veldt Boot for $388, even with my past history with Truman that is hard to turn down. The Ranger Boot also looks great, but comes in at a much dearer $476 after discount [update: just a size 9.5 left].

Truman themselves are also having a holiday sale. Prices as marked. A lot of these are seconds quality, so be sure to completely read the product description before buying. I’m extremely hesitant to recommend seconds, but it might be worth picking up the pairs that are not. One that caught my eye was the Navy Hot Shot for $345.

UNMAKRED Cyber Monday:

Unmarked Handmade Mexican Señor Boots

Unmarked is having 20% [now 30%] off sitewide, including sale. While I’ve never had a chance to try a pair, they definitely have some interesting designs that could be worth checking out. I’m getting real Yuketen vibes from their Jack Penny Loafer ($232), and the Ebony Black Toro Mini Welt Chelsea is really appealing at just $139.

Viberg Cyber Monday:

Viberg Boot - Since 1931 – VIBERG North America

Blue Button Shop has Vibergs on sale for 25% off using code BF25, prices on their website are in CAD, and while they have free shipping to the great white north, shipping to the U.S. is $15. There are some really good deals to be had here. A few good ones are this Burned Oak Dublin Service Boot for $515 USD, or this Olive Scout for $571 USD. Unfortunate news for the big feet boys, they only go up to size 11.

Standard and Strange is doing an extra 20% off sale items with code GIMME20. There are some great Viberg options, though sizing is pretty limited. The Service Boot in Dublin English is just $520 [SOLD OUT], and they have the Service Boot in Mocha [SOLD OUT], Brown CXL [SOLD OUT], and the Chelsea in Snuff Suede [SOLD OUT], all for $440! Just be aware – these items are all final sale. You can buy insurance for returns, but it costs about 10% of the total price of the boot.

Miloh Shop is offering 20% off sitewide, including Vibergs with some really great make ups, using code BF2021. The listed prices are in Canadian, which currently converts at about .78 cents to the US dollar. These Washed Horsehide Service Boots are my favorite and are just $614 USD [SOLD OUT]. But you can also find the classic CXL Service Boot for just $577! If you happen to find your size they also have a Grey Miniripple and a Oiled Calf for under $500 USD.

White’s Boots Cyber Monday:

White’s themselves are having an “up to” 25% 30% off sale. They’ve added the non-speedhooked version of the MP as a closeout for 30% off! Both the Dainite MP and Half Lug MP options are $433.96 – though only in-stock pairs. Less popular but an even more affordable pair is the Foreman Roughout, which is just $309.36. The Foreman is built on the 610 last, which is a lower arch, but for the price of a pair of Red Wings these are an absolute steal.

Their traditional goodyear welted boots are 25% off. This means the Main Street is between $288 and $324 depending on your leather and sole choice. The Otto Derby and Kinney Chuckka are both $288.

White’s eBay store also just restocked, and they can have some amazing deals – assuming they have a pair in your size. These will also generally ship lightning quick, so you won’t have to wait 5 months to get your pair. My favorite might be these chunky 350’s with a full lugged sole for $349. Just be aware, the Main Streets on ebay are actually more than one ones on their main store.

Baker’s is having an early Black Friday sale on White’s boots with a full 20%! (prices as marked). This is about as good as it gets for White’s. Great options include the MP (I got my MPs from Bakers’s during their last Black Friday sale – Review Here) which starts at $472, or the Baker’s exclusive Bounty Hunter starting at $480.