This guide is mostly destined to beginners, as veteran players might not need it much. Yet, it might still be useful to them.
Defensive items










Defensive items, as their name implies, are destined to frontliners. But there are several defensive traits, and as such, there'll be a few discrepancies between the way they use these items.
We've got Bruisers who get bonus max Health, Guardians who grant themselves and their closest ally with a shield scaling on their max Health when they drop below 50% Health, and lastly Sentinels who grant the whole team resistances while getting double that amount themselves.
As such, Warmog's Armor and Redemption are very good items on all of them, but Gargoyle Stoneplate, Bramble Vest and Dragon Claw, while useful, might not be as efficient for Sentinels than the other items. To capitalize on Sentinels' resistances, you'll indeed want to grant them a lot of HP. But they'll do a great job on Bruisers and Guardians, to make their HP, both real and virtual (from their shield) deplete slowly.
We've also got a more peculiar item, which is the Steadfast Heart, an overall very strong defensive item, reducing the damage taken by the holder by 8%, increased to 15% as long as their Health is above 50%. It is extremely efficient on Guardians, along with Warmog's Armor and Gargoyle's Stoneplate. A Redemption on a nearby unit will grant regeneration.
Protector's Vow gives a lot of starting mana, which makes it perfect for a tank whose spell you want early in the fight, such as Thresh. Moreover, when the holder's health drops below 40%, it'll give them a shield amounting to 25% of their maximum Health and give them 35 armor and magic resistance, but only once per combat.
We've then got items that I'll call as supportive (not to confuse with support items), such as Sunfire, Redemption, Evenshroud, Ionic Spark.
Sunfire is a defensive item that you'll want on your frontline, though maybe not on your main tank, as it's used mostly to get anti-heal. You'll want to put it on the same unit that will hold Redemption.
Talking about Redemption, every 5 seconds of combat, the holder and every ally unit within 1 hex will heal for 15% of their missing health while granting them 10% damage reduction (which won't stack). It is very fine on a secondary tank that you can place on the second row to avoid them taking aggro too soon.
Evenshroud will sunder (debuff the enemy units' armor) within 2 hexes around the holder, on top of granting the holder 20 armor and magic resistance for the first 10 seconds of combat. It is a nice item to put on any frontline unit, especially when you need to reduce the enemy units' armor. It will allow you to free an item slot for your carry.
It is debatable whether Ionic Spark can be called a defensive item, as it doesn't give the holder much defense aside from the magic resistance from the Negatron Cloak used to craft it. Still, it is a way to shred (debuff enemy units' magic resistance), but you'll prefer to use a Statikk Shiv on a backline unit.
Lastly, we've got items that I'll call hybrid. Those are Crownguard and Adaptive Helm.
Crownguard is both a defensive and an offensive item. Indeed, it will grant the holder a shield of 30% of their maximum Health for 8 seconds, then, when the shield expires, will give the holder 35 bonus AP. You can stack the Crownguards, though you should keep in mind most of the shield will expire before being completely used and thus go to waste. It will go nicely on units such as Mordekaiser, Neeko, and even Blitzcrank.
Adaptive Helm has two effects, depending on where the holder is placed. On the two front rows, the holder will gain 35 armor and magic resistance as well as 1 bonus mana when being attacked. The item also gives 15 bonus AP on top of the mana and magic resistance from its components, so it is nice on frontliners who need to cast often, such as Amumu.
Offensive-leaning AD items



