Watch Band Hole Punching in Manhattan

Your best cheap/free options in Manhattan (assuming a leather or similar strap that takes punched holes):

Watch shops (often free or $5–15)

The Diamond District (W 47th St between 5th & 6th) is packed with people who do this in minutes.

• Manhattan Watch Service — 42 W 48th St #1702 (near Rockefeller Center). One customer had extra holes punched in an alligator strap and they didn’t charge. Fast and friendly.[1]
• Restoration Watches / Mark Livak — 15 W 47th St, Booth 57-58. They explicitly do strap sizing/adjustments.

Walk into almost any jewelry or watch booth on 47th Street and ask. Many will punch 1–2 holes as a courtesy or for a few dollars.

Cobblers / shoe repair (usually $3–10, sometimes less)

They punch belt holes all day long — same job, 30 seconds.

Any neighborhood shoe repair shop will do it. A well-known one is Jim’s Shoe Repair at 60 E 59th St.

DIY (~$10–20, you keep the tool)

Buy a revolving leather hole punch (the kind used for belts) at Home Depot:

• 40 W 23rd St
• 410 E 61st St

Or get a cheap watch-strap punch pliers delivered same-day via Amazon.

Other quick notes

• If it’s a luxury brand (Cartier, Omega, etc.), try their boutique first — they often size straps/bracelets.
• Take the strap off the watch if possible (safer and easier).
• If the current band isn’t special, a new inexpensive leather or NATO strap is often cheaper and faster than modifying a bad-fitting one.

Start with the 47th/48th Street shops — highest chance of it being free or nearly free while you wait. Tell them you just need one or two extra holes to match the existing ones.