I avoided buying real dining chairs for years, mostly because the ones I liked cost more than the table, which felt backward. We lived with four mismatched chairs from three different houses for most of a decade. What changed was hosting a dinner where someone's chair leg actually gave out mid meal. That settled it.
The gap between a good chair and a bad one shows up in your hands before it shows up anywhere else. Pick one up. A well made wood chair, oak or ash usually, has joints that are doweled or mortised, not just glued and screwed from behind, and the frame doesn't flex when you twist it gently side to side. Cheap ones wobble within a year because the joints were never meant to take the stress of someone leaning back to grab the salt. Upholstered seats are their own test: a solid plywood or hardwood seat base under the foam, not particleboard that goes soft the first time a drink gets spilled near it. The foam itself matters more than people assume, a higher density foam holds its shape through years of actual use instead of going flat and sad after a few dozen Sunday roasts. Run a hand along the welting and seams too. Clean, tight stitching tells you the same hands that cut corners on joints probably cut corners there as well.
Where these chairs earn their place depends a lot on your house and your habits. A small apartment with a drop leaf table wants something light enough to carry one handed and stackable if storage is tight, which points you toward bentwood or simple metal frames rather than heavy carved wood. A family kitchen with kids and regular spills wants a wipeable seat, vinyl or a performance fabric, over anything that needs a coaster for its own existence. A proper dining room, the kind used mostly on weekends and holidays, can afford something more delicate, upholstered in a natural linen or velvet, because it isn't getting hit with syrup six mornings a week.
On color, I've learned to trust the boring choices more than I used to. Natural wood tones, warm oak or walnut, and neutral upholstery in oatmeal, soft gray or a muted clay all sit happily with whatever table you already own and don't date the way a trendy mustard or teal eventually will. The detail that still gets me, years later, is the quiet click of a chair sliding smoothly under the table without catching on the rug, which sounds small until you've lived with the ones that don't.