The two main offensive-leaning AD items are the Infinity Edge and the Deathblade. While both give a nice boost to carry units dealing physical damage (and can be held in combination by most if not all), they don't have the same aim.
Infinity Edge allows the holder to deal critical damage with their spells, while giving him 35% AD and 35% crit chance. Note that if your unit already can crit, if they're an Executioner, if you have a Jeweled Lotus augment or if they already have an Infinity Edge (or Jeweled Gauntlet), it will give them 10% bonus crit damage. Also, crit chance going over 100% will be converted to crit damage with a ratio of 1% crit chance to 0.5% crit damage.
Deathblade is much more simple, as it gives the holder 66% AD, and 8% bonus damage.
While both grant the holder Attack Damage, the Infinity Edge will be better to capitalize on crit chance and on units with a big AD base. As such, you'll want to give one to Samira, Akali, Jinx, Twitch or Caitlyn, for examples. Deathblade shines more when the user attacks quickly, such as Rapidfire units like Aphelios, Lucian, or, again, Jinx and Caitlyn. But it won't be too bad to put them both on carry units in backline.
As for the Runaan's Hurricane, it's probably an item that you won't see much. It grants the holder 20% AD on top of the component's stats, and shoots a bolt dealing 50% of the holder's AD with each auto-hit. If you are to build one, you'll want to put it on a Rapidfire or with a Guinsoo. But there are much better options, so that's really pretty much if you're stuck with one because you've got it as a random item. Note that it doesn't apply eventual on-hit effects.
AP items






People often hesitate between Archangel's Staff, Rabadon's Deathcap and Jeweled Gauntlet. When to choose among them ? To decide, we'll have to consider what they give, and in which situations are our units.
Archangel's Staff stacks AP over time, giving the holder 25% AP every 5 seconds. Rabadon's Deathcap grants the holder 70% AP. Jeweled Gauntlet grants the holder 30% AP and 35% crit chance along with allowing them to deal critical damage with their spells (just like with Infinity Edge, it will give the holder 10% damage if they can already crit with their spells). But there are traits giving the units AP, such as K/DA and Spellweaver. For those, you won't need Rabadon and Archangel, your units will use better the Jeweled Gauntlet (as well as other units that we'll see below). Thus, units such as Karthus, Vex, Ziggs or Twisted Fate will love them.
We've also got mana-generating items, namely the Blue Buff and our acquaintance, the Adaptive Helm.
The Blue Buff has always been a wonderful items for mages with low mana, since it reduces the holder's max mana by 10. But now that it doesn't give them 10 mana upon scoring a takedown within 3 seconds after casting, it's been less used. Still, since it gives the holder 15% bonus damage if the aforementioned conditions are met, it would still be useful on Ahri or Ziggs.
Adaptive Helm, when put on a unit placed in the two rear rows, will grant them 15 bonus AP, and they'll generate 10 mana every 3 seconds. A decent item to put on any AP unit, preferably on those with an even amount of mana.
Lastly, Nashor's tooth will grant the holder 40% Attack Speed for 5 seconds after casting. It is thus perfect for units with mana around 60 (or lower). It is among Annie's best items. It is nice on Twisted Fate when you've got few Disco units, Ziggs, Ahri, Seraphine, Lulu.
Sustain items + defensive options for offensive units







We've already mentionned the Redemption earlier, and thus won't talk about it more here.
Hand of Justice is an item who will grant the holder, on top of the components' stats, 15% AD and 15% AP on the one hand and 15% omnivamp on the other hand. On combat start, one of these effects will be doubled. Thus, it is very useful on units who benefits from both AD and AP, and will be receiving damage. Moreover, as it gives crit chance due to the Glove, it's perfect on Executioners and Infinity Edge/Jeweled Gauntlet users. Think Akali, Kayn, Qiyana, Zed.
Hextech Gunblade and Bloodthirster are iconic sustain items. But the Gunblade is preferred on backline units, as it'll heal the lowest unit (and may save backline units from Karthus, K/DA Akali or Lux). On the other hand, Bloodthirster is better on units who'll go in the melee, such as Viego, Riven, Zed, since it'll give them a shield of 25% of their maximum Health when theirs drop below 40%. It occurs only once per combat and the shields lasts up to 5 seconds.
While the Titan's Resolve, Sterak's Gage and Edge of Night aren't sustain items, it would have been redundant to put them in a separate "Defensive options for offensive units" since I would then need to add Hand of Justice, Bloodthirster and Hextech Gunblade.
Titan's Determination will give the holder 2% AD and 2% AP every time they hit or are hit, up to 25 stacks. When fully stacked, the item also gives them 20 armor and magic resistance. It is then obviously better used by melee units, such as Zed, Akali, Riven, Yone. Since Viego scales poorly on AP, it's not a good option for him.
Edge of Night will shed all of negative effets of the holder as well as give them 15% bonus attack speed when their Health drop below 60%, but only once per combat. Once again, it's good on melee units such as Viego, Zed, Qiyana. While it isn't bad on Akali, her K/DA version loses aggro upon dashing already, so you'll want another item instead.
Sterak's Gage will give the holder 20% bonus Health and 35% bonus AD during the combat if their Health drops below 60%. Don't get your hopes too high, these stats will revert to their normal values after combat. It's best used in combination with Bloodthirster and Warmog's Armor, as the former's shield will scale on max Health, brought to a high value from Warmog and multiplied by the Sterak's Gage.
Sunder and shred items




