Brand · American men's footwear

To Boot New York

Italian-made, New York-named — men's shoes born when a cowboy-boot dealer fell for Italian craft.

To Boot New York
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To Boot New York is an American men's shoe brand founded and designed by Adam Derrick — the name carried over from his original store, To Boot, in New York.

Derrick opened a cowboy-boot store on Columbus Avenue in 1979, when the boots were a fad; after the trend faded he travelled to Italy, fell in love with the footwear, and apprenticed at shoe factories to learn the detailed artisanship of men's shoes. He began producing for his own store, a success that drew wholesale orders from Bergdorf Goodman, Nordstrom and Saks Fifth Avenue. All products are made in Italy, and the 'New York' in the name nods to Derrick's view of the city as a global crossroads of fashion. In 2023 Nordstrom's Manhattan flagship expanded its selection of the brand.

The To Boot New York pieces worth knowing

Adelaide Dark Brown Calf Leather Driving Shoe
Original Driver
Adelaide Dark Brown Calf Leather Driving Shoe
A relaxed Italian calf driver that carries To Boot New York’s softest off-duty signature.
$375 at TO BOOT NEW YORK
Aldrin Mid Brown Suede Penny Loafer
Modern Penny
Aldrin Mid Brown Suede Penny Loafer
A suede penny loafer with the clean profile and comfort brief To Boot New York does best.
$450 at TO BOOT NEW YORK
Alessio Burnished Brown Cap Toe Balmoral Oxford
Balmoral Oxford
Alessio Burnished Brown Cap Toe Balmoral Oxford
A disciplined cap-toe balmoral for the brand’s sleek Italian dress-shoe vocabulary.
$450 at TO BOOT NEW YORK
Aidan Burnished Brown Cap Toe Oxford
Business Oxford
Aidan Burnished Brown Cap Toe Oxford
A hand-burnished cap-toe oxford built for the classic business-shoe rotation.
$450 at TO BOOT NEW YORK
Bower Burnished Brown Calf Monkstrap
Monkstrap
Bower Burnished Brown Calf Monkstrap
A burnished single monkstrap with enough character to sharpen denim or tailoring.
$475 at TO BOOT NEW YORK
Bedell Dark Brown Leather Chelsea Boot
Chelsea Boot
Bedell Dark Brown Leather Chelsea Boot
A sleek Chelsea boot that turns To Boot New York’s tailoring instincts into an ankle boot.
$595 at TO BOOT NEW YORK
Belvedere Mid Brown Waxed Suede Zip Boot
Zip Boot
Belvedere Mid Brown Waxed Suede Zip Boot
A refined side-zip boot with waxed suede texture and a sharp almond toe.
$595 at TO BOOT NEW YORK
Augustus Brown Leather Western Boot
Western Boot
Augustus Brown Leather Western Boot
A city-minded Western boot that nods to Adam Derrick’s original cowboy-boot chapter.
$695 at TO BOOT NEW YORK
Bolton Black Velvet Formal Slip-On
Evening Slip-On
Bolton Black Velvet Formal Slip-On
A velvet formal slip-on for the brand’s tuxedo-and-after-dark side.
$395 at TO BOOT NEW YORK
Bolla White Soft Calf Elastic Slip-On Sneaker
Slip-On Sneaker
Bolla White Soft Calf Elastic Slip-On Sneaker
A white calf-leather sneaker that folds elastic-lace comfort into a cleaner dress-casual shape.
$450 at TO BOOT NEW YORK
Brown Handwoven Intrecciato Belt
Woven Belt
Brown Handwoven Intrecciato Belt
A handwoven Italian leather belt that extends the shoe leather story into accessories.
$250 at TO BOOT NEW YORK

To Boot New York shopping FAQ

Are To Boot New York shoes worth it?+

For a fashion-forward dress shoe, many buyers think so. All To Boot New York shoes are made in Italy, and the brand built its reputation by offering that Italian construction and detailed artisanship at a more accessible price than some American "Park Avenue" rivals. If you want a sleeker, more modern Italian look without going to the top of the market, it is a sensible pick.

Is To Boot New York good quality?+

The brand is centered on Italian craftsmanship, which founder Adam Derrick first fell for on a trip to Italy before apprenticing in shoe factories to learn men's footwear construction. Its Italian-made shoes are generally lighter and sleeker than their American counterparts, which gives them a modern feel, though that trade-off in build is part of why opinions on heaviness and durability vary.

How does To Boot New York compare to Allen Edmonds?+

They aim at different buyers. To Boot New York competed against "Park Avenue" brands like Allen Edmonds by offering Italian-made shoes that were lighter, sleeker, and more modern-looking, often at a lower price than American-made equivalents. Allen Edmonds leans into classic American construction, so the choice comes down to whether you want traditional heft or Italian sleekness.

Where are To Boot New York shoes made?+

All products are made in Italy. Founder Adam Derrick learned the craft by apprenticing at Italian shoe factories, and Italian production has been central to the brand's identity and its sleeker, more modern silhouette ever since.

Who is behind To Boot New York?+

The founder and designer is Adam Derrick, who lives in Chelsea, Manhattan. He started out in 1979 with a cowboy-boot store on Columbus Avenue on New York's Upper West Side, then pivoted to men's dress shoes after discovering Italian footwear, building the brand from his New York store outward.

How did To Boot New York get started?+

In 1979 Adam Derrick opened a cowboy-boot store on Columbus Avenue when the boots were a fad in New York. After that trend faded, he traveled to Italy, fell in love with the footwear there, and began apprenticing at shoe factories, eventually producing men's shoes for his New York store "To Boot," which proved a success.

Where can I buy To Boot New York?+

The brand is sold at department stores and boutiques in the United States and Canada, as well as on its own e-commerce site. Upscale retailers including Bergdorf Goodman, Nordstrom, and Saks Fifth Avenue carry it in the US, and Harry Rosen and Nordstrom stock it in Canada.

Why does the brand have "New York" in its name?+

It is a deliberate point of pride. Adam Derrick regards New York as the fashion capital of the US and a "crossroads of fashion" on a global scale, so the name pairs that New York identity with the brand's Italian craftsmanship.

Does To Boot New York offer extended sizes?+

Yes. In 2018 the company began offering extended sizes on its e-commerce website, broadening the fit range beyond what its retail partners typically stock, which is helpful if you fall outside standard sizing.

Have any celebrities worn To Boot New York?+

A few. In 2015 Andy Samberg wore To Boot New York sneakers as a guest on Late Night with Seth Meyers, and the brand has also been spotted on Michael Strahan, Matt McGorry, Corey Stoll, and Jake Robinson at events.