In 1912, a group of students at an all-female American college get rigged up in the conventional male clothes of the day (there werent many choices, male attire being drearily limited), with hats, cigars and waistcoats
The floppy asymmetry of the hat is suggestive of the period 1927-1932 in particular
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Choose a style with a V-neck or sweetheart neckline and a midi length that hits right at the mid-calf
In other words, in the 40s, this casual dress equaled todays jeans, leggings, and joggers that are so popular and worn everywhere all the time