If I chose one clothing option over the other, will it change anything other than the clothes?
If I'm not mistaken, only two scene will change:
1) With Jenna, after the massage in the swimsuit, when she returns to the office, instead of the order to show the breast, we will enjoy the look of her ass;
2) Massage on the couch in front of the TV. In a red dress, you can not massage the back and ass, but it's worth trying only for vanilla relationships, because the breast needs to be caressed

Otherwise, only visually, for example, with the help of Alice's lessons, when she bends over the fallen pen, the nipple will be visible.