These four items are meant to debuff the armor (sunder) and magic resistance (shred) of enemy units.
We've talked about Evenshroud and Ionic Spark earlier.
Last Whisper will sunder enemy units hit by the holder's physical damage. You'll thus want it on a unit hitting a group, such as Aphelios, or your main AD carry, such as Jhin, Miss Fortune or Ezreal. Consider using Evenshroud to free a slot on them.
Statikk Shiv will, on every third auto-hit from the holder, shoot a spark which will hit 4 units, dealing little magic damage and shredding them. It's mostly used on secondary AP units, such as Nami, Bard or Lulu. Note that unlike Ionic Spark (except if the holder gets there), it can affect backline units.
All of these debuffs amount to 30%. Also, the flat reduction from Vi, Lucian and Twisted Fate will be calculated before the % reduction, reducing its efficacy (though not rendering it useless).
Offensive buff items




These items are meant to strenghten their holder. They can be wielded by about any offensive unit, though Quicksilver will be favoured for melee units.
Talking about Quicksilver, it protects the holder from crowd controls for the first 14 seconds of combat. During that time, they'll gain 6% attack speed every 2 seconds. Zed, Qiyana, Viego, Riven, Yone will love it.
Giant Slayer will increase the holder's damage by 25% against units that have more than 1600 HP. A must have when the other players line up Bruisers, or have Cybernetic-type augments.
Guardbreaker, as its name implies, increases the holder's damage by 25% for 3 seconds after damaging a shield. Of course, the buff is refreshed upon damaging a shield again.
Guinsoo's Rageblade will give the holder 5% attack speed everytime they shoot an auto-hit. It's mostly used on AD units, but it is still useful on other units, and it's not that rare to see Sona equipped with 3 Guinsoo's Rageblades.
Mana-generating items



We've talked before about the Blue Buff and the Adaptive Helm, but the Shojin's Spear also exists. It'll grant the holder 25% AD and 25% AP, on top of granting them 5 bonus mana per auto-hit. With these stats, it's perfect for both AD and AP units, especially if they need a lot of mana to cast. It's best on units whose mana is a multiple of 15. A unit that won't use it well, though, is Samira, as it'll prevent her from stacking a lot of Style.
Burn + Wound items



These three items are meant to Burn (deal damage over time based on the enemy unit's Health) and Wound (reduce heals by 50%) enemy units.
The Sunfire is meant for melee units, and while the Red Buff and the Morellonomicon apply these debuff on spells, though the former is better on any unit hitting an area (it also gives a lot of attack speed, making it quite good on Aphelios, Senna, Urgot, Twisted Fate, Ziggs) and the latter on AP units, you'll almost never craft a Morellonomicon, as there's currently no really good wielder. Vex, Lux and Twisted Fate want to destroy units, Ahri hits a single target, same for Annie. Karthus and Sona take too long to cast for the Burn and Wound to actually matter. And it'd be a waste of item slot on Ziggs.
Thieves' Gloves and Blacksmith's Gloves

This one needs a dedicated section, as it will give the holder two items that will change at random each round. I recommend putting it on frontline or secondary units, though, unless you've got the Lucky Gloves augment, because it may give your carry units items unfit for them. You don't want a Gargoyle Stoneplate and a Sunfire on your Ahri.