Hide at plain sigh

[Aleister VII]

Hey everyone I'm thinking in creating a rouge for the first time I'm I've a roleplaying concept that I want to try.

Basically a rouge that hide at plain sigh, she's always going stealth and surprise everyone apparently appearing out of nowhere with a monotone expression making crude comments or pointing out the obvious or putting a dagger in the throat of whoever the party is trying to intimidate.

So... how I mechanically do that? I'm considering hide in elements from a wood elf but that obviously won't work in towns, cities or dungeons, there's also the skulker feat that allows you to hide in dim light... so that's mean that I can possibly hide in every shadow or obscured place?

[Kane0]

Halflings can hide behind other people, that sounds like a good place to start.

Not sure we can do much about that makeup though.

[hymer]

Not sure we can do much about that makeup though.
Get some crushed, dried berries of a red variety, and mix them into your basic skin gel, et voilà!

Other than that, lightfoot halfling is definitely the way to go to maximize your chances for stealthing. Picking up Skulker may help if your DM starts having the monsters go around your allies to find you.

[Unoriginal]

You literally cannot Hide in plain sight.

There are some methods to hide in more areas, like the Skulker feat and being an halfling or a Wood Elf, as was mentioned, but none of those things make you use stealth in plain sight.

[Tanarii]

Ring of Invisibility would do it.

Other than that, you're limited to ways to make hiding while not in plain sight more easily possible. Skulker is a really good start.

Edit: by the way, the 5e designers intentionally went out of their way to avoid concepts like "going stealth" or "stealth mode".

[Armored Walrus]

Not sure we can do much about that makeup though.

Considering English appears to be OP's second language, this may be a bit too subtle. OP - The word for a scoundrel, ne'er do well, or shady character - and for the Class in D&D - is "Rogue." Rouge is makeup that women (well, these days not just women I guess) put on their cheeks to make it look like they are a blushing youngster.

Might as well also point out that you hide in plain "sight." A "sigh" is something different.

English lessons aside, I agree that Lightfoot Halfling with the Skulker feat is probably the best way to accomplish what you are looking for. If you really want to get crazy, see if your DM will allow you to homebrew a "half halfing half wood elf" race that gets both stealth options. ;)

Edit: I second the Ring of Invisibility. If you're playing in a campaign where the DM takes into account what kind of magic items the party wants when doling out treasure, you should vote for that Ring.

[Specter]

The public version of stealth is disguise. Be a Bard or Arcane Trickster with the Actor feat and Disguise Self, that way you can be whoever you want.

[Aleister VII]

Considering English appears to be OP's second language, this may be a bit too subtle. OP - The word for a scoundrel, ne'er do well, or shady character - and for the Class in D&D - is "Rogue." Rouge is makeup that women (well, these days not just women I guess) put on their cheeks to make it look like they are a blushing youngster.

Might as well also point out that you hide in plain "sight." A "sigh" is something different.

English lessons aside, I agree that Lightfoot Halfling with the Skulker feat is probably the best way to accomplish what you are looking for. If you really want to get crazy, see if your DM will allow you to homebrew a "half halfing half wood elf" race that gets both stealth options. ;)

Edit: I second the Ring of Invisibility. If you're playing in a campaign where the DM takes into account what kind of magic items the party wants when doling out treasure, you should vote for that Ring.

Looks like my phone keyboard messed up with "rogue" but you got me with "sight" x.x I always confuse those two words...

Anyways looks like skulking behind my party is the best way using a Halfling, I don't like them too much as a race but maybe I can refluff them or something, maybe even homebrew the "Wood quarterling" to hide behind my people, hide in the nature and take skulker to be hide as much as I want xD

And despite the invisibility ring being awesome is very unlikely that I can get one and I don't like to rely on magic items as it's very DM dependant or sometimes random, the exception are +1 or more weapons but getting at least one of these is a must unless your DM hates you x.x

[Armored Walrus]

If you have a reasonable DM you should be able to work with them to homebrew a "Wood Quarterling" I would think. There are rules for it (homebrewing races) right in the DMG, iirc. You'll probably end up giving up the extra movement and darkvision, I'd think.

[apepi]

There is already a Hide in Plain Sigh ability and it is a Ranger one.