The impact of social media on the eagerness to undergo aesthetic breast surgery is unknown. We aimed to evaluate the association between Instagram engagement and the willingness to undergo breast augmentation. Women aged between 19–34 years old participated in an online survey. Of the 1560 respondents, 1226 (78.59%) met the inclusion criteria. BMI, bra type, bra cup size, education, and level of activity on Instagram increased the willingness to undergo breast augmentation (OR = 1.520, p = 0.020). Moreover, concurrent Snapchat use (OR = 1.348, p = 0.024) and the number of published posts on a respondent’s Instagram accounts (reference, n > 26; 0 < n ≤ 26; OR = 0.708, p = 0.009; lack of posts (n = 0): OR = 0.702, p = 0.155) were significant drivers of the respondents’ willingness. Fashion (OR = 0.730, p = 0.021), design/architecture (OR = 0.730, p = 0.022), and models (OR = 0.623, p = 0.004) were the searched content categories that increased the desire for breast augmentation. Positive and negative feeling scores that were triggered by Instagram content were correlated with BREAST-Q scores. We concluded that Instagram is a commonly used social network service among young women, and it may drive a desire for breast augmentation. Further analyses of Instagram preferences may help assess the willingness to undergo breast surgery, and in turn assist in tailoring marketing campaigns.