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Old New Hampshire Logging Trail 

Simple: butt sex in the woods during the day. Only butt sex, nothing else.
I brought Amanda down the Old New Hampshire Logging Trail and she had trouble walking back.

Old New York 

Was once New Amsterdam. Why they changed it I can't say. People just liked it better that way! Often compared to how Constantinople is now Istanbul.
Istanbul is business of the Turks. Who’s business is Old New York?
Old New York by FAT KNIGHT December 26, 2018

New Old Stock 

New Old Stock, or NOS for short, refers to retail items or products that are still technically brand new, but have never been sold for long periods of time. This is commonly due to newer and/or upgraded versions of the same product being released, rendering the older models obsolete. Thus, this makes them old stock. But because they're still technically brand new, unused, unsold products, they are termed "new old stock".

New old stock units are typically sold at a greatly reduced price, since most of the focus and attention is put onto selling the current models. Retailers and vendors will usually have various quantities of new old stock left over from the previous product generation cycle, and will sell them at reduced prices to clear them out in order to accommodate for newer models.
John: Whoa, got yourself a new tennis racket huh?
Brian: Yep, only cost $60.

John: Wow that's a steal! How'd you get it for so cheap?
Brian: New old stock. This particular racket model came out in 2014, so it's been replaced numerous times already with fancy newer models. I figured hey, it's still technically brand new anyway, and tennis racket technology hasn't really changed over the past few years, so why the heck not?
New Old Stock by DeeeFoo January 26, 2018

New Old Fashion

Oops sorry, just got done giving a new old fashion.
New Old Fashion by revbjeff December 28, 2010

Old Man New Balance 

Any 990 and up variation of New Balance running shoes, esp. the 992 or 993 models.
Man that dude was rockin' some Old Man New Balance shoes.

New Old Mullet

A hairstyle in which the hair is buzzed down to 1/8th of an inch, also called "The Obadiah".
"Woah bro, I see you just got the new old mullet I'm impressed, looks good. You probably get all the women now"
New Old Mullet by ThymeKeeper March 22, 2023