The first of a three-match contest starts at Birmingham's Edgbaston ground on Thursday with the inaugural day/night Test in England.
West Indies have not won a Test in England since 2000, just part of a miserable overall away record during the last 20 years.
They have also arrived without several star players, the legacy of a bitter dispute with administrators and a clash with the lucrative Caribbean Premier League Twenty20 tournament.
England come into the series fresh from a 3-1 home Test success against South Africa.
But former West Indies captain Richards, one of the best batsmen cricket has known, said England had frequently under-performed, citing the hosts' defeat by eventual champions Pakistan in the semi-finals of this year's Champions Trophy one-day tournament as an example.
"Over the years, it’s always amazed me with England,” Richards told Thursday's edition of The Times.
"They never win as much as they should," he added at an event staged by the Lord's Taverners cricket charity.
"I look at the Champions Trophy —- there was no better team for that format but they still fell short.
"England have the right stuff in their teams but then they fall down at some hurdle or just don't jump high enough."
Richards, nicknamed 'The Master Blaster', had some of his best days as a cricketer in England, including scoring two double hundreds in a 1976 Test series where he made 829 runs in total, as well as hitting a match-winning century against England in the 1979 World Cup final at Lord's.
Known for his intimidating presence at the crease, Richards urged Jason Holder's side not to be overawed by England.
"I hope the West Indies team can see that England are beatable," said Richards, who also enjoyed success in English county cricket with both Somerset and Glamorgan.
- 'Hurt' -
Richards, who scored 8,540 runs including 24 hundreds at an average of more than 50 in 121 Tests, was a key member of a West Indies side that dominated the world game in the 1970s and 1980s
As such, watching their decline has been particularly painful for the 65-year-old Antiguan
"It does hurt that the glory days have been lost,” he said.
"I was doing some television work during the Champions Trophy and there was no West Indies there. No West Indies. That’s like saying there would be no Chelsea or Arsenal in the Premier League. That’s how it felt."
Richards added: "I don’t believe that many of the players of the modern day really understand the legacy of West Indies cricket and why they are playing for West Indies and why it matters so much.
"Yes, we had our differences (when I was playing) but what stood us out was when we put on that maroon cap there was a real sense of pride. I want to see that return, I want to see that in this group."
alastair cookEngland vs West Indies 2017England vs West Indies Day-night TestEngland West Indies 2017Joe Rootpink ballSir Viv Richardsviv richards
First Published: August 17, 2017, 5:59 PM IST