Preheat oven to 350 degrees F.
In a mixing bowl, beat butter until light and creamy. Add sugars and beat until well combined. Add oil and eggs, mix to combine.
Add dry ingredients and mix until just combined, dough will be thick.
Using an ice cream scoop, scoop cookie dough and gently roll into a ball shape, and place on the pan.
Once cookie dough balls are on the cookie sheet, prepare your glass with a flat bottom by lightly moistening it with water. Press the bottom the glass into the additional 1/4 cup sugar, and then gently press into the cookie, to make an indentation. Repeat with remaining cookies.
Bake for approximately 9 minutes. Remove from oven and immediately press the bottom of the glass into each indentation again while hot.
Allow to cool completely.