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Differences

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Windsor Bold

Windsor Bold

Crosses
The upper-case 'Q' tail crosses the circle.
Single
The '$' (dollar) has a single line crossing the 'S'.
Closed
The '&' (ampersand) is traditional style with two enclosed loops.
Square/rectangular
The dot on the '?' (question-mark) is square or rectangular.
Sloping
The verticals of the upper-case 'M' are sloping.
Angled
The top storey of the '3' is a sharp angle.
None
The top of the upper-case 'A' has no serifs or cusps.
Serif
The upper-case 'G' foot has a forward pointing spur or serif.
Double
The foot of the '4' has double-sided serifs.
Sloping
The lower-case 'e' has a straight angled bar.

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Note that the fonts in the icons shown above represent general examples, not necessarily the two fonts chosen for comparison.

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Cooper Black

Cooper Black

Touches
The upper-case 'Q' tail touches the circle.
Open single
The '$' (dollar) has a single line which does not cross the 'S'.
Gap top
The '&' (ampersand) looks like 'Et' with a gap at the top.
Circle
The dot on the '?' (question-mark) is circular or oval.
Parallel
The verticals of the upper-case 'M' are parallel.
Round
The top storey of the '3' is a smooth curve.
Left
The top of the upper-case 'A' has a serif or cusp on the left.
No-Spur
The upper-case 'G' foot has no spur or serif.
None
The foot of the '4' has no serifs.
Horizontal
The lower-case 'e' has a straight horizontal bar.