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The rules on Multiple Similar Magic items are :

Multiple Items of the Same Kind

Use common sense to determine whether more than one kind of a given magic item can be worn. A character can't normally wear more than one pair of footwear, one pair of gloves or gauntlets, one pair of bracers, one suit of armor, one item of headwear, and one cloak. You can make exceptions; a character might be able to wear a circlet under a helmet, for example, or be able to layer two cloaks.

The Slippers of Spider Climb are described as light shoes (which could almost be imagined as socks), so would it be reasonable (under common sense, as above) to allow a character to wear them under bigger boots, like Boots of Speed, for instance ?

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    \$\begingroup\$ I would not agree that "light shoes" are equivalent to socks. \$\endgroup\$
    – V2Blast ♦
    Feb 23, 2018 at 22:14

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It's possible that the boots are roomy enough to accommodate the slippers (especially since they are size magic), but (using common sense) I suspect that the slippers may not function unless they contact the surface to be climbed. They seem to operate by grip given that they don't work on ice, etc.

If not "grip" by ordinary friction, it is by some interaction with the surface they are in contact with, (and they seem to grant the wearer some immunity to the effects of gravity), slippers in contact with the inside of the boots seem unlikely to allow the boots to walk on vertical and overhanging surfaces.

While wearing both reduces the time taken to change from running to climbing mode, it would not eliminate it, nor would it allow running on the ceiling. However it could be argued that the slippers grip the inside of the boots making it hard to remove the boots!

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    \$\begingroup\$ They can't completely work via grip, since gravity is also altered to allow the person to stand erect, sideways. \$\endgroup\$
    – Nacht
    Feb 25, 2018 at 4:25
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    \$\begingroup\$ geckos grip by friction but that may be too much science \$\endgroup\$
    – Jasen
    Feb 25, 2018 at 6:14
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Ask the player to wear a pair of slippers under their boots in real life. If they're able to do this, concede that their character should be able to do it in-game, and that their wacky antics (which will no doubt involve borrowing an exceptionally large pair of boots from someone) have earned them the right.

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Possibly

From the quote it says:

A character can't normally wear more than one pair of footwear

But then it says:

You can make exceptions...

The "you" is the GM and so you have to ask your specific GM on whether he will allow it or not.

I would not allow it since even light shoes would have a thicker sole to protect the wearers feet from sharp stones. Even my slippers at home have a thicker sole that would not allow me to wear boots over them.

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No

From your quote:

A character can't normally wear more than one pair of footwear ...

Slippers and boots are both “footwear”.

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    \$\begingroup\$ The same quote continues: ...one item of headwear, and one cloak. You can make exceptions; a character might be able to wear a circlet under a helmet, for example, or be able to layer two cloaks. - seeming to leave that open to interpretation. \$\endgroup\$
    – Davo
    Feb 23, 2018 at 22:08
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    \$\begingroup\$ @Davo It’s D&D- everything is open to interpretation- this is mine \$\endgroup\$
    – Dale M
    Feb 24, 2018 at 0:22
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    \$\begingroup\$ @DaleM Quoting this the way you did, without even acknowledging the explicit mention of exceptions, is kind of misleading and gives the impression the rules are absolute (when, evidenced a sentence later, they are not). This kind of citation might even be an example of taking the quote out of context. Please take care not to wind up being misleading toward readers. \$\endgroup\$
    – doppelgreener
    Feb 24, 2018 at 9:18
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Yes

'Common sense', in this case, means whatever makes sense to you. People don't ordinarily agree on the truth of 'common sense' cases, they are just likely to act belligerently or incredulously towards those who disagree on the matter. When the rules say you should 'use common sense to...', they mean you should make it up according to what seems right to you, and then treat it like objective fact.

Assuming you are the DM, if you think it's reasonable for a character to wear slippers under other footwear, then that's what's reasonable in your game world. If someone else thinks it should be impossible to wear two foot coverings at once, because 'it's just silly', and they're DMing, then that's what's true in their game world. The rule you quote is designed to explicitly move away from a 'magic item slots' system by explicitly telling you to use your own judgement instead. It gives some sparse few examples of the general outline of reasonability, but is quick to point out that that outline is a starting place, not a rule, by giving the example of cloaks as probably more easily layered than the outline makes them out to be.

By asking this question, it seems pretty clear you already think it's potentially reasonable for someone to wear thin slippers under a pair of larger boots. This isn't accurate to typical footwear in the middle ages, but that's only important inasmuchas you care about such things as a matter of authority on your game world. Ultimately, it's up to you, and the rules seems to indicate the system believes the attunement system has you covered, as far as potential balance issues are concerned.

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    \$\begingroup\$ I'm not sure I understand what evidence that link is suppose to contain. It appears to be talking about sabotons, which are not boots (they are foot-top armour and have no bottoms). They fit over boots/shoes in the same relationship as spats; they're not an example of wearing boots inside other boots. I only skimmed the page looking for the point the link was making—is there something else on the page that was intended? \$\endgroup\$
    – SevenSidedDie
    Feb 23, 2018 at 22:56
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    \$\begingroup\$ Sabotons are different, but there is a possibility there. If the character had Sabotons of Speed, then indeed I would say he could wear both. Standard boots, no, as it looks to me that the Slippers need to be in contact with the surface to work. \$\endgroup\$
    – Phil Boncer
    Feb 23, 2018 at 23:17
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    \$\begingroup\$ @SevenSidedDie No, and I see 5e has replaced the fantasy metal-boot-things for plate armor in their text, though not consistently in their images. Removed. (While in real life sabatons and sollerets with soles were exceedingly rare, there were some (ca 17th c), and I use that term to refer to such fantasy footwear as well) \$\endgroup\$
    – Please stop being evil
    Feb 24, 2018 at 0:19
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is the slippers are as thin a socks then i would say common seance dictates you should be able to wear them under large boots.

Use common sense to determine whether more than one kind of a given magic item can be worn

you can make exceptions; a character might be able to wear a circlet under a helmet, for example, or be able to layer two cloaks.

i think this would be an exception.

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