Windows comes with several font families (typefaces) that are made up with more than 4 fonts, so such family comes with more than just Regular, Italic, Bold, and Bold Italic. To name a few; Calibri contains 6 fonts, Segoe UI comes with 12 fonts and Sitka is king with 24 fonts. The trick to make this work is fairly straightforward; however you need to be consistent. All fonts within the family must have the same Typographic Family. However the four common fonts (Regular, Italic, Bold, and Bold Italic) leave the Typographic Family and Typographic Subfamily empty, and instead will use the Font Family and Font Subfamily fields. The other fonts will be grouped together based on their Width and Weight, and will get their own Font Family name based on that.
Older software (including Microsoft Office on Windows) supports the combination of Font Family and Font Subfamily, while modern software (including Adobe Illustrator and Microsoft Office on Mac) uses Typographic Family and Typographic Subfamily.
For example a typeface named "GreatFace" with 10 fonts:
In FontCreator all these settings and flags can be modified through the settings on the Font Properties dialog.
Some versions of Windows and Word automatically add fake bold to any font with weight set lower than 250, e.g. Thin or Extra-light (Ultra-light), so better avoid these weights.
If the Typographic Family and Typographic Subfamily fields are empty, the values from Font Family and Font Subfamily are used.
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