Lord this will be quite a list for me...
Security satchel and a pack of robusts+lighter in my right pocket on ALL of these builds. Spare cig behind my left ear, lit cig in my mouth unless I need internals. Even then, sometimes I'll suffer. I legit go through 2-3 packs of cigs a shift.
HOS: HOS skirt, armored trench, jackboots, fingerless gloves. All the HOS specific items in my emergency box.
Warden: Warden skirt, Warden jacket, Warden beret, jacksandals, Krav Maga (duh?). Box of cuffs and flashbangs in my bag. Shotgun with tranq darts in my office.
Pilot: EVA with my helmet down as frequently as possible because I look fan-freaking-tastic. Pilot jumpsuit, bomber, beret, and fingerless when not in EVA. Box full of tools and GPS.
Officer: Black officer jumpsuit, armor, jackboots, and fingerless. (I rarely play officer as Tetra tho, I have a snoflek unathi who I usually use as my lemming)
Brig Doc: This one is my fav. Sec jumpskirt, red bandana, jacksandals, fingerless, and the red brig phys vest. I even swap my doctor bag for a sec satchel and take a sec belt for pepper spray, flash, cuffs, and of course an emergency donut. I like to look like I'm part of sec when I'm the doc, not just another doc.
On all of these my sec belt has baton, flash, pepper spray, flashbang, and Ebola. Cuffs in my left pocket. Spare cuffs and fbang in my bag. Sec gas/riot mask. A first aid kit if I can get my hands on one. Oxygen F aid kit with air tank, SBR, emergency fire extinguisher, flare, and other misc stuff.
That covers MOSTLY everything. I never tape my boots cuz I like sounding like AUTHORITY. By never I mean I MIGHT tape them is sec is starting to look thin due to casualties caused by a powerful antag.