What do I wear for my senior session? It’s such a common question and this post has some great tips to plan what to wear for your senior session! I often tell boys to plan a casual outfit, a dressier outfit and something that speaks to their interests or the college they plan to attend. Accessories like a hat can be a great prop for photos because you can wear it, hold it, or set it down next to you. Riley chose to skip the dressy option, but instead just bring his college t-shirt and a flag. I want your session to be a reflection of your personality, so you feel comfortable!