I would keep the chairs stained if the finish is good. YOu can buy touch up kits. I'm not a big fan of painted furniture unless its really beat up and has little value.

I think the combination of black painted chairs and wooden table can look more modern then if both things are wood. However, I can't really say if you should paint the wood or not. It really depends on how nice the wood and the chairs in general are, because if the quality is really good and you think you might regret it in a few years maybe you shouldn't paint them, but you said you got them for little money on craigslist, so maybe its not so nice and you should just do with it what you want.

A contemporary print cushion for the seat and back of chairs would update it. Take a color from elsewhere in the room for continuity.

Although not the answer you were asking for, another thing that can help a dining table look fresh is how you accessorize it. A really cool vase with flowers, interesting candlesticks, a neat centerpiece...you'll be amazed how quickly that changes up the look.

If this is a vintage piece, or if this is something you think you want to keep for a long time, you probably don't want to paint it. Otherwise, considering you got it for "a steal," it's not like you're squandering away a vast fortune by playing around with it. Remember you can always add a tablecloth or a runner to lighten up the look, as well as some cushions on those chairs.

I have the same issues with painting wood - my kitchen cabinetry had "paint me" written all over it but in the end I painstakingly stripped and re-varnished them all, just because some of the grain was so pretty.

In this case, save the table if the wood is gorgeous and definitely paint the chairs. The chairs make the set look a tad dated, but with crisp black paint they will look more modern.

I think it is actually the design of the chairs, not the wood, that is making them look dated. The matching table is a little bit more understated which is probably why you are preferring it. So with that idea in mind, I think I would try recovering the chairs' seats and then creating a lightly upholstered back that would cover over the wooden cross pieces and create more modern lines for the chairs. 1/8" pieces of wood to create a stiff form (or even decent, hard cardboard), riveted/stapled or bolted together in between the existing braces, covered with thin foam and then the fabric of your choice.

Stain the chairs if the wood is just as nice -- otherwise, go ahead and paint them if you want. If you think there won't be enough of a connection between chairs and table if you leave the table unpainted, just paint the table legs and leave the beautiful wood top as is.

I'd keep them as is..love your new finds!!...How come I never have any luck with craigslist? =p

Painted chairs will nick where they are pushed into the table, I've found from experience. Keep the wood and play with upholstering the chairs (or even just fun and simple slip covers on the backs) to update the set.

I agree with home body. The design of the chairs is what makes them look dated. There's really no way of avoiding that except to paint, and I wouldn't do that unless you were sure you wanted to (though I wouldn't paint them black). If everything is in good condition, I would touch up the wood and reupholster the seats first. See how you like that, then change as necessary.

Paint the chairs white and the table legs white.

If you are determined to paint the chairs and preserve the wood on the table, Id suggest painting the chairs and table base in a modern color like black or even blue (this will keep the table and chairs looking like a matched set), and then choosing a modern print for the chair cushions. You can then leave the table top stained wood and repair if needed and match your table top accessories to the paint color and upholstery fabric you chose.

Make simple white or neutral linen covers for the chairs.

Copy the arch of the back and join two pieces together at just one seam in the shape of the arch. Have one piece that just hangs down at the back, between the side posts. The second hangs in front and they are tied/ velcro-d pinned or something togehter.

You could play with this to see what works best - the pieces could reach the floor behind the chair, or the front one could be long enough to cover the seat and down the front. And new cushions could go under or over the seat.

This way you can decide later about paint vs wood.

I think the combination of the wooden floor and the table and the chairs is what makes it look dated. Maybe if you added a lighter carpet under the table and new cushions for the chairs it would light up the space. If the wood is beautiful and in good condition, you should keep it as it is. :)

If you decide to go for black, maybe consider painting the chairs and the legs/support structure of the table, but leaving the table top bare.

Also, you may want to do a bit of research before changing the chair's seats. Wicker seats are constructed like little hammocks - there isn't any foundational piece to pop off and cover with fabric.

