85% matchSantoni
Italian-made dress shoes with richer patina finishing
What changes: Higher luxury price and in-house Italian factory
Brand profile
To Boot New York
New York men's footwear label by Adam Derrick, making Italian-crafted dress shoes, boots, loafers and leather sneakers since 1980.
New York CityOrigin
MenswearFocus
Quiet luxuryStyle
$$$$Price
4 brands like To Boot New York like Santoni, Scarosso, Crockett & Jones →
What to know about To Boot New York
Founder still draws every season
Adam Derrick started the label in 1980 with a custom cowboy boot shop on the Upper West Side and still designs the collection himself.
American label, Italian factory floor
Shoes are made in Italian factories from Italian and French calfskin, which is where the high price tier goes rather than into branding.
Range is unusually wide
Roughly 100 styles are refreshed each season, spanning oxfords, derbies, chukkas and dress boots through loafers, drivers, sandals and leather sneakers.
How To Boot New York fits
Overall fit
true to size
Most wearers find To Boot New York shoes run true to size on a fairly standard-to-slightly-narrow Italian last, with some sleeker styles feeling a touch snug in the toe box.
Tip: Order your normal measured size; consider a half size down if you're between sizes or have a narrow foot.
Medium confidence · based on 8 sources
By category
| Category | Runs | Shape | Size advice |
|---|---|---|---|
| Sneakers | slightly large | medium width with a slightly roomy fit | Consider a half size down from your normal size, especially if you have a narrow foot. |
| Boots | true to size | medium width, moderate volume | Stick with your usual dress-shoe size; account for thicker socks with chukkas and dress boots. |
| Sandals & slides | true to size | medium width | Order your standard size. |
| Dress shoes | true to size | medium-to-narrow width with a refined tapered toe | Take your normal size; if you're between sizes or narrow-footed, size down a half. |
Directional fit consensus summarized from public sources with AI — a starting point, not a guarantee. Confirm with the product's own measurements before buying.
If you like To Boot New York
85% match
82% matchScarosso
Direct-to-consumer Italian loafers and leather sneakers
What changes: Lower prices, thinner store presence
74% matchCrockett & Jones
English Goodyear-welted formality instead of Italian sleekness
What changes: Heavier construction, more traditional last shapes
70% matchAlden
American-made shell cordovan takes on the same boots
What changes: Chunkier, casual-leaning, no sneakers or drivers
To Boot New York fit questions
Does To Boot New York run big or small?
To Boot New York fits true to size. Order your normal measured size; consider a half size down if you're between sizes or have a narrow foot. Most wearers find To Boot New York shoes run true to size on a fairly standard-to-slightly-narrow Italian last, with some sleeker styles feeling a touch snug in the toe box.
How does To Boot New York fit?
Most wearers find To Boot New York shoes run true to size on a fairly standard-to-slightly-narrow Italian last, with some sleeker styles feeling a touch snug in the toe box. Overall shape: medium width with a sleek, moderately tapered Italian last.
How do To Boot New York sneakers fit?
To Boot New York sneakers fits slightly large. Consider a half size down from your normal size, especially if you have a narrow foot. Shape: medium width with a slightly roomy fit.
How do To Boot New York boots fit?
To Boot New York boots fits true to size. Stick with your usual dress-shoe size; account for thicker socks with chukkas and dress boots. Shape: medium width, moderate volume.
How do To Boot New York sandals & slides fit?
To Boot New York sandals & slides fits true to size. Order your standard size. Shape: medium width.
Brand facts
To Boot New York is a men's footwear label founded and still designed by Adam Derrick, who began with a custom cowboy boot storefront on Manhattan's Upper West Side before shifting to Italian-made dress and casual shoes. The collection spans oxfords, derbies, chukka and dress boots, loafers, drivers, sandals and leather sneakers, cut from Italian and French calfskin and produced in Italian factories. Derrick refreshes roughly 100 styles each season. The brand sells direct through toboot.com and through US department stores and men's specialty retailers.
- Founded
- 1980
- Origin
- New York City, United States
- Made in
- Italy
- Price
- $$$$
- Focus
- Menswear
- Facts checked
- August 2026
- Styles
- Quiet luxury, Urban prep / Ivy, Minimalist / Contemporary