The Santiago — Men's Chukka Boot
The Santiago — Men's Chukka Boot
Size Guide: Fits true to size. Order your standard boot size.
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Highlights
Highlights
Details
Details
Highest Quality Leather
- Buttery soft, only gets better with age
Waxed Cotton Laces
- For a fully adjustable fit
Stacked Leather Heel
- Expertly crafted to last
Goodyear Welted
- Fully resoleable & watertight
Sizing
Sizing
This style fits true to size. Order your standard boot size.
Materials
Materials
- Upper: Full-grain (caramel, desert, denim blue, pomegranate, cemento, onyx, chestnut) or Nubuck (oatmeal, black, mahogany, white) leather
- Lining: Calf skin
- Midsole: Vegetable tanned soling leather
- Insoles: High density memory foam
- Our full-grain and nubuck leathers are of the highest quality and will become more beautiful as they age. Please note that since leather is a natural material, there may be slight color, texture, and grain variations.
Delivery & Policies
Delivery & Policies
Adelante products are handcrafted, Made-To-Order, and delivered to your door within six weeks of purchase.
Adelante offers free shipping on orders delivered to the USA and Canada, and you may enjoy zero sales tax due at purchase. Adelante does not cover any import tariffs that may be charged.
Read our return policy and our shipping policy.


The Santiago — Men's Chukka Boot
Words from the Workshop
“I wear a pair of blue Santiagos on special occasions. They’re the perfect complement to warm Antigua nights.”
- Carlos, Adelante Artisan
- 5 stars: 44 (94%)
- 4 stars: 2 (4%)
- 3 stars: 1 (2%)
- 2 stars: 0 (0%)
- 1 star: 0 (0%)
Great quality
I just received these from the Encore try-ons\returns section. Incredible value for the price. Fit is spot on at true to size. Comfortably snug, gently hugging my foot. Leather looks like it's just itching to patina.I may put some eyelets or blind eyelets in bc I'm a little scared about tearing the leather over time when I cinch the laces tight.
Wide foot gift from above… 5E nice.
Very comfortable and stylish. Finally a good looking shoe that comes in wide widths.
Beautiful shoes, great fit.
I love them
Very well made shoes and extremely comfortable. My only issue with them is the rubber material used for the sole of the heal is very soft and small rocks and glass will stick into it. I take them off when I go in my house but it can make the walk feel uneven until the debris is removed. I wear these most days to work.
I’ve purchased about 10 pair of shoes ( 4 different styles) and have been very pleased.
This pair is extremely stiff…. No “ give” at all ….I wore them one time ….. I will never wear them again
Estos zapatos son preciosos, la calidad del cuero es espectacular, lo que quiero saber es con que cera les hago mantenimiento.
Nice design and fit
My first pair of Chuckas, and second pair of Adelantes. Exceptionally comfortable. I wear this pair of boots every day and everywhere - so good looking (the boots, not me) I have been stopped and complimented on their appearance. Love my Havanas, but these are just amazing.
Perfect fit. A nice step up from square toed boots. Love them! Probably gonna buy another pair!!
The boots fit like a glove! The fitting via Zoom was great, assuring me of proper fit.
The boys are so nice my wife ordered a pair and equally loves them. They are so soft and I get compliments all the time.
This is my 3rd pair. 10E is a perfect fit. Almost no break-in needed
This is my 3rd pair. 10E is a perfect fit. Almost no break-in needed
These shoes are beautiful. I also had a really positive customer service experience that made me feel almost as if Adelante took too good care of me!
I love my boots. They are wearing in super nicely. The color is lovely and the craftsmanship is excellent.
I love my Black Santiago. The weight feels nice and hefty. The construction is beautiful. I nitpick I do have is that my left boot still squeaks 2 months in.
Great shoe. Very comfortable.
Such great classical style with a perfect fit.
The shoes feel great on my feet and look good.
Fit great, feel great.
I'm glad I found Adelante in my search for quality wide boots. The boots are well made and are a great fit. I also enjoyed the information Adelante provides on the person crafting the shoes. Will be looking to order more in the future.
Great boots.
Great business model.
It’s good to know where your money is spent. Transparent company making sturdy footwear.
The Santiago is a beautiful comfortable shoe.
I’ve begun to dress a little nicer these days, just to have the opportunity to wear them.
I love them.
This shoe is extremely comfortable and I enjoy it whenever I wear it. It was my first custom shoe and I could not be happier.
Absolutely stunning! They have to be the best and most comfortably shoe I’ve ever worn. They are so beautiful I’m afraid to wear them! The color and patina of the leather is amazing!!! What Patek Philippe is to the watch world, so is the Santiago to the shoe world!
They were comfortable from the start but required a bit of breaking in for long walks (2 plus miles). I know they’re sold as men’s shoes but I am female—wear them with jeans and dresses. They look great.
Nice look. Great quality shoes. My new light color go to for work outfit.
Well built and fit to size. Comfortable to wear and look great. Have them on most casual days. Spend extra on something that will last a long time.
A great universal shoe built from nice sturdy leather. It does take some time to break in, but now (after a few weeks) it fits wonderfully.
The only thing I would change is the material of the outsole. It is very soft, so when walking around in a city little stones keep on burrowing themselves into the outsole, which can be a bit irritating. Otherwise, great shoe!
Shoes are in my blood; grandfather opened a shoe store in 1927 and his father worked in a shoe factory. Until ordering these boots most of my shoes were AE or Alden. These are beautiful, very very nice leather, well made, and look and feel is high end. Just received my second pair of Santiago's, hats off to the craftsmen and the end product. Looking forward to next spring when I'll order the loafers.
the fit and feel are awesome but the stylish look really makes them work for most any situation