How can I better my alertness and looks on days when I take multiple allergy/asthma medications?

Control allergies. Patients with allergies and asthma can have tiredness as a common symptom. Sleep patterns can be disrupted and some older antihistamines cause a lot of drowsiness. Take non-sedating antihistamines, keep your allergies and asthma under good control and get a good nights rest. Some people get allergic "shiners" under their eyes when their allergies are not well controlled.
Take less. Taking less benadryl, (diphenhydramine) Claritin or zyrtec (ie a 1/2 dose) may help... Or eliminating these drugs will help the most. Albuterol, nasal steroids, inhaled steroids, singulair, etc don't make you tired or look bad. If the anti-hystamine drugs bother you greatly consider not taking them, or taking them only on non-work days.