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My house has serviceable but plain-looking windows:

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I'd like to spruce them up a bit, by installing some exterior trim that can be painted in a contrasting color when we have the house painted in a month or two. I like the look of something like

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or

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My questions are as follows:

The windows in the examples I gave seem to be inset from the wall, whereas mine comes out from the wall. What's a good way of dealing with that without it looking terrible? Do I need to cut some kind of angle into my trim boards to cover that up?

The angled part also has weep holes. Does that mean I simply can't cover up that part, or can I cut corresponding weep holes into my trim?

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The problem that you will have is that you have stucco walls, this complicates the attachment of any decorative trim (but does not make it impossible).

For your application I would suggest lightweight foam architectural trim, painted as you wish. This is commonly used around windows on homes with stucco walls (albeit it is usually installed on the "brown coat" then stucco'ed over). The advantages are that it can be attached using special adhesive, you then caulk around it and paint; any other type of trim (wood, shutters, etc.) would require drilling into the stucco and using anchors to fasten.

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  • I don't mind drilling into the stucco (in fact I did it to install trim around my door). The bigger issue is making the stucco work with the existing window frame and the fact that part of the window is convex.
    – Catherine
    Commented Jul 14, 2017 at 21:39
  • I don't see why the convex frame is an issue. Your trim should not cover the existing frame, it should lay right up to it. The weep holes should remain clear that way too. If you don't mind drilling and using screws (and maybe anchors) then you can use any trim you want. Commented Jul 15, 2017 at 0:33
  • I just worry it will look weird to have a frame of a different color around a (already quite wide!) frame that's white.
    – Catherine
    Commented Jul 15, 2017 at 0:38
  • I see... it's kinda hard to visualize the "convexity" of your frame when looking at your pic. Hmm...you can paint the vinyl frame if you use a special primer? Commented Jul 15, 2017 at 3:06

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