Yes, I agree. What do you think about the sides?

Sides are normally just a caulk joint. If you are feeling very industrious, you could rip the trim in a manner to close the gap slightly, but it would be a caulk joint.

The other option here is the cut the siding back in these locations and apply the trim straight to the sheathing wall (if there is any).

How about some pictures and more details about if there is any sheathing and what the rest of the make up is. You are adding a big "speed bump" to a wall that hasn't leaked before and may be introducing some issues in a very wet climate.

Sample front window, with siding. Back window, with T-111 gen 2.

Windows on WA, thanks for your thoughts. I haven’t pulled up any wood to see the flashing (or lack of flashing), so I can’t give you more details other than what the pictures above show. You’re right that I may open a can of worms for a cosmetic improvement!

you could just butt it up to what looks like a J -channel built in to the window. I think you would be safe to do it without any caulking or head flashing. Putting in a head flashing would not really be that beneficial in this case and can be a real pain to get in correctly.

Thank you for your advice, everyone. @toddinmn, it’s very tempting. Now that I am looking at other people’s window frames, I have window frame envy!

The pic you showed is a pretty simple design. You could Could pre assemble 1 and just hang it there like a picture to see if like it.

The home we bought a couple years ago is the same. It just looks so unfinished. I have been thinking of doing the same

There is also azek board for trim which is an weatherproof composite which can be cut to size and come is various widths x 8' x .75 inches thick and is less expensive than PVC sold at Home Depot. There is an online company "Architectural Depot.com" which I used to order colonial style brick mold for my front door. Their website is user friendly and interactive in that you pick your style and size you need and the calculator give you the exact price. The order form is online as well. The offer brick mold in wood and polyurethane.

@nanitamalia coming in here years late because I have the same issue - what did you end up deciding? I'd be greatful for any info!

Yes we recently moved & have the same dilema. What did you end up doing to widen your trim?

Hi all, I just came back to this post and all of your thoughtful replies. Thank you. I admit, I got sidetracked and have not done anything about this. My handyman at the time, a very experienced carpenter, advised me not to put a frame on top of the siding, but cut away the siding to add a frame. It sounded too daunting and expensive to me, so I opted not to get into it.

I had the same dilemma when updating our exterior trim — it's surprising how much of a difference those details make to the overall look of the house. I ended up going with a simpler, cleaner trim style because I wanted the windows to stand out but still feel cohesive with the rest of the siding.

One thing that helped me was looking at lots of photos of homes similar to mine to see what felt right. Sometimes seeing it in context makes decisions easier than just looking at samples up close.