Old New York Gem
I just wrapped a long weekend in a Grand Luxe room at the St Regis. Our little family of four (2 kids under 6) fit easily in the vaulted, beaux arts chamber, and even into the generously sized double beds.
Jacob Astor would feel right at home in any of the gilt-bedecked, chandelier-lit rooms. What you give up in modernity, you get back in an indescribable feeling of participating in history, not unlike taking a weekend holodeck visit to the roaring 20s. My two girls were positively awestruck the minute they hit the lobby, and the room sent them over the top. It's the "princess" reaction Disney aims for, and will always fall short of, because there is nothing like the real thing. That classic feeling permeates the whole hotel, from the tuxedoed butlers, to the clubby King Cole Bar, to the silver and china breakfast in the Astor Court. The unrelenting sophistication can make you feel perpetually underdressed in anything short of ball attire, but never uncomfortable.
Sure, there are shortcomings. The phone "control" system is a total trainwreck, the TV remote was rubbed unreadably clean, running the hairdryer destroyed the TV reception, the butlers were sometimes unreachable, the $800/nt room had a view of an HVAC, there was only one robe, there is no lobby lounge area, the doormen seemed to run hot and cold, and the furniture was a little wobbly. Management was totally unaware of a massive, 5-hour long (and very, VERY loud) party on the floor - but was quick to react when notified. I wouldn't want to pull a late night working out deal documents at the Louis XIV desk and matching straight-back chair, either. 
I could see why someone might criticize the ol' gal when compared with a nice new sparkly glass tower at the same price point - especially if one was on business. But for a family or romantic getaway, you wouldn't come close to the transporting experience of the St Regis. So much of the best of NYC is within walking distance of 55th and 5th, you might not even need a cab. (And speaking of transportation, the Bentley house car wasn't too shabby, either, driven by one of the nicest employees at the hotel.) 
We will definitely be back.