Subjects of Equestria! We are pleased to kick off the Nightmare Night Festivities and the 14th anniversary of the return of our beloved Princess Luna! Join us in celebration!
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DragonMaus
Bronze Bit -
Sapphire -
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.
Cool Crow - "Caw!" An awesome tagger
A Perfectly Normal Pony - <DragonWraith> fish are not for sexual
Not a Llama - Happy April Fools Day!
Magnificent Metadata Maniac - #1 Assistant
Bronze Supporter -
Happy Derpy! -

As @FanOfMostEverything said, nowhere is anything said about when “everypony wore their mane that way” or when the show takes place. Based on the chronology we do have, it was probably only five or so years before the show.
Kandak

It’s mentioned that Fluttershy is a year older than Pinkie Pie. No mention of anyone else’s relative age, as far as I know.
 
That said, Cheerilee still didn’t have a mark when Cheese Sandwich first visited Ponyville, well after the mane six got theirs. She can’t be more than a couple years apart from them in age.
FanOfMostEverything
Derpy! - For Patreon supporters
Cool Crow - "Caw!" An awesome tagger
Magnificent Metadata Maniac - #1 Assistant
Lunar Supporter - Helped forge New Lunar Republic's freedom in the face of the Solar Empire's oppressive tyrannical regime (April Fools 2023).
Non-Fungible Trixie -
Preenhub - We all know what you were up to this evening~
My Little Pony - 1992 Edition
Silver Bit -
Ruby -
Wallet After Summer Sale -

Planeswalker — FoME
Actually, thinking about it, all Cheerilee says is “Yes I know, but honestly, that’s how everypony was wearing their mane back then.” No specific decade was mentioned, and there’s no reason to think that Equestria’s cultural chronology is intrinsically tied with our own.
PwnyPony
Silly Pony - Celebrated the 13th anniversary of MLP:FIM, and 40 years of MLP!
Shimmering Smile - Celebrated the 10th anniversary of Equestria Girls!
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Crystal Roseluck - Had their OC in the 2023 Derpibooru Collab.
King Sombra - Celebrated the 10th anniversary of The Crystal Empire!
A Lovely Nightmare Night - Celebrated the 12th anniversary of MLP:FIM!
Elements of Harmony - Had an OC in the 2022 Community Collab
Non-Fungible Trixie -
Kinship Through Differences - Celebrated the 11th anniversary of MLP:FIM!
Verified Pegasus - Show us your gorgeous wings!

☀Welcome Princess Celest
@Mildgyth  
Rarity is certainly older than the rest of the mane 6 but not by multiple decades implied by the post.  
late 20s early 30s? the rest would be early 20s I am guessing.
 
We could assume ponies are behind the times and this happened in late pony 90s.