Understanding consumers by examining their characteristics within segments is a key activity for business success. Many apparel businesses use this strategic tool for focusing their promotions efforts and their assortment selections on a group or segment of consumers. For practitioners and academicians, two of the largest and most intriguing consumer segments in the 2000s are Baby Boomers and Echo Boomers (i.e., Gen Ys). The Echo Boomers are the children of the Baby Boomers or the second generation of consumers following the generation of the Baby Boomers. These generational segments represent two of the most affluent consumer groups in the market place. Many retailers and academic researchers are interested in these segments, and although each segment has received some review, limited academic research has examined their apparel shopping behavior. Studies tend to be focused on one generation but not on the comparison of the two generations and their similar or different shopping activities. The purpose of this study was to examine the influences of generational consumer segments, shopping orientation, and specific product categories on the shopping process variables. Data collection resulted in 355 usable responses from Echo Boomers (ages 18–24) and 180 responses from Baby Boomers (ages 46–59). The respondents, for both generations, included three-fourths female and one-fourth male consumers. The primary occupation for Baby Boomers was listed as professionals (53%), while the second most common occupation was listed as homemaker (16%). More than 98% of the Echo Boomers were full time students. Exploratory factor analysis resulted in two shopping orientation variables (i.e., fashionista and experiential). Multiple regression analyses showed that these two orientation factors significantly explained both segments’ shopping process activities (i.e., wait time and try on). In contrast, the generational segment variable showed no significant differences for the shopping process activities. Findings from this study support the previous work place literature that notes similarities between the segments. In this study, age (i.e., generational segments) was not a significant factor in explaining selection activities (i.e., try on and wait time). This finding refutes previous studies that proclaim the differences between the Baby Boomers and the Echo Boomers and provides support for the similarities, not differences, between the two generational segments. With the similarities between generational segments being identified, the differences found with other variables are further discussed. The shopping orientation variable provided more information in explaining consumers’ selection activities than the generational segments. Regardless of age (i.e., generational segment), both Echo Boomers and Baby Boomers in this study, who scored high on the fashionista shopping orientation factor, placed less importance on try-on activities and were less willing to wait for products. The try-on activities variable was also explained by the experiential shopping orientation in comparison to its lack of differentiation with the generational segments variable. Consumers, regardless of age, who rated experiential activities as more important when shopping were the consumers who wanted to try on the products. Denim was the one product category variable, in the conceptual model, that explained try-on and wait time activities. Consumers who placed more importance on denim, specifically the fit, color and styling of blue jeans, were the consumers who were more willing to wait for products to be delivered. This research has a number of implications for practitioners and for academicians. Previous research studies in several fields have noted that consumers may react differently to various situations according to their generational segment (i.e., age grouping). However, the findings in this research showed that other variables from the model in instead of the generational segment were more significant in explaining selection activities of consumers. Because of this finding, academic researchers may want to include multiple variables when examining or comparing generational segments. In addition, marketers and retailers may wish to consider removing the age factor in their presentations and promotions of some apparel products. In this study, these female consumers were more driven by their shopping orientations when selecting products than by their age. In another example of practical application of the findings, retailers who design dressing rooms and have sales staff assist customers should realize that all consumers who are interested in shopping may have varying opinions on trying on products and on how long they will wait for a product. Retailers should not assume that the younger consumer will not want to try on products or that an older consumer will want to take the time to try on a product.