You’re standing in a Nordstrom or browsing online, and you see them. The leather looks just a bit richer than the stuff next to it. The silhouette isn't clunky, but it doesn't look like a fragile elf shoe either. To Boot New York shoes have this weird, magnetic pull for guys who finally decided to stop wearing cheap disposable footwear but aren't quite ready to drop a full mortgage payment on John Lobb or Edward Green. Honestly, it’s a sweet spot.
Founder Adam Derrick has been running this ship since the 1980s. He started with a boutique in the Upper West Side. Think about that for a second. In an industry where brands get bought, sold, and gutted by private equity firms every five years, Derrick is still the creative force. He’s the guy obsessing over the "last"—that’s the foot-shaped mold the shoe is built around. If the last is wrong, the shoe is garbage. Period.
The Italian Connection Nobody Tells You About
People see "New York" in the name and assume these are made in a factory in Queens. They aren't. Every single pair of To Boot New York shoes is made in Italy. But "Made in Italy" can sometimes be a marketing trick. Some brands do 90% of the work elsewhere and then slap the soles on in Italy to get the legal label.
Derrick doesn't play that game.
The production happens in small, family-run factories in the Marche region and around Tuscany. We're talking about places where shoemaking is a generational curse and a blessing at the same time. The leather is sourced from top-tier tanneries, often using French calfskin. This matters because cheap leather is heavily corrected with chemicals to hide scars and bug bites. Good leather, like what you find on a pair of To Boot New York Chelseas, has a natural grain that actually breathes.
You’ve probably heard of the Blake stitch. It’s the primary construction method here. Unlike the heavy, bulky Goodyear welt you find on American work boots, the Blake stitch runs directly through the insole and the outsole.
The result? Flexibility.
You can actually walk in these things on day one without feeling like your feet are in wooden casts. The downside, if we’re being real, is that they aren't as water-resistant as a Goodyear welted shoe. If you’re trudging through a slushy Manhattan winter, that water might eventually seep through the stitching. But for a day at the office or a night out? The sleekness of the Blake construction is unbeatable.
The Versatility Trap
Most guys buy shoes for one specific outfit. That’s a mistake. You want shoes that can pivot.
Take the To Boot New York "Shelby" or the "Brandon." These are mainstays. The Shelby is a Chelsea boot that basically defines the category for the mid-luxury market. It’s got that tapered toe that makes your legs look longer—always a win—but it’s not so pointy that you look like you’re heading to a 1960s garage rock audition.
I’ve seen guys wear these with a navy suit and look like a million bucks. Then they throw them on with faded denim and a white tee on Saturday, and it still works. That’s the "Derrick DNA." It’s a balance of American grit and Italian refinery.
Let's talk about the sneakers for a minute. The "Pacer" or the "Burnett."
Sneakers in the $300+ range are a hard sell for some. Why not just buy Nikes? Because these aren't for the gym. These are "grown-up" sneakers. They use the same high-grade calfskin as the dress shoes. The margins are tight on these because the materials are so expensive. You aren't paying for a logo; you're paying for the fact that the lining is also leather, which means your feet won't smell like a locker room after four hours.
What Most People Get Wrong About Sizing
Here is the honest truth: To Boot New York shoes run big. Almost always.
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If you buy your "true" sneaker size, you are going to be sliding around like a kid in his dad’s loafers. Most experts—and guys who have worn the brand for decades—will tell you to drop at least a half size. Sometimes a full size.
Leather stretches. It’s a skin. Over the first ten wears, the heat from your foot and the pressure of your gait will cause the fibers to relax. If they feel "a little snug" but not painful out of the box, you’ve found the right size. If they feel "comfortable and roomy" on day one, they’ll be falling off your heels by month three.
Why the Price Point Aggravates Some People
The $350 to $450 range is "No Man's Land" in the shoe world. It's too expensive for the entry-level guy and "too cheap" for the hardcore shoe snobs who hang out on StyleForum.
The snobs will complain that they aren't "hand-welted." They’ll say you should save up another $300 for Crockett & Jones.
They’re missing the point.
To Boot New York isn't trying to be a heritage museum piece. They are making fashion-forward, high-quality footwear for people who want to look sharp now. You’re paying for the design, the Italian labor, and the fact that you can find them in a pinch at a high-end department store.
Maintaining Your Investment
If you spend $400 on shoes and don't spend $20 on cedar shoe trees, you’re basically burning money.
Cedar trees do two things. First, they soak up the moisture from your feet. Sweat is acidic. It eats leather from the inside out. Second, they hold the shape of the shoe so the "toe spring" doesn't get all wonky.
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You should also never wear the same pair two days in a row. Give them 24 hours to dry out. This simple habit will literally double the life of your To Boot New York shoes.
And for the love of everything, get a horsehair brush. Use it after every wear. It takes ten seconds to flick off the dust and salt. This prevents the grit from acting like sandpaper on the leather's surface.
The Reality of the "New York" Aesthetic
New York style isn't about being flashy. It’s about being prepared. You might be in a boardroom at 10 AM, a casual lunch at 1 PM, and a gallery opening at 7 PM.
Adam Derrick designs for that specific lifestyle. He’s often quoted saying that he wants the shoes to be the most "effortless" part of a man’s wardrobe. That’s why you see a lot of suedes and burnished browns in the collection. They soften the look.
A jet-black oxford is formal. It’s stiff. A dark chocolate suede To Boot New York chukka? That’s approachable. It says you know what you’re doing, but you aren't trying too hard.
Where to Buy Without Getting Ripped Off
You can find these at Nordstrom, Saks Fifth Avenue, and Bloomingdale's. The To Boot New York website also has a robust selection.
The secret? The sales.
Because they produce seasonal collections, you can often find incredible deals during the Nordstrom Anniversary Sale or end-of-season clearouts. Getting a pair of $400 Italian-made boots for $240 is arguably the best value proposition in the entire men's footwear market.
Just watch out for third-party "discount" sites that look sketchy. If the price is $99, they are either fakes or someone is trying to steal your credit card info. Real Italian calfskin has a floor price; you can't manufacture it for pennies.
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Actionable Steps for the First-Time Buyer
If you're ready to jump in, don't just buy the first pair you see. Do this instead:
- Identify the Gap: Look at your closet. If you have nothing but sneakers, buy the Shelby Chelsea Boot in Dark Brown Suede. It bridges the gap between casual and formal perfectly.
- Size Down: Order a half size smaller than your standard Nike or Adidas size. If you have narrow feet, consider a full size down.
- Check the Sole: If you live in a rainy climate (Seattle, London, etc.), look for models with a "Vibram" or rubber lug sole. The leather soles are beautiful, but they are slippery as ice on wet marble and wear down fast in the rain.
- The "Bendy" Test: When you get them, put them on a carpeted surface. Walk around. They should feel flexible. If there is a "crunching" sound or if the leather feels like plastic, check the return policy.
- Condition Early: Use a high-quality leather conditioner (like Saphir) before your first big outing. It adds a layer of protection against the elements that the factory finish might not provide.
To Boot New York shoes aren't just about status. They are about a specific feeling of being "put together" without the stuffiness of old-world traditionalism. They represent a guy who values quality but doesn't have time to wait six months for a custom-made pair of boots from London. It’s the sweet spot of luxury. Once you get the fit right, it’s hard to go back to the cheap stuff.