To think names considered trashy 20 odd years ago could reemerge as classy name choices in the late 2020s?

No. A slightly tacky name will always remain that way.
Children with surnames as first names in the American fashion ditto.
Odd trendy names likewise will always be odd fundamentally.

Names go in and out of fashion. But some are classic and have lasted the test of time for centuries. Elizabeth etc. Whereas Chardonnay will not. Nor would Brandon as opposed to James.

My Grannie, who would be over 100 now, thought my daughters’ names were trashy. They are what you would think of as ‘old lady’ names, in the style of Florence and Mabel. She thought they sounded like cleaning ladies.

All these names that people say will never be back - they will, of course they will.
When I was growing up in the late 70s/early 80s I would have laughed at a Violet, Ivy, Mabel, Arthur, Alf as being old-fashioned ugly granny/grandad names. Now they are popular and everywhere.
My class peers were Darrens, Lees, Garys, Sharons, Debbies. As we approach the age where we might start to become grandparents, I expect these names will start to appear again. Many people like to name babies after grandparents, and that trend continues. Of the youngest children I know, there is a Lee, Ian and Susie!

In the school I work at there are 2 Martins and a Kevin. There are also more than one Eric.

Lindsay is a tradition Scottish boys name that is still used in Scotland. See also: Leslie. But hopefully the English will stop using them for girls.

Named after a family member maybe ?
Although i wouldnt give it as a first name.

Marie-Chantal anyone? She’s done far better in life than any of us, despite her name.

So that's Gaz, Shaz & Daz.

If Simon Cowell chose “Eric”…

I know a young boy called Derek. It still blows my mind that his parents chose that name.

I think some names will come back
But i think some names are definatley of a time
I cant see Darren , wayne or Lee ever really making a comeback
Or Lorraine , Lyndsey , Keeley either

I hope not! I mean, I entirely admit that I was horrified when my nephew's name was announced (his name is very much a 90's name, and is a 'naughty' name). While working in schools, I was taken aback coming across occasional children with names like Derek and Yvonne, so I'm not sure that names like Tracy and the likes will come back as "classy".

I think that, for as long as there are generations alive who remember certain names in their hey-day, there will always be a lot of, "Are they REALLY calling their baby that?!"

I think the truly posh use either Royal names or names from Greek or Roman mythology and that's always been the case. For names to come back around into fashion I thought it was about 100 years, so when the generation that had those names are dying out and the names become unusual again.

I think the truly posh don’t pick names that are out there. Boys are named after kings or apostles. Girls have a bit more freedom but not all that much. “Jane” is a much smarter name than “Persephone”.

In every generation the cool retro names that parents give babies are the names of their great grandparents. The parents of the parents (babies' grandparents) are then horrified because these are the old boring names their own grandparents had.

It's kind of the same with fashion: 20 year old students in town wear the same tall white socks as my 70yo FIL, and I am watching this horrified down to my tiny colourful trainer socks.

I'm mid 40's and went to school with quite a few Chantelle's.... they were generally quite trashy tbh!

Some could. Courtney and Brittany were nowhere then everywhere then nowhere again so could come back.

Logically, the next fashion should be for 1940's and 50's names.

I think Valerie will be the next Olivia.

The cycle for names is much mich longer than 20 years. Maybe Chantelle will be all posh at one point but it’s a long way off. Names like Linda or Terry won’t be used for babies for decades yet. I think Maddison etc might be ready for a rethink in like 70-80 years.

I don't actually think of that name as trashy. I know a Chantal and a Chantelle, both in their 40s and extremely professionally impressive, so that's my association!

Some of them, maybe.
The ones that just fell out of fashion because they became too popular will likely reemerge; the yoonique, ridiculous and misspelt (like Maddison!) may stay confined to history.
Can’t see Chardonnay, Abbeygayle or Neveah having a big resurgence.

My granny (born 1913) was Violet, “Vi”… glad it’s back after a period of naffness!

Names outside the classic: Elizabeth, Catherine, Ann, Mary, Caroline, Alice, Isobel, Jane/Joan, etc, come and go as fashions change:

Elsie, Ethel, Mabel, Grace (my gran's era) b 1912

Shirley, Patricia, Sheila/Shelagh, Joyce, Barbara, Anita (my mother's era) b1936

Tracey, Sharon, Debbie, Julie (Amanda, Heather, Emma/Sarah/Mary-Jane (or Ann) at the posher end (my era) b1960

Milly (short for many names), Phoebe, Imogen, Holly/Molly, Lucy (dd's era) 1998

What goes round comes round.

I suspect that when my grandchildren arrive, I will be that granny who says “But you can’t possibly call a baby Keith”.

Is it just the one name Chantelle or do you have any other examples?

Anyway, I don’t think it’s changed. Didn’t sound classy 20 years ago and still doesn’t.

The uber Posh I know are unworried about names & if not going trad are happy to pick cool names like ‘Jessie’ & don’t have any ‘middle class’ squeamishness about it being “Jessica” on the birth cert.