Walk into any high-end law firm or a creative agency in Manhattan right now and you’ll notice something weird happening at eye level—or rather, ankle level. People are ditching the standard oxfords. They’re moving toward something that looks like a boot but wears like a formal shoe. We’re talking about men's high top dress shoes.
It’s a polarizing look. Some traditionalists think anything that covers the ankle belongs on a hiking trail or a basketball court, but honestly, they’re missing the point. The modern dress boot, or high-top dress shoe, bridges a gap that low-cut shoes just can't touch. It offers a certain "weight" to an outfit. It feels substantial.
I remember talking to a bespoke shoemaker in London who told me that the biggest mistake men make is thinking their trousers should just "sit" on their shoes. With men's high top dress shoes, the trouser break changes entirely. You get this clean, uninterrupted line from the hip to the sole. It’s sharp. It's functional. And frankly, in 2026, it's the only way to survive a slushy commute without ruining your silk socks.
The weird history of the "dressy" high top
We tend to think of high tops as a Nike thing. But if you look back at the Victorian era, the "Balmoral" boot was the standard for formal wear. Prince Albert basically pioneered the look. It was a high-top shoe designed specifically to be worn with morning dress.
Somewhere in the mid-20th century, we got lazy. We decided that "dressy" meant "low-cut." But the high top never really left; it just rebranded. Today, brands like Carmina, Edward Green, and even more accessible labels like Thursday Boot Co. are leaning back into the silhouette. They aren't just sneakers with leather slapped on them. They are Goodyear-welted, calfskin masterpieces that happen to rise above the lateral malleolus.
Most guys get the terminology mixed up. Is it a boot? Is it a shoe? Technically, if it has the lacing system of an Oxford (closed lacing) but covers the ankle, it’s a Balmoral boot. If it has open lacing like a Derby, it’s a dress boot. Call it what you want, but the aesthetic is the same: it’s the "high top" of the formal world.
Why your suit actually needs more leather at the ankle
There is a structural benefit to men's high top dress shoes that nobody talks about. Support. If you’re standing at a wedding or a conference for eight hours, the extra leather around the ankle acts like a soft brace. It reduces fatigue.
Beyond the comfort, there's the "cuff factor."
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When you sit down in standard dress shoes, your socks show. That’s fine if you have great socks, but it can break the visual line of a well-tailored suit. High tops eliminate that. The trouser leg meets the leather, and even when you cross your legs, you maintain a look of total composure.
Material matters more than you think
You can't just grab any leather. If you’re going for a high-top look, the quality of the hide is exposed over a larger surface area. You’ll see the grain more clearly.
- Box Calf: This is the gold standard. It’s stiff at first—expect some blisters for the first week—but it develops a mirror shine that makes a suit pop.
- Shell Cordovan: If you have $800 to $1,200 to spend, this is the play. It’s horsehide. It doesn’t crease; it "rolls." A pair of cordovan high tops will literally outlive you.
- Suede: This is where things get casual. A chocolate suede high top dress shoe with navy chinos? Perfection.
I’ve seen guys try to pull off "dressy" sneakers that mimic this shape. Just don't. The "hybrid" shoe—the one with a sneaker sole and a wingtip upper—usually ends up looking like a compromise that satisfies no one. It’s neither formal nor athletic. Stick to leather soles or slim Dainite rubber soles if you want to be taken seriously.
The "Ankle Gap" misconception
Common wisdom says high tops make you look shorter. People think the high cut "chops" the leg. That’s only true if you wear high-water pants with a contrasting shoe color.
If you match your trouser tone to your shoe—say, charcoal pants with black men's high top dress shoes—you actually look taller. The eye doesn't stop at the ankle. It travels all the way down. It’s a trick stylists have used for decades, yet most guys are still afraid of the boot because they think it’s too "clunky."
Nuance is everything here. A sleek Balmoral boot has a profile just as slim as an Oxford. It’s not a Timberland. It’s a precision instrument.
