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There are 27 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.
Without footwear
12.
Unshod
13.
Not shoed
14.
Not booted
15.
Like baseball's Jackson
16.
Joe Jackson epithet
17.
Discalced
18.
Discalceate
19.
Barefooted
20.
Barefoot
21.
68 Discalced
22.
Unprotected below head, with not so much beneath top of shield (8)
23.
Bare-footed (8)
24.
Barefooted (8)
25.
Chicago White Sox star in Field of Dreams, ... Joe Jackson (8)
26.
With feet on the ground, he muddled along with losses
27.
In bare feet