If dark chocolate brown makes a comeback I may have to find an excuse to add to my F/W closet! I've also seen some dusty blues - wonder if those are going to be trending as well?

Re: lipstick, Id suggest checking Etsy. Many, if not all, the shops selling cosmetics on there offer samples, about 20 cents each usd. So you can try on a bunch of colors that may look similar in photos but be quite different irl.

Also, I tend to find that Everlane's color choices are on the mark. Their latest batch of t-shirts include olive, rust, a dark orange they call topaz (my birth stone and hair color all in one!), and a muted blue that I'd call cornflower. And what they call pale lavender but I think is more like lilac, which might be the new millennial pink? Aside from the lilac, it's definitely a shift towards fall/earth tones.
https://www.everlane.com/collections/womens-tees

I have definitely noticed the resurgence of brown shades, and I'm pretty excited about it A couple years ago I would've sworn up and down I wouldn't be adding any more brown to my closet. I think I've reached a saturation point with black, that is, every category in my wardrobe has at least one black item: jeans, pants, coat, jacket, shoes, boots, sandals, tank top, tee, dress, skirt, hoodie, blazer... Having that black base means incorporating some lighter browns should be pretty easy. These are the items I've had on my mind. I will probably do a small dusty blue/toffee capsule (for once my own tastes are aligning with Angie's forecast!) to pair with black but also with white and navy. I also plan to continue riding the burgundy/blush train for a while longer, as I'm always drawn to a red-based palette for it's energy and warmth once the weather turns cool. I also won't say no to more navy/mustard pairings, a la the Wren dress -- perennial favourite for me, especially with a little white thrown in. Mustard/dusty blue/white is sounding good too.

The lipstick question is interesting. I find bright red lips looking a little bit too harsh/stark these days, but maybe try a sheer red gloss, or a more muted brick red? I'd never heard of matching lippie to outfit colours! I'm much more concerned with finding shades that just look not-awful.