Filling gap between floor tiles and skirting

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Dear Experts,

I'm repainting my kitchen. The skirting boards seemed to have about six layers of paint and looked awful, so I decided to strip them back to the wood; this has taken a while but I think it will be worth it.

The floor has ceramic tiles which were obviously fitted after the skirting i.e. the tiles abut the skirting, rather than going under it. There is a rather ragged gap which had contained various sorts of filler and also looked a mess; I have pulled all of that out.

Now I'm unsure what I should do with this gap. Options include:

1. Fill with a paintable filler ("decorators' caulk"?) first and paint the same as the skirting.

2. Paint the skirting first, then fill the gap with a non-paintable (silicone) filler.

3. Fill with tile grout (???).

4. Hide it with a quadrant bead.

What do you suggest?
 
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You don't want to be putting caulk on the floor and painting it because it will get grubby in no time and with regular mopping/washing of the tiles it will quickly fail. The same tends to happen with most silicones too.

Grout is the neatest and better option, but if the gaps around the edges are pretty uneven, covering it all with a quadrant bead sounds like your best bet to me.
 
I'm unclear where the gaps are. If they're between the end of the tiles and the face of the skirting then match them with the floor (using grout maybe?). Similarly if they're under the skirting but above the face of the tiles they'd look better done to match the skirting (maybe filled and painted?).
 
The gaps are between the ends of the tiles and the face of the skirting.

I think i have some left-over grout somewhere so I will try that out and see what I think of it. Of course the existing grout between the tiles is old and grey, so new grout will contrast....
 
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I would paint the skirting then apply a White silicon bead between the gap of the floor tiles and skirting, unlikey to fade or get grubby plus it is waterproof when cleaning the floor.
 

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