In the doctor's office scene, we see the doctor do a pelvic exam with no nurse in attendance. This is now standard operating procedure, but not as common at the time of this episode.
Don's office is shown to us and is clearly a corner office. The corner office is often the prime office space in a company. Most often, it's a bigger office with more windows for better views of the city, a perk for an executive.
Midge mentions that she's working on a newly invented "Grandmothers' Day" job. Actually, in 1978 President Carter designated Grandparents' Day to be celebrated the first Sunday after Labor Day.
This does, however, represent advertising's influence in promoting new holidays. The greeting card business is extremely profitable.
Menken's Department Store, for whom Sterling Cooper builds its poorly received ad campaign, is probably modeled on Bergdorf Goodman, a high-end New York department store facing a major slump as it entered the 1960's. The store, which marketed itself to wealthy New Yorkers, struggled through the 1960's and 70's until it reinvented itself in the mid-80's. Now owned by Neiman-Marcus, it remains open on New York's Fifth Ave. to this day.
Among the recommendations for advertising Menken's Department Store was a spot advertisement on the "Danny Thomas Show". "The Danny Thomas Show" (later "Make Room for Daddy") was one of a number of comedies focused on traditional middle-class family life popular in the late 1950's and early 1960's. Choice of that particular show, along with the use of in-store coupons, was part of Sterling Cooper's efforts to market the upscale store to the average housewife.
In several scenes, we hear Polynesian-themed music and see Polynesian motifs, most notably in the scene where Don meets Maggie for a drink. Following Hawaii's admission to the union in August, 1959, America's burgeoning post-war interest in Hawaiian music, food and drinks flourished and spread east. This led to the popularization of such iconic drinks as the mai-tai we see Maggie drinking, and the pu-pu platter carried by the waiter, as famous west-coast "tiki" bar/restaurants such as Don the Beachcomber and Trader Vic's saw tremendous growth in business, and numerous immitators.
Near the end of the episode, we see Don on a train going home. He disembarks at the Ossining, NY station. Typically, although young single men lived in Manhattan, married businessmen of this era worked in New York City, but lived in the suburbs of upstate New York or Connecticut, commuting to the city on the train.
In this pilot episode, the creator Matthew Weiner reinvents how the slogan for Lucky Strike cigarettes was invented. Originally, the slogan "It's Toasted" appeared in 1917, not in 1960.