Great set of furniture, I'd love a follow-up to see how it looks when you've updated it!

How about a modern grey and white tablecloth (to help it mix with your sofa)? I also think that a carpet underneath would help.

I wouldn't touch the rush seats, but I would consider painting the wooden part of the chairs and the lower half of the table (everything but the top) in black or white.

Get rid of the chairs and put something simpler with the table... that way it won't look so dated.

It's the height of the chair backs that's bothering me. I would saw off the backs of the chairs at the second cross-piece, then refinish or paint them. Then however you dress up the table will draw the attention, not the oversize chairs.

I love the look of ladder back chairs, but have found they are very uncomfortable. I sold the ladderbacks on craigslist and found more comfortable chairs.

I think the table and chairs are fine, though you might add some seat cushions or upholster then. The colorless back drop is the problem.

I've seen some spectacular results from painting traditional wood furniture black. I can't tell from the pictures but it doesn't appear to be a particularly high value wood species and it's already stained very much darker than its original color so I would go for it.

I like them as is!

jburn, we have ladderback chairs that are very comfortable. It all depends on how they're made.

I'd start with trying a different table cloths and an interesting center piece. And I love your chairs! They have character.

I agree with Homebody. I agree with the fabric choice Dulcibella recommended: pick a linen or linen/cotton blend because linen wears like iron. Linen comes in many different weights; you can find linen that's almost burlap-like, or linen so fine you can see through it (this is called "handkerchief linen".) The lighter weights are softer, but also thinner. This is why you might find a good linen/cotton blend you like, which will be heavy enough to wear well and soft enough to be comfortable.
Also, linen irons beautifully and is great for upholstery/curtain/slipcover projects because it will really hold a pleat or curve well.

One last tip: If you start out with white linen, cotton, or linen/cotton blend, after a while you might want to use RIT color remover to get them back to white, or to dye them. If so, use 100% cotton thread throughout, not polyester, if you think you will ever decide to dye the slipcovers. The linen or linen/cotton will take dye beautifully, but the polyester thread will resist the dye.

I agree with other posters. Get rid of the chairs and paint the legs of the table. If getting rid of the chairs isnt an option then paint those too.

I think the problem you are having is that the space is very, very neutral in tone - wood floor, wood table, no window dressing (that we can see) other than the mini blinds. It definitely needs some color.

I would find some curtains or valances to hang from the windows first, and then find a color from there and paint just the horizontal cross-pieces on the chairs. Any color that fits your decor and would make the dining area "pop" would work wonders. Red, orange, teal, coral, yellow - something bright. I would leave the seats and the table itself alone, but you could also paint the "details" on the table the same color as the chair backs.

Then work on accessorizing the table as another poster said - a vase with some bright flowers, candles, etc.

i much prefer when table and chairs compliment each other rather than match. those chairs will look great painted black, and it will make the whole area look more pulled together.

A steal's only a steal if it doesn't require a Herculean effort to make it what you want. Covering dated chairs with upholstery? Meh. Start with something closer to your endpoint, which saves you hassle AND leaves the original item be, so it can be some older lady's perfect thingy. :)

I agree with toypixie -- the table and chairs are great as they are; what you need is some colorful curtains and some flowers for the table. I honestly think the miniblinds are the biggest thing making the table look dated!

I had a similar situation, except my table is longer, and the chairs shorter in the back. I spray painted the chairs a muted light celery (the color of my walls), and orange. I also gave a finish shiny shellac coat. I think it looks pretty awesome.

Thanks for the great ideas everyone!

i know i'm kind of late to the discussion and i also know i'm a little more obsessed with baby blue/teal than your average person, but i keep coming back to this picture from an old AT house tour: http://gallery.apartmenttherapy.com/photo/sf-kat-house-tour/item/117273

even if you don't paint the chairs teal, i think a bold color with the wood table would look amazing. you could even leave the seats of the chair as-is to tie it all together.

good luck! you should share an after picture... you've gotten some great suggestions so i'm curious to see what you decide to do.