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There are 24 clues with the answer 'SHOELESS'
# CLUE
1.
Nickname of Joe Jackson
2.
Barefoot, say
3.
She loses out in socks (8)
4.
Without footwear (8)
5.
Like Fred Flintstone, sartorially
6.
Unfortunately, he loses brogues in the end - so this?
7.
________ Joe Jackson
8.
Barefoot (8)
9.
Barefoot, perhaps
10.
In one's bare feet
11.
Unshod
12.
Not shoed
13.
Not booted
14.
Like baseball's Jackson
15.
Joe Jackson epithet
16.
Discalced
17.
Discalceate
18.
Barefooted
19.
Barefoot
20.
68 Discalced
21.
Barefooted (8)
22.
Chicago White Sox star in Field of Dreams, ... Joe Jackson (8)
23.
With feet on the ground, he muddled along with losses
24.
In bare feet