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i've been using high-gloss paint that doesn't require primer for mine.

after getting *drips* on sections, i've learned to go slow with the least amount of paint possible on my brush! otherwise, i've been going back and sanding off the drips and touching up with a tiny brush.

make sure you let paint like that dry about 4 or 5 hours before touching it - fingerprints show up!

:-)

I've painted furniture but only after I've made it :). I'd rough them up first and do a test on a small section on the bottom (you can always sand this back off). Try all chairs individually because they may have different finishes on them. Make sure there are no rough spots or lines from something that go spilled on them as tiny lines and un-smooth finishes will stand out when you put the paint on.

I just did this to a pair of old (actual wood but not worth much) chairs that I inherited. I used a little sandpaper to rough up the wood a bit, but certainly didn't strip the chairs. Then I used spray paint. I have a few drips that I could have avoided if I had taken more time (I'm really impatient), but otherwise I'm really happy with the outcome.

Great and relatively easy project:
1. Remove seats
2. Try liquid de-glosser rubbed on with a cloth to take off any shine so paint will stick
3. Spray carefully with a primer, let dry
4. Spray carefully the paint color, coat again, let dry for a few days
5. Reupholster seats following the many reupholstery tutorials on Apartment Therapy such as:
http://www.apartmenttherapy.com/chicago/how-to/how-to-the-lazy-upholsterers-midc-dining-chair-redo-070314

Enjoy the new chairs.

When you are painting things like the chairs with cane backs (or even grates or shutters) paint the front side first, in small portions, and periodically turn it around to mop up the paint that dripped through to the back. This will keep the drips from hardening and usually enough paint drips through that you don't have to re-coat your brush to do the back. You will inevitably push some paint back to the front, so when you reverse sides again, be sure to spread out those final drips with your brush. But this front-back-front method has proven quite effective for me, even if time consuming. I also find the end result is usually better than using spray paint, because the spray also causes drips but you can't catch them in time before they've dried a little, and then you can always see the outline.

Do you have a lazy susan? if you have a largish one (~14"), lay a piece of plywood on it to create a turning workspace. Put it, along with the chair on a low table (coffee-table hight). This will help make the process easier on your muscles, and you'll be less likely to rush through some of the tedious parts of the job.

My friend and I recently updated her dining set with 4 different chairs, much like you have here. My tips: Sand the chairs like there is no tomorrow before doing anything! The stain and varnish that are on these chairs will not allow paint to be put on very easily! Also, apply the first coat of paint with a brush, and let dry. Use a roller or sponge brush (for smaller spaces) for the second coat.
Enjoy your project:
http://nate-and-megs.blogspot.com/2009/05/annies-dining-chairs.html

Topcoat, topcoat, topcoat. After whatever paintjob you do is totally dry and cured (which usually takes a few days), spray those puppies down with at least 3 light coats of satin polyurethane. It will make them easier to clean and prevent chipping. Dining chairs tend to get dinged and scratched a lot and a banged up paint finish can quickly undo all the hard work you've put in to improve the look of the chairs.

I agree with the sanding, cleaning and a primer. They will look good initially when skipping these steps, but will easily peel later. You may even want to put a varnish or something similar over the final color coat.

I've done so many chairs through the years and have always regretted when I skipped steps to save time and money.

I've always used the Orange gel stripper. I know a lot of people don't strip the stain, but I'm a perfectionist and this way I know - no matter what - the new paint will stick. I just did four dining room chairs and a table myself - and after a lot of stripping and sanding used a primer and satin finish paint. They look great and I'm so proud of them every time someone comes over to share a meal with me!

For that particular bouquet of chairs, I think it's important to remember that it can be tricky painting that wicker stuff.

If you're planning on painting them with a regular brush, I would consider getting some Rust-o-leum, because they make the same versions of their paints in spray paints as they do in cans.

I would seriously consider spray-painting the wicker parts, and if so... MANY coats that are VERY light, and give several minutes for them to dry between each coat.

And THEN, I think I would brush on the can version of the color onto the main wood parts of the chairs.

But to answer your question about priming -- I do think that the wood part should be at least roughed up a bit. There's a product called something like Liquid Sandpaper or something like that and it does that without doing much extra damage.

But I don't think you should use that on the wicker part, and do be careful with that part, because if you "soak" that, the reeds or whatever will probably either sag when wet, and/or tighten up and break once dry. That's why I'm talking about lots of very thin coats. Oh! AND... you don't want it making little bubbles inside the holes of the wicker stuff.

Sand! Prime! Sand!

Then paint away. It seriously make a difference.