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boot day 

It's that wonderful unspoken occurrence where one day, without any warning or pre-planning, a large number of commuters start wearing high boots. Happens every year.. No boots the day before and then "pow" they are everywhere for all to appreciate.
I have to get my knee high boots out of the cupboard this weekend I think Monday might be Boot Day.
boot day by glorydaze May 30, 2017
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Boot day 

Celebrated in most states across the United States, boot day marks the time when the youth of tradition pick their boots for the season. It’s typically celebrated on the second Saturday of October. Exact dates vary by region.
My boots are worn out!

Thank god boot day is coming up.
Boot day by Southern_grandpa October 3, 2025

Re-Boot Day 

Analogous to re-booting your computer, a re-boot day is when you call in sick to re-boot your sanity. It usually involves leaving someone hanging at work that is depending on you, but your brain is so fraged you can’t function any longer.
That F'in Korbegli left me hanging today on our project.

Yeah, he blue screened after the meeting yesterday and said he needed a re-boot day.
Re-Boot Day by Mtbikegeek October 21, 2012

jack boot day 

'Tis a day dedicated to booting people up the jacksie i.e kicking them up the arse. Popular with school children. Also you should note that it can be any day the kicker chooses and they can kick you in the shin if they so wish.
Kid: *runs up and kicks you in the shin*
Kid: Jack boot day. HA HA!
Kid *runs off*
You: WTF?? *hobble home*
jack boot day by Tenna May 13, 2005

toe to toe with a boot on a boot day

Toe to toe with a boot on a boot day (phrase):
To stand your ground or face a difficult person or situation at the worst possible time, when everything is already going wrong. It means dealing with pressure on top of pressure, and still not backing down.
“Everything was already falling apart, and then my landlord started acting tough. That’s when I went toe to toe with a boot on a boot day.”
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