Suggest you consider chair weight when moving in and out from the table, whether you want a low back or high back, and whether you want all hard surface vs upholstery.

At our local artsy decor venue yesterday I saw bow back Windsor chairs sprayed a flat black.. They looked really good. Might be something you could find on CL at a good price and spray yourself.

I like the Pier one ladderbacks but you'd best check the seat height in relation to your table. If it were me, I's spray paint the table black too and distress it a bit. Wow would your Fiesta ware pop and it would present a more cohesive look.

Interesting about spray painting it black! That intrigues me, since it would make it look a bit more modern...actually, way more modern. Is there a rule of thumb about how high chairs should be in relation to the table?

I think I would paint the base of the table, rather than the top, as it would help break up that sea of oak where the table meets the flooring.

Honestly, if the chairs you have are comfy, I would paint them in a color that matches your Fiestaware.

Here is a link that might be useful: painted chairs

Hello! I actually just registered on the site to answer this, because it's funny you should mention the Pottery Barn Isabella chairs. I think those would be great, but here's where you can get 2 for less than the price of 1 from Overstock:

Here is a link that might be useful: Paloma Dining Chairs

Your table has a lot of visual weight. You need chairs that have a heftier look than the ones you've selected. They are lovely, but too delicate for the table. Something like the one in the right foreground in the photograph of your dining room -- do you have more of those? I like the suggestion of painting the chairs -- either black or one of the colors of your fiesta ware.

I would suggest fully upholstered chairs, except with the children that might not be a great idea!

I see that one of your kids is still in high chair mode.
I have a round table, similar to yours, but mine is a real 1900 antique. I have had it since I had a highchair sitter and a toddler. I also didn't like the sea of oak, so I painted the pedestal of the table ( and have regretted that almost daily since about 3 years after I did it!) and painted the oak chairs that went with the table.
Well, the chairs soon looked awful from kids pushing them into the table and chipping the paint and generally "using" the chairs.

My advice would be to get tie on chair cushions to break up all the "oakey-oak" and when the kids have a few more years on them, then find new chairs or paint the old ones.
I now have black Hitchcock chairs with my table....and they are now looking like they need some help!

I like the look of this set. oak table and black chairs.