Not a dumb question at all and you'll probably get differening opinions on this. I have a friend that has white woodwork throughout her house except in her living room. She did white shutters, even where the the wood is stained. I don't think it looks that great though. I would go with a stained wood shutter. I think the white ones look good when they look like part of the window and trim. You can't tell where the window trim ends and the shutter begins. I'd try to get that same look with matching stained shutters if I were you.

I would stick with the stained shutters. I don't think white would at all cheapen the look of your house from the outside; but I wouldn't mix the white with your stained oak inside anyway. I'm guessing that custom stained plantation shutters will be pricey, indeed. Even if you had to skimp somewhere else, I would stay with the stained.
Love to see them when they're finished.

I think white would look funny with stained trim throughout. I would stick with the stained kind. Shop around. I was going the HD/Lowes route when by chance my coworker recommended a private window treatment shop. Turned out each of my french doors ended up being $200 less for EACH door panel. That saved me $1200 as I have 3 sets of doors. Plus I got waaaaaaaaaaaaaaay more personal service from him. Shop around.

Great question, actually, and one I asked here myself not long ago. I think the shutters will look better if they match your woodwoork. We're going with Shutter Classic for our shutters. They will custom paint their basswood shutters free of charge, and they will also custom match stain colors for a one-time $125 charge, no matter how many sets of shutters you order. I am posting details below from their site. Our shutters will be custom painted to match the trim in our home. Shutter Classic has been extremely easy to work with so far, although the shutters are still on order and won't arrive for another few weeks or so. They also have some standard stain colors you could check out (and order samples) to see if any match your woodwork. Here is some quoted information from the Shutter Classic web site for their basswood shutters:

Custom Stains -
You provide us with a physical sample of the stained wood that you want to match.
We then do a custom stain match and ship samples of our custom stain match to you for approval. If the stain needs adjusting, we take another pass at it until we get it right.
Once we receive your approval, we stain your shutters with the custom formula.
There is a $125 one-time flat surcharge for this service for our Basswood shutters. No matter if you order one shutter or an entire houseful, the surcharge is only $125.
Include your name and mail your sample to:
Attn: Custom Color

Shutter Classic

1408 N. Fillmore St. Suite 16

Arlington, VA 22201

Click Here for details on custom paint colors and stains for Crestview, Classic Line, and Alder Plantation Shutters.

A few words about wood shutters: Due to the fact that wood is a natural product, wood grains and color tones vary. This is what makes wood stains so beautiful. Stained shutters will have similar variations in color tone and grain pattern - which of course is why people love stained wood. Your shutters may also have these variations from the samples you receive.

Here is a link that might be useful: Shutter Classic Web Site

Jan in Wisconsin: That looks like a great option for shutters. I wish the internet had been so expansive when we were looking for plantation shutters. They were so expensive locally, that I could only afford to put them in my dining room and did other things in the other rooms.

wildlifelphotomom: You might even be able to get them unfinished and match the stain to your other trim once they're shipped to your home.
That's why I love this forum -- there's a wealth of information out there.

Annie1971: You're right that you can get the shutters unfinished too. That's another option offered by Shutter Classic. I was even able to get the oil-rubbed bronze finish for the hinges that I wanted. I am getting cafe style shutters for two bathrooms. The total I'm paying, including custom paint matching and shipping is only $250.00 total for both windows. I think that's a pretty good price. I sure hope they are of great quality and easy to install.

A HUGE thank you to all who helped me answer this question. In my mind I thought I needed to stick with the stained plantation shutters (but my decorating sense is NOT what some of you have out there) ;-)I surely vallue all of your input on this and thank you for the info.

You can get by with white shutters on the inside even though you have stained trim, however, why not stain the shutters the same color as the trim?

There are companies that will stain/paint match for you.

You may want to check out Horizon Shutters to get an idea of how much the shutters would cost if you were to have them stain matched.

Or, if you want to stain or paint them yourself you could check out ShutterLand and buy stock size, unfinished panels. That'll save you a nice chunk finishing them yourself.