From your list;
- asthma rescue inhaler - keep it.
- pens - reduce to one. But if you can't live without color, get the type that has 3-4 color in one. Check out the stationary store that sell Japanese pens. You can customize the colors combo as you wish. They also have cuter case.
- pads/'pons - carry only one or two. You don't need more than that to survive through the day. Or if possible, have a secret stash at work and in your car. Carry only one with you. If it really happen, that one can buy you time for a while til you find the nearest convenient store.
- makeup (lip balm, lipstick, mirror, blotting papers, small tweezers) - Get rid of the tweezer. Do you tweeze in public? Train yourself to do it at home. Or just leave it in the car or at the office if you really need it on hand. Get a small compact mirror. Or just use your mobile camera as a mirror. No comment on blotting paper since I have dry skin and never need it. Perhaps get a smaller pack? Get a tinted lipbalm that can double as a lipstick. Or just carry only one of each if you really can't help. (I know I carry both a tinted lip balm and lip balm in my bag. I just can't.)
- lotion - get a smaller size or squeeze it in a bag or travel-sized bottle instead. Ask yourself why you need it. If you don't use it, take it out. Leave a small tube at your office and your car. Then, you're covered.
- prescription sunglasses (need these to drive) and glasses (need these to see when not driving!) - I am short sighted.. Get new lenses. There's lenses that can adjust itself to be darker and lighter to transparent according to the light they're in or exposed to. I don't know how it's called in English exactly, but it exists. Ask your glasses store. And just pick a flaterring frame to wear all the time.
- wallet - reduce the size
- notepad - reduce the size
- pepper spray - Keep it.
- small bottle of Tylenol, blister pack of antacid - reduce to carry only 2 to 4 units. I have these in my bags, too.
- iPhone - Keep
- Keys - Keep, but take off what's not necessary. Leave the "need but not use" in your car or office and keep the main one to get access to them close to you.