Fashion

The Brown Suede Chukka Boots You Will Wear on Repeat This Season

There’s something about fall that makes you want to simplify. Fewer choices, better quality, pieces that work across situations. When it comes to footwear, that usually means finding one pair you can count on day after day. And for me, that’s always a good pair of brown suede chukka boots.

They're easy, dependable, and versatile. The kind of boots that quietly do their job without needing to be the center of attention.

Why These Boots Work

They don’t stand out too much. And that’s a good thing.

I like boots that don’t make a scene. These just slip into your day without needing attention. The suede gives them a little texture. The brown pairs with pretty much everything I already own — navy, olive, denim, greys. No need to plan.

They’re easy. That’s what matters most. I can walk in them all day and not think about it. No stiff soles, no rubbing at the ankle. Just a shoe that moves with you. Which is more than I can say for most boots I’ve owned.

Three That Made the Cut

I’ve tried a lot of chukkas over the years. Some suede boots men looked good but didn’t last. Others felt great but didn’t wear well. These three from Martin Dingman are different. They’re made in Italy. You feel it when you hold them. Nothing flashy. Just really solid materials, smart construction, and a shape that won’t go out of style.

1. The Espresso Pair

Tuscan Italian Suede Chukka Boots
Image Source: Martin Dingman

Shop $595 $417

This one’s the darkest. Almost black, but not quite. That deep espresso suede makes it easy to dress up without it looking like a formal shoe. The inside lining is glove leather — soft, warm, comfortable right away. No breaking in. No band-aids.

The sole’s rubber, but you wouldn’t know it just by looking. I wear these most with dark jeans or charcoal pants. Clean, simple, reliable.

2. The Whiskey Leather One

Tuscan Italian Calf Leather Chukka Boots
Image Source: Martin Dingman

Shop $595

Not suede, but worth including. The leather is smooth, hand-finished, and has that warm whiskey tone that gets better with age. The shape is the same. The comfort is the same. But it reads a little sharper.
This is the one I’d wear to a casual dinner or to the office. Days when you want to look more pulled together without going full dress shoe.

3. The Earth-Toned Suede

Tuscan Italian Calf Suede Chukka Boots
Image Source: Martin Dingman

Shop $595 $418

Lighter than the others. More laid-back. The earth-tone suede is soft and flexible — easy to wear with tan, green, denim, you name it. This one feels the most like an everyday boot. And I wear it that way.
Same comfort system. Same leather lining. Same reliable sole. Has a softer look that feels right for daytime wear.

Wearing Them Day to Day

How to wear chukka boots? You don’t need to overthink these. That’s the whole point.

They go with jeans, with cords, with wool pants. I’ve worn them with sweaters, jackets, even hoodies. You can dress them up or not. Either way, they just work. Which makes them easy to reach for when you’re in a rush or just not in the mood to figure out an outfit.

Taking Care of Suede

Here’s what I actually do. Nothing complicated:

  • Spray them with suede protector before I wear them out
  • Keep a suede brush handy to clean off dust or surface marks
  • If they get wet, let them air dry on their own
  • Use shoe trees when I remember (not always)

That’s it. And they’ve held up well.

What I Look For

I’ve learned what makes a good pair of brown suede chukka boots. Not just in theory, but something I’ve actually tested.

  • The suede needs to feel soft, but not too thin
  • The inside lining should be smooth and breathable
  • The footbed matters — if it’s not cushioned, I notice by noon
  • The sole should grip but not change the shape of the boot
  • Stitching and structure should hold after months of wear

These pairs check every one of those boxes.

Final Thoughts

These aren’t boots you save for special occasions. They’re everyday boots you live in.

They’re what I wear when I don’t want to think too much about what to wear. Comfortable. Versatile. Solid. The kind of thing that quietly does what it’s supposed to do — and keeps doing it.

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