The biggest seasonal changes for me are outerwear and footwear.
EDC when not flying:
- Handgun and reload 
 - Knife (varies based on my plans and what knife is most appealing when I get dressed)
 - Pen
 - Wallet
 - Keys
 - LM Style PS (I used to carry a PS4 but I fly too much nowadays)
 - Phone
 
I leave the handgun and reload behind when going into secured buildings.  I also leave the knife behind (or check it) when flying.  I largely do not check bags so I largely do not bring a handgun or knife when I fly.
My laptop bag is usually with me:
- CoTCCC-based trauma kit (with decompression needle deleted for TSA compliance)
 - Booboo kit
 - Charging and data cables
 - USB battery pack
 - 120V to USB charger
 - Ham radio HT
 - Flashlights and a headlamp
 - Ritter PSP with a Heatsheets 2 person blanket
 - N95 mask
 - Small bag for water
 - Zip ties, duct tape, and a few other odds and ends
 - All manner of stuff to support my continued employment, including my laptop
 
Mission specific loads include:
- Hiking bag (trauma kit, booboo kit, backup knife, multitool, water, room for food) (comes with me to outdoor ranges as well as other outdoor activities)
 - Range bag (trauma kit and range supplies)
 - Bail-out-bag (trauma kit, booboo kit, full-size handgun with reloads, rain shell, ham radio HT, phone charger, backup knife, multitool)
 - CERT callout bag 
 - Computer service bag (I don't do that for a living but sometimes I do favors for friends)
 - Full-size multi-mission emergency kit, one in each car