Since there are so many held items to choose from, it's extremely important to know which items every trainer should start with. For example, Leftovers was one of the very first held items introduced that played a significant role in battle. Having a passive recovery (1/16th or ~6%) of your maximum HP every round is extremely important for the longevity of bulkier Pokemon, or walls as mentioned before. Many bulky Pokemon do not have access to recovery type moves making this item all the more useful. Black Sludge works in a similar fashion when equipped to a Poison type, and works in the opposite manner(-6%HP/round) when equipped to anything else. This makes Trick/Switcheroo users wary of poison types as they generally do not care for residual damage. Another great item for beginners works in almost an opposite manner, but is just as important. The Life Orb actually inflicts 10% (Max HP) damage every time you successfully land an attack. Now you might be asking, why is this useful? It also gives a flat 30% power bonus to any move used by the holder. This is one of the signature sweeper items as it generally gives attacks just enough extra 'oomph' to turn a two or three hit KO into a one or two hit KO. It can also be very handy for Pokemon who take advantage of having lower HP with moves like Pain Split. A similar item known as Expert Belt gives a 20% damage boost without the recoil damage, but it must be a super effective hit, whereas Life orb's bonus is constant.
Some held items are consumable, meaning that they have only one use per battle. A prime example of an item of this type are Berries. Some berries instantly restore a percentage of HP while others reduce damage from super effective hits. There are literally dozens of useful berries for competitive use, but there are a couple that stand out the most. Chesto Berry was one of the first items to allow players to utilize the move Rest with little consequence, as it wakes up the holder upon falling asleep. The Resto/Chesto combination was popularized by bulky set-up sweepers such as Snorlax with the move curse, allowing the bearlike creature to take a short nap and continue to set up two, three, possibly even five or six Curses almost entirely securing a victory. Lum Berries cure any form of status ailment upon infliction. This is particularly useful for sweepers who would be completely neutered if they were Burned or Paralyzed.
Have a fragile Pokemon who needs more longevity? Focus Sash is a one-time use item which when consumed, leaves your Pokemon at 1 HP when hit by a move that would knock it out. The ability known as 'Sturdy' works in a very similar way. Keep in mind that the sash/sturdy ability can only activate when you're currently at full HP. This guarantees one free turn for the Pokemon to either set up a boosting move, put something to sleep, or just ensure you can survive a hit and retaliate. It is also important to note that entry hazards such as Stealth Rocks will essentially break the Focus Sash, so having Rapid Spin/Defog support is often necessary.
Air Balloons are also consumable, and are exceptionally useful for any and all of the Pokemon weak to Ground type moves, as it grants immunity to ground type moves until it's 'popped' by another type of move. Earthquake is one of the best staple offensive moves in the game, so having an immunity (outside of Flying types) is quite useful.
Among the new items to enter the fray, Weakness Policy might be the most game changing. It allows for Pokemon to get a 'free' boost (+2 to both attack and special attack, equivalent to a x2 power increase) when hit by a super effective move. This may not seem that great at first, because who actually wants to take a super effective hit? There are quite a few bulky sweepers, generally who also have access to priority moves, who can take advantage of this quite well. Dragonite (with Multiscale) and Aegislash are the primary users because they both have substantial bulk and access to strong priority moves(the moves that 'always' go first), so they worry less about being revenge-KO'ed. It is also possibly for less bulky Pokemon to take advantage of this item if they have the move Endure(to survive the super effective hit) and have a substantial amount of speed. Once again, priority moves like Sucker Punch or Extremespeed are key.
The other new item worth mentioning is the Assault Vest. While it restricts the move choice to only attacking moves, it grants a (massive)50% bonus to Special Defense! This combined with high natural bulk and/or attacking moves such as Giga Drain or Drain Punch can spell doom for opposing special sweepers as they'll be hard pressed to do almost any damage while likely being forced out or KO'ed in return.
Lastly, but perhaps most importantly, the 'Choice Items'. There are three held items known as Choice Band, Choice Specs, and Choice Scarf which every trainer will encounter eventually, likely many times. Equipping any of these items restricts the Pokemon's move choice to the first move selected, however switching out and back in will grant you a choice of all your moves again, until you select a move. Also known as "Locking" your moves in, it greatly reduces a Pokemon's coverage. That said, it is still important for holders of such items to have good coverage, because there's no point in locking yourself into a boosting move and little point to locking yourself into a status move (although some advanced strategies utilize this as a "surprise" factor). These items take the most amount of prediction to use correctly, and are often best used toward the end of a match, however they do serve slightly different roles.
Choice Band/Specs increase the holders Attack/Special attack by 50% respectively. Generally speaking, holders of these items are referred to as "Wallbreakers" because the extra damage output allows for 1-2 hit KOs on even some of the bulkiest, most defensive Pokemon. The 'trick' of the matter is making sure the right move hits the right target. A resisted hit from a 'choiced' Pokemon will likely force a switch of the user, losing precious momentum. Some banded/specs Pokemon can actually work very well as sweepers too, although they almost always have exceptionally high speed or access to a powerful priority attack like Bullet Punch, or both.Choice Scarf is its own entity entirely. Granting a bonus of 50% to a Pokemon's speed can be completely game changing, allowing slower Pokemon to surprise and out-speed their generally faster opponents, helping it to eliminate faster threats while clearing the way for its fellow sweeper(s). Equipping a Choice Scarf to an already fast Pokemon grants it almost uncontested late game sweeping potential. Experienced Trainers will generally try to bluff/disguise a Pokemon as un-scarfed, while bluffing a non-scarfer as scarfed can prove equally valuable. Once the opposing threats/walls are out of the way, it's smooth sailing for a speedy sweeper who cannot be out-sped by anything but another scarfed Pokemon.
As with move sets, item usage is also a matter of prediction. Predicting correctly can only come with experience but knowing what each item does and how it may influence a battle are the first rungs on the ladder to victory. Many Pokemon can take advantage of several of the aforementioned items, so it's important to analyze current popular trends, and to experience many battles to try and stay one step ahead of the competition.

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