Hard to say for me. I don't have anything that I would consider irreplaceable, except for a pocket watch that belonged to my great grandfather and is engraved with his initials. It's just a Bulova, but obviously has great sentimental value. Of course, it's not clothing.
As for clothing, I'd probably choose from:
- Bill's 15th Anniversary khakis
- Alden Indy Boots (I just love 'em)
- Polo shell cordovan chukkas
- LL Bean leather jacket - I just bought it last year and there's nothing particularly special about the make, but I had one like it all through college and law school (which I gave away once I lost weight and it got too big on me), so there's some sentimental value there
- Oxxford cashmere sport coat
I guess I'd go for the Oxxford - it would be the hardest to replace from a monetary standpoint. Besides, if I lost all of my shoes, my wife would have to let me buy new shoes.