I'll be honest, this guide is bad LOL
I understand jungle better now, though have no time to update it yet.Keeping for educational purposes, check the 2nd rated guide for better guidessss.

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As a starting note I like to play Olaf as a pretty risky Jungler. I try to use Berserker Rage to the fullest during my jungle, so focus is crucial to keep you alive. Also as I said it's risky, so be aware of the jungle and the lanes so there aren't any counter-jungles.
Also it's my first guide so any advice would be appreciated.
Also this will be a damage Olaf, which would be fairly tanky from armor, magic resistance and some health. If you follow this build, you should get lots of damage from your Undertow, and be able to finish off the enemy with your auto attacks and Reckless Swing
Please read the whole guide before voting down as it is not so short, and try it out as it does work if played properly. Also note that this is an offensive Olaf so if you like to play as a super tanky Olaf, this may not be for you. This is a tanky-dps, and is not built to completely tank damage, but just to sustain yourself.
Items under construction
Items under construction

There are 2 main jungle routes. The one I use is as shown.
Ancient Golem first, then Wolf, Wraith, Lizard Elder, Golem

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Ancient Golem- The reason I take Ancient Golem first is because of the blue buff. It would actually be pretty useful during your whole jungle, and simply because getting the blue buff would allow you to jungle smoothly, without any going backs as it is at the edge of the jungle.
Wolves- As I said getting this after the Ancient Golem would make it smooth, it gives you quite a lot of EXP. Pretty easy to aim your Undertow and easy to finish off.
Wraiths- The wraith is easy to finish off if your Undertow hits all of them. This may be a bit harder than the others due to the fact that there are 4 Wraiths, and hitting the blue one would be pretty challenging if not used to it. Either ways Wraiths doesn't deal much damage, therefore I believe it is easy to finish off despite the time.
Lizard Elder- Red buff. Very important, one of the key objectives of your Jungle. The reason I get this near the end is because you really want your red buff with you during your ganks, and getting it later would help it a lot. A very useful buff!
Golem- This is an easy target, gives you a lot of exp. One of my favorite monster in the jungle, and usually like to kill this even mid-game!
Play Video

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The alternative route (inspired by others, (fighter4143, PartyMagier and Koksei)) :P
I am not too fond with this route, therefore try at your own risk. It is harder than my main route, and a leash may be necessary (getting a doran's blade first should be nicer for this route)
Wolves first, Ancient Golems(Blue buff), Wraiths, Lizard Elder(Red buff), Mini Golems.
You would want a leash for Wolves and Ancient Golems.

When using Undertow place your cursor on yourself and adjust the direction. This would throw the axe very close to you, resulting to getting the axe without moving!
For Wraiths and Mini Golems, if you would auto-attack first then throw in your Undertow it would be a lot easier to hit all of the mobs.

I build Olaf as a tanky DPS. In jungling you can rely on your Tough It Out, but during ganking since it would likely not work well due to the duration and the difficulty in getting the time well. Therefore you would need to build on some life-steal after you end your jungle. Build some damage and life-steal early, and move onto health later on for more sustainability, as the enemy damage will be fairly high late-game.

I understand many of Olaf jungle guides would tell you to get some Vampiric Scepter first. But in this guide, as you can see, I start off with some Long Sword instead of Vampiric Scepter. This is to finish the jungle a.s.a.p and keep my health low as possible, to have better use of Berserker Rage. Also from many tries, I have worked out this would work the best for me. Since usually there won't be any counter-jungles early-game, therefore I'll say that keeping your self low on health wouldn't be a big problem, though if there are any counter-jungles, Ghost my save your life. Also make sure you have 1 health pot, during your red buff you could be too low on health, and if you're still not confident with keeping yourself alive, having 2 health pots won't hurt. Depends on your confidence towards your jungling.

Note: Even though Atma's Impaler is getting a nerf, please continue to use this item!
It would still be a great addition to Olaf!
Play Video

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Brute Force would increase my attack damage, giving higher damage output from auto-attacks and Undertow

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Butcher would increase damage on minions and monsters. This would increase damage output during your jungle. The reason I only take 1 point is due to the fact that I believe that other points are more useful than Butcher .

