At his first school (unnamed) he won a prize for the best collection of wild flowers made during the summer holidays. He later went to Malvern House private school at Bramley-on-Sea (where he won a prize for Scripture knowledge), Eton and Magdalen College, Oxford. He represented Oxford University at rackets and won his blue in the doubles with 'Beefy' Anstruther.
He lives at No 6A (3A in Thank You, Jeeves) Crichton Mansions, Berkeley Street*, London, which is a flat (apartment), but he is also a frequent visitor to country houses and cottages, French resorts and New York, thanks to his significant private income. He is generous to his friends.
Described as tall, slim and elegant, he plays tennis, squash (rackets), golf (with a sixteen handicap), darts and rides horses. He has a pleasant, light baritone voice, can play the banjolele but has lost interest and plays auction bridge. He once wrote an article on What the Well-Dressed Man is Wearing for his Aunt Dahlia's paper Milady's Boudoir (in Clustering Round Young Bingo). He is a member of the Drones club.
Despite successfully avoiding any permanent commitments, he is not a confirmed bachelor. He once (probably) proposed to Cynthia Wickhammersley and although she declined they remain friends. He certainly proposed to Bobbie Wickham and Vanessa Cook, although much to his relief later they also turned him down, and was very briefly engaged to Pauline Stoker. He was also engaged many times by accident, thanks to the Code of the Woosters, including to his cousin Florence Craye (four times) and to Honoria Glossop. At least four of these engagements occurred at his Aunt Dahlia's place, Brinkley Court. He even managed to get turned down by Madeline Bassett without actually proposing to her but the threat of a later acceptance hung over him for some time.
No stranger to the magistrates court, he has a policy of giving a false name, such as Eustace H. Plimsoll (of The Laburnums, Alleyn Road, West Dulwich) or Ephraim Gadsby (of The Nasturtiums, Jubilee Road, Streatham Common). He was also once given the alias 'Alpine Joe', to protect his identity.
His greatest ally is his valet, Jeeves, whom he looks on as a sort of guide, philosopher and friend. 'Mr Wooster is a young gentleman with every desirable quality, except one ... the gift of dealing with the unusual situation.' - Jeeves.
Jeeves replaced Meadowes, who was sacked for stealing Bertie's silk socks. (Jeeves Takes Charge)
He spent well over a year in New York after messing up a job for his Aunt Agatha, who then asked him to keep Cyril Bassington-Bassington off the stage. Bertie's apartment was on 57th Street and cost $200 or £40 a month, a lot in the 1920's. (Extricating Young Gussie)
A friend of Bingo Little since their days at Eton, Bertie helped Bingo to pursue many girls and get him out of many difficult situations. These included pretending to be an author of romantic novels, getting soaked, listening to sermons and attending local sports. He also survived two attempts by his Aunt Agatha to get him married off to unsuitable girls before returning to New York to escape her wrath. There he got involved with a bird-watcher, some gentlemen from Birdsburg, and attended an Exhibition. (The Inimitable Jeeves)
He was chased by a swan in Jeeves and the Impending Doom, tried to help a friend in the Inferiority Complex of Old Sippy, played with darning needles and hot-water bottles in Jeeves and the Yule-tide Spirit, sang at an amateur concert in Jeeves and the Song of Songs, looked after his Aunt Agatha's dog in Episode of the Dog McIntosh, fell for Gwladys Pendlebury in The Spot of Art, helped a kid back into school in Jeeves and the Kid Clementina, tried to help Aunt Dahlia retain Anatole's services in The Love that Purifies, tried to buy off his uncle's fiancée in Indian Summer of an Uncle and tried to separate Tuppy Glossop from a dog-girl in The Ordeal of Young Tuppy. [Collected in Very Good, Jeeves.]
