Maybe an unchained rogue and magus?
Sorcerer/magus/eldritch knight are all very far removed from what Jarlaxle is, in flavor and functionality.
He's obviously "rogue-ey", loaded with charisma, and has bags and bags of tricks. It would be difficult to create anything resembling him without being high enough level to justify having tons of gold worth of magic items.
I'm assuming you suggested the sorcerer/magus/eldritch knight route to account for his magical tricks, but that veers too far off course of emulating Jarlaxle, in my opinion. At that point you may as well just abandon the exercise.
To make Jarlaxle you need:
According to the wiki, he was just a high level Fighter in both 2e and 3e. I don't know why everyone assumes he was a Rogue, but then I've never been into the whole Drizzt thing. Apparently he was a fast talker and very knowledgeable.
You might have to accept that he was a high level Fighter with really good rolls for stats.
Swashbuckler, get a trait that makes UMD a class skill, and I'd take Skill Focus (UMD).
I'd also consider Skill Focus (Diplomacy) but would prioritize it low. Half Elf gets you the feat for free, so that's an option.
Let me know how this goes, I'm interested in hearing how he turns out.
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He is specifically noted to be using a "swashbuckling" style, that Entreri initially regards as flamboyant and useless, and eventually as flamboyant and dangerous.
I would say swashbuckler/rogue.
I think the real key for playing any of the cast of the 3e Greenwood/Salvatore characters is just being a way higher level than most of the rest of the world. Most of the core cast is well above those around them, and will be very hard to imitate at lower levels.
Perfect class, the Occultist.
Very large number of spells known for a 6th caster and lot's of little trinkets to mimic magic items. Can be built to be a good fighter.
For Jarlaxle himself it would be Swashbuckler, that trait lizard mage describes, leadership and lots of gold to you can be decked out like Mr T.
I don't know why everyone assumes he was a Rogue, but then I've never been into the whole Drizzt thing...
It's because he leads a literal band of rogues, is sneaky and skilled, acts in scandalous and underhanded ways, and uses rogue-oriented weapons. Yes, a fighter could certainly pull these things off, but his character seems more akin to a rogue at a glance, I suppose?
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If I might add, those of us who enjoy RA Salvatore's novels aren't necessarily "into the whole Drizzt thing." The stories are awesome and with characters like Jarlaxle, there are many more things to love than Drizzt.
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Perfect class, the Occultist.
Very large number of spells known for a 6th caster and lot's of little trinkets to mimic magic items. Can be built to be a good fighter.
For Jarlaxle himself it would be Swashbuckler, that trait lizard mage describes, leadership and lots of gold to you can be decked out like Mr T.
Yeah. This. Occultist is the class to mimic having magic items without actually spending huge amounts of gold on magic items.
"Highly effective" is subjective. I am assuming you want items that handle a variety of situations, but are not expensive. I would look into the token such as the one that changes into a boat. Jarlaxle was a high level character with a lot of magic items, and good connections. Until you get to a certain level it will be hard to duplicate him. Going outside of the rules is a better option if you are the GM.
I recommend a large number of consumables. Single use items and partially charged wands are a great way to be prepared for everything while not blowing wealth out of the water.
My vote is for the swashbuckler; high int, char, and dex. Just uses the magic items others have made. Trait for UMD.
Commoner!
Alright, seriously I'd go Swashbuckler/rouge (worked awesome before), and maybe a lvl of sorcerer so alot of his magic "items" can be him casting a bunch of low lvl utility spells (truestrike, feather fall, ect). Good luck and still keeping my ear to the ground!
First off, list what you want from him. Common items had were bracers that created daggers to throw, or that could elongate into swords. Serpent belt. Portable holes as buttons on a jacket. Eye patch that allowed blocking of mind reading. Feather token that created a bird combat ally. A nightmare figurine of wondrous power. Boots that made him loud or silent. futher items depending on situations.
Swashbuckling fighting style with two equal length swords. plans, plots and cunning. Definitely charismatic leadership.
Your looking at an unchained rogue, with the swashbuckling archetype most likely. Maybe rake for the bluff. Two weapon fighting feat chain. And maybe investigator for extracts to cover assorted magic items, and his cunning in battle from studied combat.