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Alacrity to increase my attack speed as my build are pretty much focused on attack speed and critical chance, along with resistance through armor and magic resistance. Attack speed is important :)

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Weapon Expertise , since monsters have armor aswell, armor penetration would increase your jungle speed. Not only does it increase your jungle speed, it would also be useful late-game killing champions with high armor aswell.

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Hardiness , is simple. Increase armor as monster deals physical damage, and increasing armor would decrease damage input on your champion.

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Tough Skin , I get 2 points into this instead of Butcher due to the fact that I believe Bladed Armor is very important in jungling, and you must have 2 points into Tough Skin to give a point into it. Also please note that a single health may put you between life and death, and even if these damage are stacked, it would not go as much as 1%, thus not being such a big problem to your passive.

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Durability to have some health, as my items aren't built on health, but more on armor and magic resistance aswell as damage. Some health would be required through masteries.

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Vigor to have some health regeneration while moving through the jungle, as without this, it would be HARDER to jungle.

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Veteran's Scars , same reason with Durability , to increase health of your champion.

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Bladed Armor is very important. This would allow you to deal damage on minions, while taking damage which would also increase your attack speed due to your passive.

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Initiator , this won't be so important early-game but as your health would be low pretty much all the time while jungling, but note that after you recall, it would allow you to get back into the jungle quicker.

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Honor Guard , this would decrease the damage input onto your champion against monsters and champions.

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Juggernaut , again you would like to increase your max health through masteries instead of items. This would keep you durable start and late-game.

Greater Seal of Armor Since this is a primary rune for seal, it would increase your armor by a lot, and armor is crucial in jungling therefore I suggest you to get armor for seals.
Greater Mark of Attack Damage Again a primary rune on mark. Increase your damage output by a lot, help you finish jungling quick.
Greater Glyph of Scaling Magic Resist This would keep your magic resist high on late-game, and this itself with force of nature would give you 100 magic resist, added with guardian angel with be scary for the enemy team as you have tons of armor aswell!
Greater Quintessence of Attack Damage This is a flat attack damage rune. This rune will keep your damage output high from the start of the game which allows you to jungle early.
Greater Quintessence of Scaling Attack Damage This is a damage per level rune. From trials, I found that the above rune is enough for my jungling, and to keep your attack damage higher at end-game I have chosen this rune. If you prefer, you may use a different rune instead of this Eg. Greater Quintessence of Movement Speed

Pros + Ton's of damage 8) + A great ganker + Ultra fast jungling + Tough It Out damage scaled to health

Cons - Requires aiming with Undertow - Requires thinking of distance with Undertow - Requires thinking of health with Reckless Swing - If Undertow is missed, your gank is pretty much a fail! :(

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Berserker Rage is your passive. I use the passive to the fullest. I keep my health low as possible yet keep myself alive during my jungle which would maximize it's effect. It improves your jungling speed drastically if used effectively and during fights, your passive could really flip the table around!

Description:
(Innate): For every 1% of his health missing, Olaf's attack speed increases by 1%

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Undertow is a skillshot axe. If you use this properly, the damage output is high. During jungle, using this after your w increases the damage a bit, but this technique could be not so useful during laning. The adjustable range needs thinking as you would usually like to have the axe in reachable range to reduce cooldown of this ability. This is your key ability during laning and thinking is crucial!

Description:
(Active): Olaf throws an axe to a target location, dealing physical damage to units it passes through and slowing them for 2.5 seconds. If Olaf picks up the axe, the ability's cooldown is reduced by 4.5 seconds.
Range: 1000
Cooldown: 8 seconds (with a 4.5 second reduction if axe is picked up)
Mana cost: 55 / 60 / 65 / 70 / 75 mana
Damage: 80 / 125 / 170 / 215 / 260 (+1 per bonus attack damage) physical damage
Slow: 24 / 28 / 32 / 36 / 40% slow

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Tough It Out is a temporary buff on-self. Buffs up your AD and gives you lifesteal and spell-vamp.
This is your key ability during your jungle. It gives you damage, and your passive will max out the damage input, and your lifesteal given by this would keep yourself alive during your jungle!