Bertie also employed Brinkley when Jeeves resigned (temporarily) rather than be confined with a banjolele-playing Bertie in a country cottage. Here Bertie tried to help his ex-fiancée Pauline Stoker get together with his friend Lord Chuffnell. This led to him being kidnapped, blacking up and having his cottage burned down. (Thank you, Jeeves)
He stayed at Brinkley Court where he tried to bring Tuppy Glossop and cousin Angela back together, get his Uncle Tom to give Aunt Dahlia money for Milady's Boudoir and Gussie Fink-Nottle to propose to Madeline Bassett while trying to avoid giving the school prizes. (Right Ho, Jeeves)
Fearing that a split between Gussie and Madeline will leave him with Madeline, he went to Totleigh Towers to try and effect a reconciliation. His Aunt Dahlia asked him to steal a cow-creamer from Sir Watkyn (for Uncle Tom) and Stiffy Byng asked him to do the same (to help her and her fiancé Stinker Pinker). The presence of Roderick Spode added the fear of violence to his person. (The Code of the Woosters)
He endured the Steeple Bumpleigh Horror while trying to help Nobby Hopwood and Boko Fittleworth while avoiding Florence Craye and Stilton Cheesewright. Edwin the Boy Scout helped things to go with a bang. (Joy in the Morning)
He pretended to be Gussie Fink-Nottle, after he was sentenced to 14 days, at Deverill Hall to keep Gussie ok with Madeline. When Gussie succumbed to a rush from Corky Pirbright, Bertie had to recover a letter from Madeline in Wimbledon. He also helped Corky with Esmond Haddock despite five Aunts on the premises. (The Mating Season)
(He went back to school to learn basic skills like bed-making and sock-darning, but was thrown out for cheating, as told in Ring for Jeeves the one Jeeves story where Bertie does not appear.)
Called to Brinkley Court to help his Aunt Dahlia sell off her paper, he was chased by Stilton Cheesewright, engaged to Florence Craye (again) and tried to steal a necklace. (Jeeves and the Feudal Spirit)
Threatened with loss of privileges (Anatole's cooking) he helped Aunt Dahlia by stealing a painting. A painting. Not necessarily the painting. (Jeeves Makes an Omelette)
Hauled down to Brinkley yet again, he was briefed to keep Dahlia's god-daughter Phyllis from playboy Willie Cream. But she is the step-daughter of Bertie's old school master Aubrey Upjohn and Roberta Wickham was also around, causing trouble in her own inimitable fashion. (Jeeves in the Offing)
He visited Totleigh Towers to heal another rift between Gussie and Madeline but this time without success. He was also involved in stealing a black amber statuette for Stiffy Byng and trying to sell it to a Major Plank. (Stiff Upper Lip, Jeeves)
He tried to help Sir Roderick Glossop by encouraging one Blair Eggleston to propose to Honoria G. Unfortunately this led Bertie into the clutches of the Greasy Bird and his niece Trixie. (Jeeves and the Greasy Bird)
Aunt Dahlia called him in to help Harold Winship in a parliamentary election in Market Snodsbury, but his attempt at canvassing failed. He was also accused of stealing a silver porringer from L. P. Runkle and was very briefly engaged to both Madeline and Florence again. (Much Obliged, Jeeves)
Advised to take a rest in the country, he went to Maiden Eggesford where he became involved in cat-napping, engaged to Vanessa Cook and threatened with violence by Orlo Porter and Mr Cook and with a shotgun. Very restful. (Aunts Aren't Gentlemen)
Without the Option
The name 'Wooster' could be made up from scratch but there's a Wooster Street in Greenwich Village, New York. PG lived in that area for a while before Bertie's first appearance. Is it possible PG had that at the back of his mind when searching for a new name? Or is it a play on the town 'Worcester', which is pronounced 'wooster'? Or even a play on Worcester sauce, the character (allegedly) being based on an earlier character, Reggie Pepper?
(Apparently, and I only found out after I wrote the preceding note, there is some evidence for the Wooster Street theory. Unfortunately even that information comes second hand.)