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He attended Pratt Institute in Brooklyn, while working for the architect Clarence True. He also studied for three years at the Atelier Masqueray, the first independent architectural atelier in the United States, founded by Franco-American architect Emmanuel Louis Masqueray.

Thereafter, Van Alen worked for several firms in New York, before he was awarded the Paris Prize scholarship in 1908; this led to his studying in Paris, in the atelier of Victor Laloux at the Ecole des Beaux-Arts.
When Van Alen returned to New York in 1911, he formed a partnership with H. Craig Severance. The partnership became known for its distinctive multistory commercial structures. Their friendship grew strained over time and eventually the partnership dissolved. Thereafter both Severance and Van Alen continued to practice on their own in New York.

In the late 1920s, both architects found themselves engaged in designing buildings which were heralded in the press to become the tallest buildings in the world: Severance, 40 Wall Street and Van Alen, the Chrysler Building. At 1046 ft., Van Alen's building won. However, both were surpassed by the Empire State Building in 1931.

The completion of Chrysler building was received by critics with mixed reactions. Van Alen was hailed as a "Doctor of Altitude", and as "the Ziegfeld of his profession." However, the building, itself, was decried by some critics as just flash which "embodies no compelling, organic idea" and which was "distinctly a stunt design, evolved to make the man in the street look up" having "no significance as serious design."

Unfortunately, when commissioned to build the Chrysler Building, Van Alen failed to enter into a contract with Mr. Chrysler. After the building was completed, Van Alen requested payment of 6% of the building's ($14 million) budget - which was the standard fee of the time. After Chrysler refused payment, Van Allen sued him and won, eventually receiving the fee. However, the lawsuit significantly depreciated his reputation, as an employable architect. His career effectively ruined by the lawsuit, followed by the Great Depression, Van Alen focused his attention more on teaching sculpture.