In this chapter we identified the design features that assure the effectiveness of the two most crucial e-Shop components: the product catalog and the shopping cart. We presented a set of guidelines assuring a positive shopping experience, as regarded from the customer’s point of view. If one of the primary business objectives is to create and expand a loyal customer base, it is only natural that the customer will keep coming back at the e-Shop when the prior shopping experience from it is positive. And even though in general “positive” may mean different things to different people, for online shopping the scenery is not that vague because customers are driven by a clearly defined purpose. Based on this and a set of principles that derive from the area of human computer interaction and Web design, we investigated the factors that affect catalog and shopping cart effectiveness and explored ways to satisfy them in practice.