Hello!
While the above help is indeed excellent, I figured I would throw in my buck-eighty-two for good measure, as additional perspective benefits everyone.
For a couple points of reference on my knowledge base, I've played a Dark Elf for the last 13 years (Ooooold) and have worked in the skin care industry for the last 4. Over those baker-dozen years, I've gone through a number of different 'things' that can impact your application of makeup.
Currently, I apply makeup via an
airbrush system. Now, I know what you're probably reacting with first -- "That sounds way more pricey than I'm looking for". I thought that for a while, as well, but have been using it without much complaint for the last year and change. If you're just starting into a make-up'd race, I would generally agree that an investment into application hardware isn't something to do on a whim, however for anyone set on a heavy-makeup race, this changes a great deal.
- Application Time -- Following May's National event, I've got makeup application down to ~15-20 minutes for neckline-up. That includes hair and ears -- Dark Elf, and all that. We applied the faces for four dark elves well inside an hour with a single airbrush.
- Water Proof and Incredibly Smudge Resistant -- Going into an alcohol based makeup has allowed a freedom of costuming without fear of the dreaded makeup transfer. To the extent that I'm presently donning entirely white for entire weekends without makeup transfer to the collar.
- Consistent application -- Airbrushing is a very even-application. Getting a caked-on look that will happen with other types of makeup is incredibly difficult to stumble into by mistake with an airbrush.
- Stencils -- Yes, Stencils. With appropriate setting powder, you can apply the exact same look every time, ensuring crisp edges and lines if you choose to acquire stencils.
- Clean-up -- The big call after events is certainly that high makeup race folk should go clean the bathrooms or other places they apply makeup, because they make a mess. Well, unless you're spraying this on literally everything around you intentionally, there's little to nothing that needs clean-up. You'll need to clean out the actual airbrush gun, but that's maybe 4 oz. of isopropyl alcohol run through it directly into a drain. Easy peasy.
Now, there's a downside to an alcohol based makeup applied through airbrush other than the cost. It dries out your skin on application, which makes the importance of pre-application of lotion paramount. While applying something with SPF in it on Friday night may seem like a great idea, the reality is that the SPF's exposure to air will, in fact, be long gone by the time Saturday morning rolls around. Going with something that won't irritate your skin, while providing lasting moisture without pushing you into a break-out scenario is what you're looking for, and that's something that no amount of online experience can really convey, what with skin being different on every person.
For the makeup that goes into an airbrush system itself, there's a few out there and I'll admit that I've only explored alcohol-base due to the above non-transference aims and goals. While some will swear by specific brands of makeup, the biggest difference I've found is how new or fresh it is. I've tried
Endura and
Pro-Aiir previously, and while Endura tends to stay 'fresh' a little longer, proper storage is likely the larger key, as with all makeup.
Again, as with all make-up, you'll want to set it. With an alcohol/airbrush setup, the
setting powder is key, as this makeup has a tendency to stick to itself post-application, which can make awkward lines across your skin (especially the neck). Additionally, after an initial pass, I go over 'problem' areas that tend to wear thin or get missed easily an extra time or two, applying setting powder after each pass, and then finishing with a
setting spray.
"Hey, you said some pointlessly huge number of years playing a prohibitively makeup covered race, but only mentioned the last year. What's the deal, guy?"
I'm glad I asked me that question, self. What I was using previously was the oft-mess-making
Mehron Charred Ash specialty powder. This served me well for many, many years, however I spent many, many hours both applying and cleaning up everything around me. And that includes time spent five feet away from the mirror, applying over a large garbage can to minimize clean-up. While this is a great, inexpensive makeup, it does have the clean-up aspect working against it. It does provide some transference-resistence, but still readily noticeable if you plan on wearing anything other than the color of the make-up exactly (And I do mean exactly -- since dark green still transfers to a shade lighter with noticeable ease). As a counter-point to the airbrush 'wash your face thoroughly' above, this specialty powder adheres best to the oils of your skin. Not exactly great for cleanliness, I admit. I've heard some people say use the above setting powder with specialty powders, but I honestly couldn't tell the difference the number of times I tried. But the setting spray was still a requirement.
Now, make-up aside, lets move to the actual concern -- Skin. Depending on skin-type, you may or may not be able to sleep in your makeup. This has a couple up-sides and down-sides on either end. Upside to sleeping with it on, you have minimal (likely) touch-up the following morning. Probably around your neck, maybe a cheek or forehead. In addition to being able to 'sleep in game'. Downside, the longer you have makeup applied, the worse it'll be for your skin afterwards. For those who can handle it, I still suggest sleeping in your makeup, as a night or two won't cause any sort of lasting issue in the majority of cases. For those who can't, removing makeup (at least the majority) before you sleep is advised, to prevent against rashes, break-outs, and the like. That's also something that no amount of online, experience-derived advice can tell you -- if you can or can't. I suspect that you'll learn through the day how your skin is behaving with a lengthy application of makeup. The big difference that I found between the airbrush and powder, just what they were, is that airbrush makeup is intended to stay on the skin for days at a time, while the theatrical makeup of Ben Nye and Mehron are generally for just that -- a theater performance, maybe two, and don't have as many concerns alleviated in their formulation to allow for extended, embattled use like we'll see over a LARP weekend.
What I can't suggest enough is a proper skin care routine before and after an event -- preparing your skin for long-term makeup application, and then recovering from it. There's plenty of brands out there with different claims, however finding a routine that has no fragrances is critical. These are literally the worst thing for your skin, as they may smell botanical or whatnot, but these are the primary irritants and the biggest difference between "Normal" formulations and "Sensitive" formulations. Outside of that, finding a Face Wash / Cleanser that works for your skin is a minimum. Realistically, you'd want to go into a 4 or 5 step routine to prepare/recover correctly. That's a Cleanser, maybe a toner, an exfoliant for certain, as well as a moisturizer. You might expand to antioxidants, if nothing before that has them, as well.
All of that said (I did say well over two cents), what works person to person is a very mutable and different thing. While people can advise on their experience and what's worked for them, finding a route to what works for your skin and makeup over 48-72 hours is something that you'll know best, though others presenting the road for you can certainly help you find the ideal outcome.
If you have any questions for me specifically, feel free to ask here or in private.