An only child, Bessie Wallis (sometimes written "Bessiewallis") Warfield was born in Square Cottage at Monterey Inn, a hotel directly across the road from the Monterey Country Club, in Blue Ridge Summit, Pennsylvania.
A summer resort close to the Maryland–Pennsylvania border, Blue Ridge Summit was popular with Baltimoreans escaping the season's heat, and Monterey Inn, which had a central building as well as individual wooden cottages, was the town's largest hotel.

Her father was Teackle Wallis Warfield, the fifth and youngest son of Henry Mactier Warfield, a flour merchant described as "one of the best known and personally one of the most popular citizens of Baltimore" who ran for mayor in 1875.
Her mother was Alice Montague, a daughter of stockbroker William Latane Montague.
Wallis was named in honour of her father (who was known as Wallis) and her mother's elder sister, Bessie (Mrs D. Buchanan Merryman), and was called Bessie Wallis until at some time during her youth the name Bessie was dropped.

According to a wedding announcement in the Baltimore Sun (20 November 1895), her parents were married by C. Ernest Smith at Baltimore's Saint Michael and All Angels' Protestant Episcopal Church on 19 November 1895, which suggests she was conceived out of wedlock.
Wallis claimed that her parents were married in June 1895.
Her father died of tuberculosis on 15 November 1896.
For her first few years, she and her mother were dependent upon the charity of her father's wealthy bachelor brother Solomon Davies Warfield, postmaster of Baltimore and later president of the Continental Trust Company and the Seaboard Air Line Railway.
Initially, they lived with him at the four-story row house, 34 East Preston Street, that he shared with his mother.

In 1901, Wallis's aunt Bessie Merryman was widowed, and the following year Alice and Wallis moved into her four-bedroom house on West Chase Street, Baltimore, where they lived for at least a year until they settled in an apartment, and then a house, of their own.
In 1908, Wallis's mother married her second husband, John Freeman Rasin, son of a prominent Democratic party boss.

On 17 April 1910, Wallis was confirmed at Christ Episcopal Church, Baltimore, and between 1912 and 1914 her uncle paid for her to attend Oldfields School, the most expensive girls' school in Maryland.
There she became a friend of heiress Renée du Pont, a daughter of Senator T. Coleman du Pont of the du Pont family, and Mary Kirk, whose family founded Kirk Silverware.
A fellow pupil at one of Wallis's schools recalled, "She was bright, brighter than all of us.
She made up her mind to go to the head of the class, and she did."
Wallis was always immaculately dressed and pushed herself hard to do well.
A later biographer wrote of her, "Though Wallis's jaw was too heavy for her to be counted beautiful, her fine violet-blue eyes and petite figure, quick wits, vitality, and capacity for total concentration on her interlocutor ensured that she had many admirers."
An only child, Bessie Wallis (sometimes written "Bessiewallis") Warfield was born in Square Cottage at Monterey Inn, a hotel directly across the road from the Monterey Country Club, in Blue Ridge Summit, Pennsylvania. A summer resort close to the Maryland–Pennsylvania border, Blue Ridge Summit was popular with Baltimoreans escaping the season's heat, and Monterey Inn, which had a central building as well as individual wooden cottages, was the town's largest hotel.
Her father was Teackle Wallis Warfield, the fifth and youngest son of Henry Mactier Warfield, a flour merchant described as "one of the best known and personally one of the most popular citizens of Baltimore" who ran for mayor in 1875. Her mother was Alice Montague, a daughter of stockbroker William Latane Montague. Wallis was named in honour of her father (who was known as Wallis) and her mother's elder sister, Bessie (Mrs D. Buchanan Merryman), and was called Bessie Wallis until at some time during her youth the name Bessie was dropped.
According to a wedding announcement in the Baltimore Sun (20 November 1895), her parents were married by C. Ernest Smith at Baltimore's Saint Michael and All Angels' Protestant Episcopal Church on 19 November 1895, which suggests she was conceived out of wedlock. Wallis claimed that her parents were married in June 1895. Her father died of tuberculosis on 15 November 1896. For her first few years, she and her mother were dependent upon the charity of her father's wealthy bachelor brother Solomon Davies Warfield, postmaster of Baltimore and later president of the Continental Trust Company and the Seaboard Air Line Railway. Initially, they lived with him at the four-story row house, 34 East Preston Street, that he shared with his mother.
In 1901, Wallis's aunt Bessie Merryman was widowed, and the following year Alice and Wallis moved into her four-bedroom house on West Chase Street, Baltimore, where they lived for at least a year until they settled in an apartment, and then a house, of their own. In 1908, Wallis's mother married her second husband, John Freeman Rasin, son of a prominent Democratic party boss.
On 17 April 1910, Wallis was confirmed at Christ Episcopal Church, Baltimore, and between 1912 and 1914 her uncle paid for her to attend Oldfields School, the most expensive girls' school in Maryland. There she became a friend of heiress Renée du Pont, a daughter of Senator T. Coleman du Pont of the du Pont family, and Mary Kirk, whose family founded Kirk Silverware. A fellow pupil at one of Wallis's schools recalled, "She was bright, brighter than all of us. She made up her mind to go to the head of the class, and she did." Wallis was always immaculately dressed and pushed herself hard to do well. A later biographer wrote of her, "Though Wallis's jaw was too heavy for her to be counted beautiful, her fine violet-blue eyes and petite figure, quick wits, vitality, and capacity for total concentration on her interlocutor ensured that she had many admirers."
Wallis Simpson