Size & Fit
Choose your sole
All-Terrain Lug sole
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All-Terrain Lug sole
Maximum grip
Grip that doesn’t quit
Deep, self-clearing lugs bite on wet streets and loose ground without feeling clunky.
Vibram Dual Piece
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Vibram Dual Piece
Refined
Classic street comfort
Smoother for city wear with all-day comfort. Resoleable Vibram base.office-to-evening wear.
SLEEK URBAN GRIP
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SLEEK URBAN GRIP
Sleek
City street comfort
Sharp and moves fast. Best for daily pavement, office-to-evening wear.
City Trail Hybrid
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City Trail Hybrid
Road-to-trail
Pavement smooth, trail ready
Mid-depth lugs and a cushioned base bridge city miles and weekend paths.
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CYPRESS — Handcrafted Leather Chukka Boots 5" (13 cm) (Men’s)
🚀 Free, fast, and secure worldwide tracked shipping — delivery in 3–7 business days
Handmade in Greece. Available in Waxed Camel. 6 color options. Versatile chukka with 3 eyelets and a rear pull loop for easy on/off. Free Tsavalas leather balm included. Free personalization.
Features & Build
- (13 cm) top-grain leather upper — clean lines, ready for daily wear.
- 3-eyelet lacing — classic chukka configuration.
- Rear pull loop — quick on/off.
- Handcrafted leather midsole — flexible support that molds to your foot.
- City-Trail Hybrid Sole — provides better wet-street grip than a flat sole and absorbs shock for long wear.
- Breathable pigskin lining — keeps feet dry and fresh.
- Stitched leather insole — added all-day comfort.
- Reinforced stitching — built to last for years, not months.
- Ergonomic build — natural fit without fatigue.
- Resoleable construction — replace the sole when needed.
- Two high-quality sole options — (1) City-Trail Hybrid Sole, (2) Vibram® Dual-Piece Sole with wooden heel + leather midsole.
Why Tsavalas?
You’re not buying mass-produced footwear — you’re investing in individuality and lasting craft. Each pair is handmade in Greece from top-/full-grain leathers that age beautifully. Choose from six colors and request adjustments — we build every pair individually, by people who care. A free tin of our nourishing leather balm is included.
About This Boot
Men’s chukka (13 cm) in premium leather with 3 eyelets and a rear pull loop. Shown here in Waxed Camel. Handmade in Laconia for comfort, durability, and true grip — from weekday city streets to weekend paths.
Personalization & Options
- 6 leather colors available (shown: Waxed Camel).
- Two premium sole options (see selector).
- Special requests/customization welcome.
What’s Included
- 1× pair of CYPRESS boots
- 1× Tsavalas leather balm (free)
Care
- Brush off dust, dry away from direct heat, and apply leather balm as needed.
- Resole when the tread wears down to extend service life.
Let customers speak for us
Tuve problemas con la medida de mi sandalia pero la empresa fue super responsable me ofrecieron otra a coste 0 y además un cupón de descuento por el inconveniente. La verdad lo recomiendo mucho!
Beautiful boots! I love them. My wife from Milan commented on the great quality as well
Cannot recommend this shop enough, I added an extra row of hook eyelets (free) and upgraded to a leather midsole for a very reasonable price, the midsole upgrade probably isn't necessary just a preference.
Build quality is amazing, the stitching in particular is absolute perfection I was very impressed, yet they retain a handmade feel that I like.
The upper leather is about 2mm thick, doubled up in many areas (the heel and toe box feel reinforced which will help them keep their shape) with leather lining all around, these boots will last years you will rarely see such quality of materials in this price range. I recommend the rustic brown leather you need to see it in person it's beautiful.
I'll not buy elsewhere as long as these guys are around, if you are thinking about buying a pair go for it, you will not be disappointed.
You can tell these boots are made to last!
The leather is sturdy and thick but not too much. Nice design and craftmanship too. Feels like very good quality so far.
I had a lot of questions to make about the boots and its customization (vibram sole, black stitching, leather insole) and they answered every single one swiftly and in a very kind way, given my amateurish questions. If you have any questions about any of their items, do not hesitate to ask, the seller was a pleasure to talk to!
Totally recommend, both the item and the seller! :)
I am very satisfied with the quality and style of my new leather boots. Customization was a breeze. I was pleasantly surprised by the craftsmanship and would highly recommend this shop to others! These fit perfectly but will take some time to break in the new stiff leather. I hope they last for years and years to come. Thank you so much!
Beautiful boots! I love them. My wife from Milan commented on the great quality as well
My back-and-forth with Pantelis & George to custom make this pair of boots was a joy, and we put in leather insoles and midsoles, Vibram outsoles, changed the top two holes to hooks, and also changed the upper leather to a less-sand down leather.
Boots fit well and the toecap has some room, and the footbed is comfy out the box.
Pantelis took just 2 days to craft this pair while George entertained my last change requests.
It took 9 days from Greece to Singapore.
I love the look and feel of these boots and definitely recommend others to get a pair.
Although the store is young (launched last year) but the physical shoemaker store is 2nd generation. You see this in the workmanship, my wife likes it too.
Magnifique paire de chaussure, fabrication sérieuse, une fois aux pieds cela devient de vrais pantoufle, merci 👍 pour votre sérieux. Comptée sur moi pour une prochaine commande.
The boots are great value for the price – when I was asked what they cost, people have said they expected more that double.
They are true to size, perhaps a bit narrow at the tip. For the Chelsea boots it might be useful to offer half sizes for the perfect fit, but the leather will also break in and conform to the foot.
Out of the box the leather color was much lighter than pictured, but applying the (included!) wax deepens and darkens the color to match the pictures.
The seller is very helpful, thanks!
Special Design ( in case You like to be special)
Good leather
Very good craftsmanship
Clear and supporting communication
Worth every Cent
I recommend this shop