Real-world styling: From the boardroom to the bar
Let’s get practical. How do you actually wear these without looking like you’re wearing costume gear from Peaky Blinders?
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First, look at your hem. Your trousers need a "slight break" or "no break" at all. If your pants are too long and bunch up around the top of the shoe, you look like a kid wearing his dad's boots. You want the fabric to just kiss the top of the leather.
Second, consider the lacing. For a truly formal vibe, the laces should be tight. Slack laces on a high top scream "I'm heading to a grunge concert."
The Friday afternoon pivot
One of the best things about men's high top dress shoes is how they handle the transition from professional to social. A pair of brogued dress boots works with a grey flannel suit at 10:00 AM. But at 6:00 PM, you can ditch the tie, swap the suit jacket for a leather bomber, and the shoes still make sense.
Try doing that with a pair of patent leather tuxedo pumps. You can't. The high top is the utility player of the footwear world.
Maintenance: The "High Top" tax
Owning these requires a bit more effort. There’s more leather to condition. More surface to polish.
You need cedar shoe trees, but specifically boot trees that have a higher neck. This preserves the shape of the ankle support. If you use standard shoe trees, the upper part of the boot will eventually collapse and look slouchy.
And for the love of all things stylish, use a shoehorn. Tugging at the back of a high-top shoe ruins the heel counter. Once that leather softens and folds, the shoe is basically dead.
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What experts say about the "Power Boot"
Justin Fitzpatrick, the man behind The Shoe Snob, has long advocated for the dress boot as a staple. He argues that the distinction between "shoe" and "boot" is largely a modern invention meant to simplify retail. Historically, the best-dressed men were almost always in boots.
There's also the psychological aspect. Wearing a shoe that laces up past the ankle feels like "armor." It changes your gait. You walk with more intention. It’s subtle, but people notice when a man isn't just shuffling along in loafers.
Common pitfalls to avoid
- Over-detailing: If the shoe is high-top, it’s already a statement. You don't need excessive contrast stitching or multi-colored leather. Keep it simple.
- The "Hiking" Sole: Unless you are actually trekking through snow, avoid massive lug soles. They ruin the silhouette of a suit.
- Cheap Zippers: Some "dressy" high tops have a side zipper for convenience. Don't do it. Zippers fail. They look cheap. They break the lines of the leather.
The investment reality
A good pair of men's high top dress shoes isn't cheap. You’re looking at $300 minimum for something that won't fall apart in six months. Brands like Meermin Mallorca offer incredible value at that price point. If you want to go mid-tier, Carmina or Crockett & Jones are the sweet spots.
Yes, it’s an investment. But consider the "cost per wear." A high-top shoe is more durable than a low-cut one. It handles weather better. It stays in style longer because it isn't chasing trends.
Actionable steps for your next purchase
If you're ready to make the jump, don't just buy the first pair you see on Instagram.
- Check the Last: The "last" is the wooden form the shoe is built around. For high tops, you want a "sleek" or "almond" toe. A square toe will look dated immediately.
- Measure your instep: High tops are less forgiving than low-cut shoes. If you have a high instep, look for a "Derby" style lacing (open) rather than an "Oxford" style (closed).
- Color choice: If this is your first pair, go with dark brown (coffee or espresso). It’s more versatile than black. You can wear it with navy, grey, tan, and denim. Black is beautiful but strictly formal or "edge" fashion.
- The Sock Test: When trying them on, wear the thickness of sock you plan to use. Dress boots often feel tighter than shoes because they grip the lower calf.
Men's high top dress shoes aren't a costume. They aren't a trend. They are a return to a time when men’s footwear was built for both the elements and the office. It's about looking like you know exactly what you're doing, even if everyone else is still stuck in their 1990s-era loafers.
Stop thinking of them as boots. Start thinking of them as the most capable dress shoes you've ever owned. The shift in your wardrobe—and your confidence—will be immediate. Change your shoes, change your silhouette. It's really that simple.