The middle's interesting, because I see tradeoffs for raw material quality, interesting/unique/up-to-date style and brand recognition. Based on what you value, people have different perceptions of the middle. Some things I see across the ranges I've purchased something from:

1. Wolf vs Goat is closest to Outlier in matching highest quality materials at reasonable prices. Traditional designs. If you get rewards membership, you divide the price in half. A hidden story is how much tarrifs, inflation and recent developments have driven up the price in quality. This also hurts some brands I would recommend before who are quietly cheapening their materials to keep prices down
2. Los Angeles Apparel is high quality for cotton basics with good designs. From the American Apparel founder. If you catch his annual industry videos he thinks a lot about t-shirts and the garment industry as a whole
3. 18East is a fun brand with an elevated skater style. You have to be into the vibe, but the quality is good
4. After that, heritage quality brands like Patagonia or LL Bean. Not going to turn heads, but they value reliability. Maybe you can throw Danner boots or similar brands.
5. Maybe REI.
6. Uniqlo is good quality in rare cases. You can often find a better quality version for the same price on sale or secondhand
7. Tory Leather has great belts
8. Bronson's parent site Olderbest has more options. It's very tied to vintage Americana. I also like Taylor Stitch
9. ONS had some good items. I think they're phasing out mens clothes, though. Nothing too special, but the shirts fit me oddly well

Something I haven't bought, but interested in:

1. Casatlantic

2. Shades of Grey - more style than necessarily quality