I invited a ton of menswear YouTubers over for drinks and pizza so that I could take the opportunity to drunkenly ask them about their favorite footwear in a little series I’m calling “5 Drinks In.” (Fun fact: I did something similar with the crew at Grown & Sewn for my best Red Wing boots video!)
It turned out that these guys like a pretty wide range of boots and shoes, from loafers to cowboy boots. Some of these are discontinued, limited colorways, or custom made, so they’re not all easily acquired, but there should be plenty of style inspiration for everone here.
[Related: The 11 Best Red Wing Boots You Can’t Buy]
Without any further ado, let’s get started with Barron Cuadro from The Effortless Gent.
1. Barron Cuadro, The Effortless Gent
My current favorite pair of shoes is a pair of loafers sort of Italian style, from a brand called Herring. They’re an English brand, probably my favorite right now.
(As for) boots, the most common pair of boots I wear, at least in the wintertime, are these pretty basic six-inch moc toes from the Chippewa brand. I feel like they’re classic. They look good — just simple black leather moc toes.
Barron’s Pick: Herring Dartford Italian Style Loafer
Herring is a British shoe retailer that sells top English shoe brands like Barker, Church’s, Cheaney and Loake. They also have their own line of shoes made in Portugal and their Dartford is an Italian-style Goodyear Welted, individually hand-patinated loafer.
Chippewa 6-inch Moc Toe
The Chippewa 6-inch Moc Toe is a classic moc with a wedge sole but unfortunately for you, it’s been discontinued. That said, it’s extremely similar to the Red Wing moc toe in Black Prairie Leather.
2. Gabriel Dechter: The Mensch
My current favorite pair of boots in the collection, and it’s hard to say because it always changes, I’m gonna go with my Meermin Chromexcel Service Boots.
So those are great because, honestly, they fit amazingly. They’ve molded to my foot over the past winter I wore them in the snow. We had a very snowy winter in New York, so I got a lot of use out of them and they’ve held up really well and really and lived up to the mantra with boots, so really love those right now.
Gabriel’s Pick: Meermin Chromexcel Service Boots
Gabriel has an in-depth review of his Meermin’s here. Meermin, if you don’t know, are a direct to consumer shoe maker based in Mallorca Spain. Their goal is to make high quality, Goodyear welted boots at an affordable price. Their Chromexcel Service boots are pretty straightforward, with Horween Natural Chromexcel, a British-made commando sole, and overall a sleek, and a rugged but dressy shape.
These were a seasonal offering that are no longer made, but for something very similar, check out Grant Stone’s Diesel.
CJ Cook; Image Source: Instagram
3. CJ Cook: Red Wing YouTuber
The ones I’m wearing are completely custom.
I picked out the leather and sent the leather down to Tennessee and then from there they went to Texas and I designed the boot myself. I drew it out exactly what I wanted and they made it for me. The brand is Planet Cowboy and these are custom; no one can get these.
Oh, and this is Red Wing SB Tanning leather in Granite Boundary. So it kind of takes my love of Red Wing and the Western style and puts them together.
CJ’s Pick: Custom Boots from Planet Cowboy
Nashville’s Planet Cowboy specializes in custom cowboy boots and hats. They also make accessories like belts, buckles, and bolos. They are very picky about the leathers they use and build their boots using traditional techniques.
[More Expert Red Wing Advice From CJ – The Best Japanese Red Wings]
4. Nick – Stridewise.com
My whole website is about boots, so it’s hard to say what my all-time favorite is. I’m waxing lyrically here but I can find a way to love any pair of boots.
At the moment, I’m wearing Red Wing’s new Chelsea boots. This is the Classic Chelsea, and the leather is Hawthorne Muleskinner leather. This is a brand new model from Red Wing — well, it came out in April.
I’ve only been wearing for a couple of weeks but they’re already really dirty, like the patina is pretty wild already on these shoes. Chelseas are really easy to put on, they’re cool, I like them — this is my current favorite pair of boots.
Nick’s Pick: Red Wing Chelsea in Hawthorn Muleskinner
Red Wing’s Classic Chelsea is easy to pull-on and has an unusually rugged, round-toed silhouette for a Chelsea. These ones came in Red Wing’s iconic waxed roughout called Hawthorn Muleskinner, a durable leather that patinas very nicely and is way more resistant to scratches than smooth leathers. That said, these are also available in Amber Harness and Ebony leathers.
[Watch these Red Wing boots unboxed]
Brock: The Modest Man
My current favorite pair of shoes is the Koio Capri. I have two pairs, one is the Capri Bianco with the suede detail and the other one is just the regular Capri in oat milk which is a kind of like an off-white. These are my go-to minimal white sneakers and in my opinion, the best Common Projects Achilles Low alternative.
Brock’s Pick: Koio Capri Bianco and Nuvuola
Koio is a newer sneaker company that ethically sources all of their leather from Italy. In fact, everything from the laces to the box is from Italy, and I did a video investigating their surprisingly ethical approach to leather sourcing. They make very simple, understated shoes that less expensive than Common Projects.
The Oat Milk leather was a limited colorway and is no longer available, but the Nuvuola Bianco is pretty much identical.
[2-Month Koio Sneaker Review – Why Italian Made Matters]
Wrapping It Up
Not surprisingly, these guys had a wide variety of top-notch footwear recommendations. I learned a few lessons, like I might need to pick up a pair of custom cowboy boots. Big thanks to all the guys for hanging out — it was worth the hangover.
Make sure you watch the other entries in this series: