I find the 3M 8511 a good option on larger faces. It does have an exhalation valve, which makes it rather comfortable. The design has the straps attached a little bit inside of a perimeter edge - that means there is usually less discomfort from the edge digging into the face (since it is spread over more surface area).
Another option is 3M 8233. It is an N100, so it exceeds N95 standard and is more of a niche product in the safety world (most users in N100 will just upgrade to a reusable cartridge-style product). It’s going to cost more (probably closer to $15 each), but is pretty durable and has thick straps with adjustable length. I saw it on sale in 3M Amazon store for about $11 though.
I would generally prefer to buy from an authorized 3M safety/industrial distributor (like Airgas, Grainger, Fastenal, etc in US) instead of Amazon. You will get better pricing and be more confident of the authenticity. (Edited to add: I think it is low risk to buy the 8233 on Amazon. It is tough to counterfeit and available through 3Ms authorized store)
8511 -https://www.airgas.com/product/Safety-Products/Respiratory-Protection/Disposable-Masks/p/3MR8511
8233-3M Particulate Respirator 8233, N100, Cool Flow Exhalation Valve, Adjustable Noseclip, Braided Comfort Strap, Faceseal, General Purpose for Dust and other Particles, Maximum Filtration https://www.amazon.com/dp/B008MCV43K/ref=cm_sw_r_cp_api_glt_i_5KCMTMQH71SE3NX76TS0
I have tried
The Respro is okay. Certainly the only stylish one i tried. One common feature of the masks is a moldable metal nose piece, that allows you to shape the mask to your face. The one on the respro is both the most durable, and the worst. Its stiffness makes it tough to form and reform. That said, the seal it forms seems to be fine, but getting a really good fit is hard, because it lacks a strap that goes over the ear. I'm sure you can get this style of mask in n99 or whatever.
The 3M n95 is the cheapest (by far), and the lightest. The fit is good, and the seal is adequate, although the seal is the worst of the four. The filter is more stiff like paper.
The 3M n100 is probably my favorite so far. The filter is more flexible like cotton. I generally don't worry about crushing it in my bag, except for the metal nose piece. The fit and seal are both excellent.
The 3M p100 is certainly the most hardcore. It's cost is the highest, but the replacement filters are cheap enough. I haven't used it much, but it's the one that the bicycle collective sells, which I consider to be a good marker.
Also I recently reached out to the American Lung Association about masks. Here is the last, most detailed response.
USEPA sets a PM 2.5 annual air quality standard at 15ug/m3 This is a rolling 12 month average. There is also a 24 hour limit of 35ug/m3 These numbers are established for air quality in the air shed and not necessarily in the breathing zone – which is the most item relevant to your question. These numbers are not extractable to breathing zone concentrations. A healthy person should not have a need for any respirators, the respirator is recommended for those with impaired systems. In addition, lung cancer is complex and there are other factors, which include air quality (type of pollutant), genetic disposition, and duration of exposure.
Saying all this, it’s hard to make a recommendation on when to use the N95 disposable respirator to prevent lung cancer (knowing that the three factors above play a large role in the equation and outcome). If in doubt, or if you feel there is a need, wear the respirator (with proper fit) when there are air quality concern days).