After initially jumping into the wealth of knowledge on eye makeup techniques, I pulled back and started looking for information about pale skin tones - and specifically those with freckles. I found the result strangely lacking. I suppose it should not come as a surprise, growing up I rarely saw others with freckles - and certainly not in the movies or TV (unless it's a bully!). It does appear more acceptable now to let your freckles show, but I still find it surprising how many ladies cover them completely.
I always viewed my freckles as a good thing, they were unique and fun. However I did really think that I couldn't wear face makeup, that they just didn't make it light enough for me (in the drugstore brands, I never thought before I would want to spend the money for high end). When I was young, my mom was trying to give a little guidance; her skintone is much darker than mine, I had gotten my dad's complexion. We concluded that there just wasn't anything that would work for me outside of translucent powder. Things sure have changed in the past 15-20 years.
I have read articles here and there that instruct you to match your freckles instead of the skin underneath for foundation. Unless taking the makeup down my neck and chest, I just can't understand how that works! I have used tinted moisturizers that were a tad too dark (before returning them). My face is darker than my neck by a fair amount, and I have many more freckles on it than my neck. If I go nearer to the shade of my freckles, the line around my jaw is quite startling.
Granted I have full-face freckles, not just a smattering across my cheeks. They have faded over the years, and now in the winter up north, I struggle to see some patches. But I do look forward to summer and they will again perk up a bit.
Working with a shade similar to my neck (or a little darker), may initially look light but it seems to give the best effect. I do feel I can only apply at most medium coverage, otherwise I strangle my poor freckles out of existence.
Another lesson learned was that my skintone works best with warm colors. Finding lipsticks that didn't go immediately super dark on my decently pigmented lips against pale face, that didn't clash with my skin, or make me look half dead (lighter cool colors are the culprit there!) -- that I find to still be a struggle. But ever persistent, I keep buying new things. It's a tough life! If I have one suggestion for someone having similar troubles, it would be to get color matching and application by a professional a few times. It can be an expensive and time consuming process of trial and error otherwise.