It's always a pleasure when a girl has brothers for escorts. No worries. Of course, families in those days were a lot more sober and mutually protective than may be the case these days. But these were happy and social days for the Strachans.
As the only girl in the family, May was pretty much a princess. My father's caption for this photo is "Flapper" but that was pretty much of a tease. All her life she was as sober as this photo. Not unpleasant, but inclined to take life seriously. Born in August, 1907, she lived to August, 2006. Her dress appears to be silk and embroidered. She and her mother were fond of detachable collars, which helped punch up a wardrobe.
Glenn's pants seem to be a combination of jodphurs, knickers and bloomers! But they seem practical for bicycle riding. Combined with his dark jacket and turtleneck, and given his expression, he seems quite formidable. But a big grin was his normal mode and this is probably an illusion from having to squint into the sun. Born in 1905, he died in 1989. I don't know whose left arm is at the edge of the photo. I see the porch chairs have been turned upside down to keep snow off the seats.
This is June, 1924, if I can trust the back of the photo. My father is looking QUITE the college student, which he was. Very sober and intelligent. (Born 1903, died 1969.) May appears to have a cupcake for a hat. The destination is said to be a picnic.
The back of this photo says "Summer, 1925" but it looks to me like the same time period as the photo above. I don't know what the insignia on my father's jacket might mean. He would look more dignified without a pipe growing out the top of his head. (jokes) May is wearing the same vest as in the photo with Glenn, but a different blouse, more like a school uniform, and less fancy hat. Note the farm dog watching from his niche beside the back stairs.