Please refer to the attached sample project and gif file illustrating the wrong behavior. Workaround: private void radDropDownList1_SelectedIndexChanged(object sender, Telerik.WinControls.UI.Data.PositionChangedEventArgs e) { this.radDropDownList1.DropDownListElement.EditableElement.TextImageRelation = TextImageRelation.TextBeforeImage; this.radDropDownList1.DropDownListElement.EditableElement.ImageAlignment = ContentAlignment.MiddleRight; } If you select the already selected item, the image alignment is returned back to default value. You can find below how to deal with it: this.radDropDownList1.DropDownListElement.EditableElement.PropertyChanged += EditableElement_PropertyChanged; private void EditableElement_PropertyChanged(object sender, PropertyChangedEventArgs e) { if (e.PropertyName == "ImageAlignment" && this.radDropDownList1.DropDownListElement.EditableElement.ImageAlignment != ContentAlignment.MiddleRight) { this.radDropDownList1.DropDownListElement.EditableElement.ImageAlignment = ContentAlignment.MiddleRight; } if (e.PropertyName == "TextImageRelation" && this.radDropDownList1.DropDownListElement.EditableElement.TextImageRelation != TextImageRelation.TextBeforeImage) { this.radDropDownList1.DropDownListElement.EditableElement.TextImageRelation = TextImageRelation.TextBeforeImage; } }