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Carlos Santos Shoes: My Derby and Chukka Boot Review

If you appreciate beautifully crafted men’s shoes, you’ve likely come across Carlos Santos Shoes in conversations among style enthusiasts who value timeless design, high quality, and exceptional value. Before you place your first order, especially if you’re considering buying directly from santosshoes.com, there are crucial details you need to understand to avoid costly mistakes.

In this post, I walk you through my firsthand experience ordering, evaluating, and wearing a pair of shoes and boots from Carlos Santos. Along the way, I share surprises, lessons learned, and key wins. You’ll get a closer look at the brand’s background, how it compares to top-tier makers like Edward Green and Crockett & Jones, and why I now recommend ordering through Noble Shoe instead of directly from the Carlos Santos website if you’re a first-time buyer.


A Brief History of Carlos Santos Shoes

Carlos Santos Goodyear Welted Shoes

Carlos Santos Goodyear Welt Process

To appreciate what makes Carlos Santos Shoes so special, you need to look at São João da Madeira, Portugal — a city with decades of shoemaking tradition at its heart.

Carlos Santos began his shoemaking journey as a teenager, learning the craft from Ana Santos, his family’s matriarch, who had worked in the leather industry for years. Carlos quickly absorbed the skills of the trade and eventually took over the family workshop, transforming it into one of Portugal’s most respected luxury shoe brands.

Today, the Carlos Santos factory in São João da Madeira stands as a symbol of years of history blended with innovation. Here, skilled artisans combine traditional hand-finishing techniques with modern machinery to produce each pair. Many of these shoes are made to order (MTO), especially when ordered through specialized retailers like Noble Shoe, which also offers the brand’s signature patina service. This hand-applied finish gives every pair a unique color and depth.

Compared to more expensive luxury shoemakers like Edward Green, whose pairs often cost over $1,200, Carlos Santos delivers comparable craftsmanship at nearly half the price. This positions them in the same price range as Crockett and Jones. Still, Carlos Santos frequently delivers more striking patina finishes and customization options, making them a standout in terms of value.


The First Thought That Got Me Hooked

I had admired Carlos Santos Shoes for a long time before placing my first order. Their reputation for producing high quality, beautifully finished footwear with stunning patinas had reached me through online forums, Instagram posts, and fashion blogs.Carlos Santos Luxury Shoes

Eager to test them out, I ordered directly from their website, santosshoes.com. My first purchase was the Charlie 7991 Chukka Boot in Bosco — an olive-green patina that was so rich and sophisticated that it immediately caught my eye.

However, this is where the learning curve started. I followed the limited sizing guidance on their website and ordered my usual UK Size 9.5. When the boots arrived, they were slightly too large. That’s when I hit the most painful part of the experience: the expensive return process.

How Carlos Santos Shoes Are Made

Carlos Santos Shoes are proudly made in Portugal, crafted in the heart of São João da Madeira by skilled artisans using a careful mix of modern and traditional techniques.

Here’s how they bring each pair of shoes to life:

  • Pattern Cutting: Artisans cut the leather precisely according to the design and last –
  • Closing: They stitch the uppers, reinforce the seams, and prepare the material for shaping.
  • Lasting: The uppers get stretched and molded over the last, which shapes the footbed.
  • Welt Stitching: For Goodyear-welted models, they attach the welt to the upper and insole, allowing the shoes to be resoled over time.
  • Bottoming: They fit and stitch the outsole for durability and longevity.
  • Finishing and Patina: Artisans hand-apply dyes, waxes, and polishes to achieve the desired color and finish.
  • Final Quality Check: Every pair undergoes a detailed inspection to ensure it meets the brand’s exacting standards.

The Painful Return Process

Unlike many online retailers that offer free or subsidized returns, Carlos Santos Shoes provides no return label and does not cover return shipping costs.

To send the boots back to Portugal, I had to pay $120 out of pocket through FedEx — and that was after leveraging a discounted business rate through a shipping vendor I know. Without that connection, FedEx retail pricing would have cost me closer to $250 — almost half the cost of the boots, which retailed for around $450.

