Rypps first appears in the records of Rye in 1449, when chosen by John Hammond†, the newly-elected mayor, to be his attendant and keeper of the keys for the forthcoming year. In the event, he continued to occupy this position for two annual terms. A few days after his appointment, he accompanied Hammond to a Guestling at Hastings, and later on returned there for negotiations to settle the disputes between Rye and its member-port of Tenterden. It seems likely that Rypps made a living by trading in wine, for he supplied the wine which the commonalty gave to a herald sent by the warden of the Ports, the duke of Buckingham.
The two men were elected to the Parliament summoned to meet at Reading on 6 Mar. following, which moved to Westminster for its second session from 25 Apr. to 2 July 1453. The Parliament was eventually dissolved in April 1454, and that summer Rypps received a payment of £3 1s. 6d. towards his parliamentary wages. This did not amount to much for a Parliament which had lasted 160 days all told, and he evidently had difficulty gaining the rest of the sum due to him, for further payments merely dribbled in over the next three years, and were for the most part made in the form of allowances on maltolts he owed on the sale of salt and other commodities. Even then, ten small payments amounted to a total of just £3 12s. 3d. (which meant that, if he had attended all the sessions, he had received less than 1s. a day). It is notable too that it was only when Rypps became mayor that he managed to claw back some of his parliamentary wages.
Shortly after his election as mayor in 1455, Rypps hosted a visit by the lieutenant warden of the Cinque Ports, he himself providing oats, hay and litter for eight horses at the visitor’s lodgings.
Little is known about Rypps’s own property, although as he was one of the 20 men taxed at the highest rate of 3s. 4d. for a half-scot collected in Rye in May 1459, his holdings may have been substantial.
