The Times in those days was filled with advertisements for department and women's apparel stores. Around 1960 those included Macy's, B. Altman, Arnold Constable and Bergdorf Goodman. Perhaps the ads Caplan touted the most were from Lord & Taylor, featuring the illustrations of Dorothy Hood (1902-1970). Not surprising, because Hood had been at the top of the New York fashion illustration world for a long time and was still going strong.
There seems to be little about Hood on the Internet, but some biographical information can be found here and here. The latter source mentions that due to a 1950s accident affecting her right arm, she trained herself to illustrate using her left hand ... without noticeably affecting the results.
Most fashion illustrations in newspapers and even magazines in the 1950s and 60s were printed in black and white; run-of-paper color is common now, but rare then. Illustrators usually opted for brushwork and ink or watercolor washes to quickly produce effective views of featured merchandise.
Here are some examples of Hood's work for Lord & Taylor from those days.