It stung. Despite how beautiful the Bosco Chukka boots looked — the casual boot design and olive patina were exactly my style — I simply couldn’t justify keeping a pair that didn’t fit. The financial hit from returning them made me rethink ordering directly from santosshoes.com again, especially without a clear and reliable size guide.


Switching Strategy: Ordering Through Noble Shoe and Herring Shoes

Determined not to give up on the brand, I switched strategies. I turned to two of the most trusted Carlos Santos retailers online: Noble Shoe and Herring Shoes.

Here’s why these two are smarter choices for first-time buyers:
✅ Noble Shoe offers highly detailed last and size guides tailored to each Carlos Santos model, helping you confidently pick the right size.
✅ Both Noble Shoe and Herring Shoes have clear return policies, and in the case of Herring Shoes, they even include a prepaid DHL return label for a small fee, which eliminates the international return nightmare I faced when ordering directly.

With this newfound knowledge, I placed one more order: A pair of black derby shoes from Noble Shoe, part of the Carlos Santos Handgrade Collection, marked down to an attractive $250 USD. Since they were a final sale, I relied heavily on Noble Shoe’s size and last guide, and confidently chose UK Size 9 — and it fit perfectly


Taking a Closer Look at the Derby Shoes from Noble Shoe

Carlos Santos Handgrade CollectionLet’s focus on the black derby shoes I received from Noble Shoe.

The build quality stood out immediately.

  • The leather felt supple yet firm, with a subtle shine that reflected the depth of craftsmanship.
  • The shoes felt balanced, hugging the foot comfortably without feeling stiff or boxy.
  • The stitching was tight, precise, and elegant, clearly reflecting the hands of skilled artisans.

What impressed me most was how wearable they were straight out of the box. Many Goodyear-welted shoes require a break-in period, but these Carlos Santos derbies felt ready for action on day one. I effortlessly paired them with suits, dress slacks, and even dark denim, appreciating how versatile they proved in formal and smart-casual outfits.


Why You Should Trust Noble Shoe

Without hesitation, I now recommend Noble Shoe and Herring Shoes as the best options for anyone making their first Carlos Santos purchase.

Why?

  • They examine each model’s last (foot shape) and provide realistic, trustworthy size conversion advice.
  • They stock standard and made-to-order styles, so you can explore exclusive colorways or configurations you won’t find elsewhere.
  • Even though the derby shoes I purchased were final sale, I felt confident ordering the correct size thanks to Noble Shoe’s meticulous size guide, which saved me from another costly return experience.
  • Both have easy and low-cost return options, even for overseas customers in the U.S.

If you’re eyeing Chelsea boots, double monks, casual boots, or classic derby or Oxford styles, Noble Shoe stands out as one of the best licensed Carlos Santos retailers to work with.


Exploring the Carlos Santos Patina Service

One of the crown jewels of the Carlos Santos offering is its patina service — a process where you choose a unique color or finish that skilled artisans apply by hand. This service is available mainly through the MTO program or select partners like Noble Shoe.

Carlos Santos Shoes Patina Service

Gorgeous Patina/Color Options

Popular patina options include Bosco (olive green), Wine Shadow (deep burgundy), and Guimaraes (navy blue), each of which gives your shoes a personalized, character-rich finish. Unlike mass-produced shoes with uniform color, these hand-applied patinas have variation, depth, and individuality — no two pairs are ever identical. This attention to detail helps Carlos Santos stand out even more from other brands in its price range.


Final Thoughts

Carlos Santos Shoes strike a rare balance of luxury, craftsmanship, and affordability. Compared to higher-priced brands like Edward Green or Crockett and Jones, you get shoes crafted by expert artisans at a fraction of the price, all without sacrificing quality or style.

However, you need to navigate the sizing carefully. My advice?
✅ Avoid ordering directly from santosshoes.com for your first purchase — unless you’re already sure of your size.
✅ Choose Noble Shoe or Herring Shoes for detailed size guides, trustworthy fit advice, and easier returns.
✅ Once you lock in your perfect fit, explore the made-to-order options and patina service — they’ll elevate your footwear collection with a personal touch.

With the right size and a bit of planning, your next Carlos Santos pair will likely become a cherished favorite — one that blends timeless elegance, rich heritage, and true value.