The Splurge: To Boot Wickham Pebbled Leather Double Monkstraps – $245 ($350)
It’s a double monk with a little more beef. There’s a real low profile lug sole on these, a cap toe, and the pebbled leather gives them extra texture. Double monks that were destined to be worn with flannel suits in winter, and jeans year round.
To Boot Shoes are made in Italy and almost always look better than good. Designer Adam Derrick’s wheelhouse seems to be taking classic designs and updating their lines and details. Toe shape looks to be perfect. A call to customer service was inconclusive about the welt. Still not cheap by any stretch, but they are $105 off retail through the Gilt owned Park & Bond. Sizes are getting a bit scattered. With all that said…


They are returnable, but you have to pay to ship them back unless you opt for a gilt credit. Got gilt credits from previous gilt group purchases or referrals? Those should work on these too.
Really nice shape but I dont think I could pull of the monk strap/that texture
Monk straps just aren’t for me.
They look good, but just not for me either. Something about the way it looks like a foot version of a straight jacket.
I purchased from To Boot recently and did a pretty fair write up on my site at The Approach in the article about buying new shoes. To Boot is pretty great. I have no complaints and after six months of regular wear everything is still holding up fine. I recommend them highly.
The best part about double monks are the smooth strap of leather over where laces would be. The texture kills them for me.
With the AE McAllisters on sale for this price…forget about it.
I have these and they are EXCELLENT.
I get complimented all the time. They look better in person. And fit extremely well.
I put 100-150, simply because I don’t care for monk straps. I may be the last guy, but give me a closed oxford lace everytime. The pebbled leather is boss though.
Nice shape, but pebble grain ruins the shoe
I hope to own a pair of double monks one day, but based on how the leather looks in this picture, these aren’t for me. There’s also the fact that they’re not Allen Edmonds, which is basically a deal breaker…
I’ve got 2 pairs of To Boot shoes and I love them both. These fit really well when I tried them on but I can’t get past the pebbled texture.
I’d still rather have these….but only if they ever hit a deep sale
https://dappered.com/2012/01/would-you-wear-it-the-dark-subtle-saddle-shoe/
I also really like To Boot’s stuff, whenever I try them on at Nordstrom Rack I am always impressed. Having said that, with the Mercanti’s being $100 cheaper and also made in Italy (and without the pebble grain, which I am not a huge fan of) I think I’ll pass.
To close to Allen Edmonds pricing for me. You can get the Neumora for $285.
Agreed. The texture of these ruins it for me. I’d much prefer the Neumora, and wouldn’t mind paying a bit more for them.
On the fence with these..
i owned a pair of To Boot New York Chukkas that i purchased from off Saks for 60 bucks. Even at that price they weren’t that convincing. soft leather, but shoddy construction. i’d pass on these and go for the “new” AE Neumora, as all ready mentioned above.
THAT’S WHAT IT IS
I have that same revulsion to monks for a while now, and it took me until your comment to pin down what it was. Thanks!
the soles look really thick and the heel has large lugs… is To Boot New York trying to revive the Doc Martins of the late ’90s?
Exactly my thoughts. Like the pebbled leather, don’t like monks.
Honestly, I kind of like the pebbled texture (at least from what I can see in the pictures). I think it adds a little character.
I would buy them in a heartbeat if I needed a new pair of shoes. They’re gorgeous. Cladmen took my money for a pair of Bruno Magli loafers so I’m out of the market for some time.
These look incredible. Love the color, texture and shape. There’s a sense of style, playfulness and originality that a lot of double monks on here just don’t have. It’s a good thing they’re out of my size or my credit card would be taking a hit today…
I tried on some shoes from this company yesterday and was really impressed. I don’t particularly like this particular shoe, especially the pebbled leather, but some of their other offerings are amazing. The ones I tried on were brown and got darker in the toe. Looked really sweet, but were $375 at Norstrom.
ditto – for some reason they just make me really uncomfortable.
Not crazy about the lugs (or monkstraps in general) but I really like the pebbly texture on these. It doesn’t go overboard the way some pebble-textured leathers do.
Gah.. Just about anything that’s made in Italy will cost an arm and a leg. If cereal were made in Italy, I’m sure we’d be paying $50 per box.
The price is right but the month is wrong – if it were late September I’d be reaching for my wallet.
The shoe is ugly to me. Never been a fan of pebble grain leather. And the shoes look awkwardly bulky.
Glad to be of service with regard to creative analogies.
ooo these are nice
Normally I love dub monks and everything about it is fantastic… except the pebbled leather. Ruins it for me.
I own a pair of Adam Derrick’s perf cap toe’s and don’t consider them that good of quality. The leather is very thin, and I can actually feel the cold air when I wear them in cold weather. The heel (inside) is already peeling up after normal use, with shoe trees, and the sole also feels very thin. I would definitely try these on before hand before shelling out anything over $150. Not too happy with the quality for an “Italian” labeled shoe.
http://www.zappos.com/to-boot-new-york-aaron-tan
I own a pair of Adam Derrick’s perf cap toe’s and don’t consider them that good of quality. The leather is very thin, and I can actually feel the cold air when I wear them in cold weather. The heel (inside) is already peeling up after normal use, with shoe trees, and the sole also feels very thin. I would definitely try these on before hand before shelling out anything over $150. Not too happy with the quality for an “Italian” labeled shoe.
http://www.zappos.com/to-boot-new-york-aaron-tan
Italian made monks aren’t cheap? I just got back from Italy and there’s a cobbler in Rome that I stumbled into that will make you a custom pair for 100 euro (about $130 after exchange rate/fees).
I am pissed I didn’t pick up a pair- I found it on our first day there and when I went back they were closed. I’m not really that pissed, because I wound up getting a couple pairs of Italian made tassel loafers for $130. For the 2 pairs combined.
That trip blew my mind- I can’t believe how much we overpay for apparel here
FYI…These shoes are on sale at Bloomingdales right now for 180$ if you can find them.
In person they are stunning with a quality build .