Housekeeping
Before we jump into this month’s newsletter, I wanted to quickly plug a recent interview with
Ok, Lets Talk Boots.
This newsletter, like so many that preceded it, started off in a different place. I intended to put together a roundup of all of the boots that are currently in my rotation along with a few that have fallen by the wayside over the years, along with some introspection as to why that might’ve been the case. So many people in fashion advocate for “timeless style” but there’s been plenty of discourse as of late over what that actually means, and whether everyone’s endgame really needs to be a perfect capsule wardrobe. When you are an emotional dresser like me (shout out Jian DeLeon for terming it) it’s inevitable that you’ll gravitate towards certain things and put others on the back burner for a bit. I haven’t cleaned my closet out in a long time - to the chagrin of my wife - but the benefit thereof is that I can come back to things that I may have cooled on for some time and revisit how I can work these old pieces back into my wardrobe.
So that was what the newsletter was supposed to be about.
But then I thought about how Substack always says that I’m hitting my post limit every time I am about to hit send. I decided to just hone in on just two pairs of boots I own and am currently wearing often, and they both happen to be ones that 3sixteen makes as part of our in-house range.
Square Toe Side Zips
I suppose we should talk about these guys first. The Square Toe Side Zips have taken on a life of their own since we first launched them in January of 2024, and it’s been really great to see them as the catalyst to bring so many new customers to the brand. Our previous forays into footwear have always been through partnerships: Deck Chukkas with Quoddy in 2009, a longstanding partnership with Canadian heritage bootmaker Viberg, P404 Boots with Padmore & Barnes (the original manufacturer of the Wallabee), a Snuff Suede crepe wedge loafer with Blackstock & Weber, and a series of Lug Sole Derbies with Sanders UK. Our first in-house footwear was the calf leather mules, designed in house and made for us by a partner factory in Portugal. Once we saw the success of those mules and established a good working relationship with the factory, we decided to try out their real specialty: goodyear welted footwear.
This style is an amalgamation of a 60’s Frye Campus Boot that our lead designer, Wesley Scott, has been trying to hunt down for decades, mashed together with the apron toe detailing he had seen on a pair of vintage Florsheim boots. As far as we know, combining the side zip campus boot idea with a square apron toe hadn’t really been done before and perhaps that is why this style hit so hard (and continues to). We made a video explaining how the design came together. We tried to spare no expense on the construction methods for the boots: from the cork insert to the goodyear welt and the trims, down to the leather itself, we are really happy with every aspect of how the boot came together. We even love the rough-finish rubber sole that makes the boot comfortable to wear and functional in wet weather from day one.
My pair pictured above are a little different from the ones everyone else owns, and that’s because they are an early sample. I have this thing where even after all this time, I don’t like to take too much from the company because I prefer to leave stock for customers to buy. If there’s anyone who has earned a right to take stuff home, it’s me - but I am who I am. The two ways this boot differs from production are the zipper and the leather finish. We started off with a plastic racquet-coil YKK zipper paired with our usual wire pull, which is a zipper that a lot of boots employ. But it didn’t feel right; we decided to switch over to a full metal zipper which I think feels more luxe. The leather on this boot is exactly the same as what’s on production but you might be able to tell that the leather is super shiny. The factory mistakenly gave it a high polish finish, as they tend to do with lots of other shoes they make in the factory - but we had specifically requested the natural matte finish of the leather as it came from the tannery. As soon as we got it we knew something was wrong, but it’s not really something you can undo. I’ve been wearing it with the hopes that it will dull out on its own and while the shine has slightly subsided, it still doesn’t look as good (IMO) as the production pairs. I’ll live.

And here they are in a fit inspired by the owner of a bistro in Paris that I ate at during market week in January. In my last newsletter, I called him the swaggiest dude on earth and I stand by it. David pulled up to take our order wearing silver wire-framed glasses, a dark knit turtleneck sweater, black work pants, a navy apron, and some black shoes. He had two tiny silver hoops in his left ear and had a vintage Heuer on a crocodile strap on his wrist. David took our order with dry, sarcastic wit and even though he did this day and night, you could tell he was having a good time. I think I was immediately struck by the fact that this was his uniform, that the clothes were a part of who he was. Functional and not fussy; the kind of fit that the average person wouldn’t think twice about if they saw him walking down the street, but I feel like a jawnz enthusiast might recognize that he was wearing the best version of everything he had on.
Anyways, I came back and a few weeks later ventured over to the Merz B. Schwanen flagship in NY to try on their merino/cashmere turtleneck. I kinda wanted to buy both the navy and the black but settled on the former for now. I haven’t gotten the piercings yet.
Lug Chelsea Boots
The Square Toes probably get worn once every 2 weeks, but the Lug Chelseas are on my feet 2x a week at a minimum. I remember when we were sketching the design Wesley said “these boots are you in every possible regard” and I don’t know that I disagree. I am partial to pull-on boots vs. side zips; before this pair, my favorites were the 3sixteen x Viberg Aged Bark Roper Boots which I have worn into the ground and are in need of a resole. The spirit of that boot is alive here, at least by nature of the color of the suede we used. Ours are less orange and more tan, but I know that with time they will all converge on a dirty light brown color that looks incredible. That’s what I love about suede boots - like denim, they really do get better the more you thrash them.
We wanted to give the shoes a more imposing silhouette, so we applied a Vibram Commando with a wedge sole to beef it up. I especially love the toe shape on this boot, it’s not too bulbous but has just the right amount of roundness that I look for. And while it’s not pictured, we made sure to source a tough-as-nails elastic for the gore to ensure that it doesn’t get floppy with use over the years. It’s twice as thick as what I’ve seen on other really nice Chelseas. There’s a lot of talk out there about Chelseas as “brunch boots” but I like to think this particular style is a Chelsea only by name. Nothing slim and pointy here.

These boots match up really nicely with roomier bottoms, so I’ve been wearing them a lot with our vintage wash jeans and our cargo pants. You can’t see it that well but the football jersey under the vest is by All Time High and the numerals are made of hand-selected vintage pennants that were cut up, patchworked together into a big blanket, and then cut into numerals. I had the good fortune of flipping through a few and picking my favorite one because each one is different.
We often get questions about what new shoe styles 3sixteen will add to the mix and whether we’ll be offering our current styles in new leather options (Square Toe in smooth brown leather seems to be the #1 request). Footwear is a tricky game as it takes up a ton of room in storage and when it doesn’t move quickly, you end up sitting on a ton of expensive stock. We’re also subject to manufacturing minimums when we are launching new styles, which is a big risk. The brand has thankfully had way more hits than misses over the years but we’ve found that one of the keys to staying alive has been to move slowly and deliberately. I’m excited to keep growing our footwear offering in the months to come in ways that make sense for us.
black suede hikers PLS
I just reread this because I can’t get the Chelsea’s out of my head. Missed the potential brown side zip 👀. That would solve my debate between the side zips and the lug sole haha.