Loring fought at the Battle of Sluys in 1340, following which he was knighted for his bravery and awarded a pension of £20 a year. In 1347 he was with King Edward III during the Siege of Calais, and the following year was invested as one of the founding Knights of the Garter. By 1351 Loring was chamberlain to the Prince of Wales, and a member of his council. He accompanied the prince to Aquitaine in 1353, and distinguished himself in the Poitiers Campaign, during which he was "appointed to be in attendance on the prince's person". He was sent back to England after the Battle of Poitiers on 19 September 1356 to report news of the English victory. For his service to the prince he was given an annual pension of £83 6s 8d for life as well as lands in Wales.