the worn out shoes

[angliholic]

Tom is so economical that he hurts throwing away his worn out shoes.
Tom is so thrifty that it hurts him to throw away his shoes which are worn out.



Do both of the above sound right? If not, how would you reword them? Thanks.

[Naamplao]

Tom is so economical that he hurts throwing away his worn out shoes.
Tom is so thrifty that it hurts him to throw away his shoes which are worn out.

Do both of the above sound right? If not, how would you reword them? Thanks.

The second is the better version but I would reword it slightly.

Tom is so thrifty that it hurts him to throw away his worn out shoes.

[angliholic]

Thanks, Naamplao.

[joham]

Tom is so economical that he hurts throwing away his worn out shoes.
Tom is so thrifty that it hurts him to throw away his shoes which are worn out.



Do both of the above sound right? If not, how would you reword them? Thanks.

Worn out shoes should have been worn-out shoes, but these days people tend to drop the hyphen "-":
The following phrases come from the latest dictionaries:
OALD 6th edition: worn-out equipment; worn-out old cliches
LONGMAN 4th edition: old worn-out walking boots
MACMILLAN: dirty worn out shoes

Other attributive phrases that should have had hyphens: (from OALD6)
mind: It's make your mind up time.
large: He's a larger than life character--noisy, very friendly and always
joking.
think out: It's a well thought out plan.
expense: an all expenses paid holiday