He was from a gentry family in Holland, Lancashire. In his early military career, he fought in Flanders (including at the Battle of Sluys), and then in Gascony. He was one of the founding Knights of the Garter in 1344. He took part in Edward III's campaign of 1346, and held a command at Crecy.
Around the same time he married Joan of Kent, daughter of Edmund of Woodstock and granddaughter of Edward I. Between 1353 and 1356 he was summoned to Parliament as Baron de Holland.
In 1354 Holland was the king's lieutenant in Brittany during the minority of the Duke of Brittany, and in 1359 co-captain-general for all the English continental possessions.
His brother-in-law John, Earl of Kent, died in 1360, and Holland became Earl of Kent in right of his wife.
He was succeeded as baron by his son Thomas, the earldom still being held by his wife (though the son later became Earl in his own right). Another son, John became Earl of Huntingdon and Duke of Exeter.
{| border="2" align="center"
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|width="30%" align="center"|Preceded by:
New Creation
|width="40%" align="center"|Earl of Kent
|width="30%" align="center" rowspan="2"|Followed by:
Thomas Holland
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