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Differences

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Windsor Outline

Windsor Outline

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.
Top serif
The top stroke of the upper-case 'C' has a vertical or angled upward-pointing serif.
Serif
The upper-case 'G' foot has a forward pointing spur or serif.
Double
The top vertices of the upper-case 'M' have symmetrical double-sided serifs.

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

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Orlando

Orlando

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.
Diamond
The dot on the '?' (question-mark) is diamond-shaped or triangular.
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 top serif
The top stroke of the upper-case 'C' has no upward-pointing serif.
No-Spur
The upper-case 'G' foot has no spur or serif.
Single
The top vertices of the upper-case 'M' have symmetrical single-sided serifs.