Description:
(Active): On active, Olaf gains bonus attack damage, life steal and spell vamp for 6 seconds.
Cooldown: 12 seconds
Mana cost: 40 / 45 / 50 / 55 / 60 mana
Bonus attack damage: 7 / 14 / 21 / 28 / 35 (+1% of maximum health)
Life steal and spell vamp 9 / 12 / 15 / 18 / 21%

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Reckless Swing is very important! It deals true damage and is very useful in finishing people off! Try not to use it too much in team fights as you may rage up people for ksing :) But yea, this could be very handy in fighting, but the fact that your health could go low if used too much could be hurting, and it also means you need some thinking.

Description:
Olaf attacks with such force that it deals true damage to his target and him self.
Range: 325
Cooldown: 8 / 7 / 6 / 5 / 4 seconds
Health cost: 40 / 64 / 88 / 112 / 136 health
True damage on enemy: 100 / 160 / 220 / 280 / 340

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Ragnarok is your ultimate! Use this skill carefully. Timing is crucial. You may want
to use this while your health is around half-way, and very useful during team-fights. I personally don't feel it's powerful at rank 1 but at rank 3 it is seriously VERY awesome!

Description:
(Passive): Olaf has increased armor penetration.
(Active): Olaf instantly removes all crowd control effects from himself. He is also immune to disables (including silences and blinds) and has increased armor and magic resistance for 6 seconds.

Cooldown: 100 seconds
Passive armor penetration: 10 / 20 / 30
Mana cost: 100 / 75 / 50
Armor and Magic Resist bonus: 30 / 45 / 60

The enemy may have bushes near the lanes warded so try not to stay in the bushes for too long. I keep watching the lanes, and when needed I run into the bushes, Undertow in before they can run, and run to them while they're slowed, pop my Tough It Out and carry some basic attack then BOOM! my Reckless Swing to finish em off. If they Flash away, just use your axe you picked up (yes try to pick up your axe) to finish em off. This tactic works even if their health isn't too low as Olaf deals "tons of damage" 8)

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These are places I usually ward!
Red have a high priority, and you want to ward it A.S.A.P.! These are places you want to ward, and would help your ganking quite a lot.
Blue have a high priority but less than red. It still would be quite useful but not as much. The reason I have the top bush labled as blue is because it would be harder to ward the bush! :P The top bush has the highest priority amongst the rest of the blue.
Yellow doesn't have such a high priority. I don't really like to ward the jungle very much. Though sometimes I do depending on how I feel~~! If you do, don't waste your sight-ward. If you would like to ward it, I would say use your wriggler's lantern, whichever blue or red you think is more important!
Purple! VERY high priority! Would be very useful to know when they are going to baron!

I get Undertow first, since it increases hits multiple monsters at a single time and deals lots of damage along with your AD runes! Then I get Tough It Out, to get some bonus attack damage and lifesteal. I would use my Tough It Out first, then use my undertow as the damage output would increase due to the bonus AD from your Tough It Out. I usually get a point into Reckless Swing to intentionally get myself low on health and deal true damage as it would be useful in ganks.
Undertow would be the most important in ganks, dealing tons of damage and having a very low cooldown if used properly (picking up the axe).
Reckless Swing is a very awesome skill as it deals true damage to the enemy, but on the other hand, it would also deal true damage to Olaf himself therefore it has a negative side aswell. Maxing Reckless Swing first would get your health too low in team-fights and such and would be TOO risky if used a lot, which would result to holding back the use of skill, thus not being so effective.
Tough It Out would be maxed LAST. Sure, it is a totally awesome skill, giving you damage and life-steal, improving your Undertow damage and giving you some heals. But I believe that Undertow and Reckless Swing should have a higher priority as Tough It Out would have a harder time using it effectively. I say it is harder due to the fact that it only buffs yourself for a short period of time, and the enemy can see your Tough It Out buff therefore able to take distance if too annoying, and if lots of point goes into Tough It Out it would become annoying, therefore using it would be a waste of mana if not used properly, and this would be very hard to use "properly" in my opinion.

Smite is COMPULSORY in JUNGLING. Deals instant big damage. Use early after your auto attacks as the gold output is gone (I believe), and try to use it on buff monsters or mini golems. (Some people don't use Smite in jungling, but trust me, you really need Smite unless you're Shaco (before the patch))

Ghost is very useful for Olaf. If your Undertow won't go in range, you can just
use your Ghost to run up to them, get yourself in auto attack range and use your reckless wing! Also if they DO go into your jungle early, you may use your ghost to run away from them.

