Vanity sizing has become a popular retail trend and recent work shows it has a favorable impact on consumers. However, as the current research demonstrates, significant variations in sizing standards across retailers mean that consumers are as likely to encounter larger sizes as they are smaller, “vanity” sizes when shopping, highlighting the importance of understanding how consumers react to this potential threat in the marketplace. Across five studies we demonstrate that larger sizes result in negative evaluations of clothing and show that these effects are driven by consumers' appearance self-esteem. Importantly, we also find that instead of unilaterally lowering purchase intent as one might assume, larger sizes can actually increase spending, as consumers engage in compensatory consumption to help repair their damaged self-esteem. In so doing, this research reveals a dynamic and complex relationship between consumers and sizing labels, where shopping can serve to build, strengthen, threaten, and/or repair appearance self-esteem.