Shopping Guides

Best Shoe and Boot Deals: Labor Day 2023

Alright, you all know the drill. This is the article where you can find the best deals on men’s footwear. I’ll be updating this list as the weekend goes on, so if you don’t find the right option for you, be sure to check back!

Did I miss a sale you know about? Is your brand doing something and want to get it included here? Shoot me a note over at!

Frank’s Boots

While I’ve never had a pair in hand myself, Franks Boots is definitely starting to make a name for itself over on r/goodyearwelt. For labor day, they are offering $100 off almost any pair of boots (around 15-25% off, depending on the model). Collaborations, seconds, and a few others are excluded.

Without experience myself I hesitate to suggest anything in particular, but if you’ve been looking for a pair of Franks, definitely go check them out.

Grant Stone

The brand that always gets the most clicks on these sales threads – Grant Stone – is back at it for Labor Day 2023. This time they are offering an additional 20% off all sale shoes and boots using code LABORDAY20. As a big fan of their natural Minerva I’d definite suggest checking out the Ottawa or Edward for $237. However, if you want something a bit more chunky, the Brass in the always cool Color 8 is available for $237 as well.


It’s always a bit of a gamble on if they have your size, but B grades are also included.

Helm Boots

The brand from Austin is running a different tiered discount for Labor Day 2023. $150-249 is 15% off, and 250+ is 20% off.

The first thing to check out in my mind is the Zind in Teak for $236. The leather gets an amazing patina over time, so it’s a treat to watch them evolve. You can see my pair after 100 wears here. Since I bought mine, they also introduced the Zind in burgundy. I have not been able to see this leather wear in myself, but it’s definitely striking.

The Sienna is another great option and can be had for $212.

Nicks Handmade Boots

For labor day 2023, Nicks is offering 15% off ready to wear, 10% off limited run leathers, and 10% off 365 stitchdown. I’ve been following Nicks for a long time and this is one of (if not the) the best deals I’ve ever seen from them.


My personal pick would be the Natural Chromexcel MTO for $521. I bought mine for full price and absolutely love them, check out the review here. Another option is Wickett and Craig for just $639. It’s getting hard to find anything from the PA-based W&C for under $700, so that is a spanking deal.

Oak Street Bootmakers

Oak Street Bootmakers, or OSB as they are often called, are running an “up to” 30% off sale for labor day. Prices as marked. While not quite as bit as some of their other sales, it applies to everything on their site – including limited editions.

Regular readers know that I have to recommend the natural roughout camp moc for $208. If you prefer something a bit more substantial, you can also get the excellent field boot in natty rough out for $362.


Parkhurst has used Labor Day as a reason to restock their factory seconds. The good news is that there are a lot of choices. The bad news is that they are almost all exclusively in the 8.5-9.5 D range. If you’re not that size, they do have several Allens in Rust Waxy for $278.


Rancourt is offering 35% off for Labor Day 2023. While the selection is limited, this matches their best Black Friday deals, and comes in only slightly less than their pre-order deals (which can take months to receive). Prices as marked.


Personally, I like the Eggplant Honcho boat shoes for $201, though you can also get it in Natty CXL if you want something more traditional. You can also take a look at their Eastport Penny loafer for $206 if you want something a little bit more formal.

White’s Boots

White’s is offering 20-25% off their goodyearwelted line of footwear. While not quite on the same level as their handsewn offerings, they start at around half the MSRP right off the bat, and with this discount they come in at less than a pair of Redwings. Hard to argue with that!

The Perry is likely the one that most people will be interested in – available in 6″ for $260 and 8″ for $268. I’ve also personally always liked the upgraded Timberland vibe of the Chore Boot, listed for $273.