However, as the contest entered its final five minutes, Lorenzo Insigne levelled things up from the penalty spot after James Tarkowski was penalised due to seemingly stepping on Federico Chiesa's foot and sending the attacker tumbling to the floor inside the area.
The late equaliser brings an end to England's sensational defensive run; however, will leave boss Gareth Southgate with plenty of positives to mull over as the World Cup gets ever nearer.
An emotional prelude enveloped an 82,500-strong Wembley Stadium as those in north London remembered three of footballing's most respected men; Jimmy Armfield, Cyrille Regis and Davide Astori.
However, despite the spirit of two of England's greats being celebrated, John Stones' opening moments seemed anything but, with the Manchester City centre back hesitating on two occasions and affording Italy's Ciro Immobile a chance to continue his high scoring campaign.
But fortunately for the hosts, a combination of the 23-year-old's recovering block as well as an impotent early Azzurri leading line allowed Three Lions goalkeeper Jack Butland to remain untested.
And the bizarrely blunt visiting strike force continued to spurn chances inside the opening quarter, with the Lazio talisman, again, failing to force the Stoke City shot-stopper into action despite latching onto a beautifully delivered cross from the right-hand side unchallenged while six yards from goal.
However, as is often the case, the visitors' lack of attacking prowess came back to haunt them midway through the first half, as England found the breakthrough thanks to a rifled finish from Vardy.
Raheem Sterling forced his way through the Italy defence before eventually being bundled to the floor. But Jesse Lingard's alertness to take the free kick quickly allowed the Leicester City striker through on goal before the 31-year-old found the roof of the net - as he dispatched his right-footed rocket past the advancing Gianluigi Donnarumma.
As the remainder of the opening 45 minutes ticked on, the Three Lions gradually grew into the contest, with Ashley Young's flash just wide of the Azzurri upright inches away from doubling the hosts' lead.
However, as German referee Denis Aytekin brought the first half to a close, Southgate's men trundled into to the home dressing room with a single goal advantage; somewhat arguably fortunate, considering their shaky start.
England 1-0 Italy HT: Shaky start from the hosts who struggled to deal with Azzurri's high press. But Jamie Vardy showing once again how important he could be come the summer. Credit to Jesse Lingard, however, whose brilliant quick thinking made the goal. Interesting 45 ahead.
Following the break, England continued to build their performance, with the opening quarter of the second half seeing the leaders gradually creating an increased number of opportunities. However, aside from a stinging Alex Oxlade-Chamberlain effort from the edge of the area, Donnarumma remained comfortable.
But as the tie encroached the final 10 minutes, Insigne came inches away from undoing all of the Three Lions' good work as the Napoli pace merchant latched onto a cheeky dink in behind the defence.
Debutant Tarkowski was deemed to have impeded Chiesa as the 20-year-old drove into the area, allowing Insigne to step up from 12 yards and smash his spot into the bottom left-hand corner to level things up.
That is the way things stayed, bringing an end to England's impressive run of five games without conceding but offering plenty food for thought for Southgate with two friendlies remaining ahead of their travels to Russia.