Other choices

You may recall some time during your in-game, and Teleport would be handy to get you back in game. When there is a pushed lane, I sometimes just Teleport onto a minion to just give em a little scare :) Also if they don't go back too much just bash em your Undertow and get back to your business.


Some people prefer Flash than Ghost, therefore your option. But after the Flash nerf I think it is pretty useless and that Ghost would be much more useful.

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You may also want to take this, as this combined with your passive could give you ton's of damage output from basic attacks, and not only does it improve your basic attacks, it would also increase your Undertow damage output.

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Ok, many people seem to hate Phantom Dancer on Olaf but it IS a good choice. It gives you an attack speed bonus + increase your critical strike chance which is VERY useful if you are able to get into a long close combat match! It also gives you a movement speed boost which is useful when traveling, chasing, or ganking (if you get the item earlier)!

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Few words. Armor, health, awesome passive.
If you want to get this item, get it pretty early. It's fairly cheap, fair amount of armor and health, not too much but not too little. If you wanna engage combat, this item would be pretty useful. 35 damage may not seem much but I love it! Also the fire on your back looks cool 8)

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High damage boost, fair amount of attack speed bonus, cool passive!
Simple! When I have some gold left, I tend to buy B.F. Sword and I usually build it onto this~~! Yea when I'm feeling random that is~~

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Again, B.F. Sword builds onto this. Don't buy this item as much after the nerf! But pretty decent item, if you don't think you're gonna die much, then get this item! If you're deathless the passive could become VERY handy! Lots of health! Lots of life-steal!

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If you're building more onto life-steal this is very handy!
Also this with your Tough It Out could be pretty useful! Getting lots of heal from basic attacks and abilities (even smite!)

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Pretty cool passive, lots of armor and health and health regeneration!
Pretty useful, but not an item you want every game (for me atleast :P)

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You may want to get this item because the Passive is too awesome!
TOO AWESOME!!! Just kidding~ Don't buy this.. Now serious time~

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You may want to get Thornmail if enemies have lots of AD champions, or you would like to keep jungling late-game aswell. This item would not only keep you alive with maximum passive output, it would also allow you to turret-dive 8)

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NOTE:

Turret diving may not be an appropriate action. Please turret dive at your own risk

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ALTERNATIVE ITEMS

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So... you don't like Ionian Boots of Lucidity? Here are some GREAT boots that can be used as alternative of it!

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This item is GREAT for Olaf aswell as it gives you speed for Olaf, allowing to gank fairly easy, and chase fairly easy.. even flee easily!

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This item is AWESOME for ganking! If you stay away from combat for few seconds, you would have MASSIVE amount of movement speed~! Always a good choice for junglers!

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So.. many champions in the enemy team that deals magic damage?
Many champions in the enemy with crowd control?
Then this boot is always a choice!

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With the new dodge removal, I have stopped using Ninja Tabi as much!
Though it is still a great choice, and it is fairly cheap, can be built from cloth armor you might want to get while you're jungling! Definetely a good choice if you ask me!

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I'm not such a great player, so sorry for not having great histories :P
These are some histories I had at the time.

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Thank you XblueBlaze for allowing me to add your history!

Keep away from stunners early game!

You are NOT so tanky early-game therefore if you get enemies such as Pantheon and Jax early(before you get your ult), you're gonna get destroyed! Fight em after level 6, and don't hesitate to use your Ragnarok when fighting 'em!

#1 Change log created, 5/6/2012 :)
#2 Removed my friend's Kayle guide in credits due to guide being removed. 5/6/2012
#3 Simple changes, colors/bold words, some wording changes etc
#4 Simple changes again, with grammar and formality. 3/9/2012
#5 Minor changes due to s3 patch. Incomplete changes 17/12/2012
#6 SCREENIES 22/1/2013

Thanks to
Jhoijhoi for the guide to "how to create a build" and the funny karthus build :P
I also used Combatjack1's jungle template to show my jungle route so thanks to him aswell :)
http://leagueoflegends.wikia.com/wiki/Olaf for ability descriptions.
Thanks to moumoon for creating the awesome banner :)
Credits to XBlueBlazeX for screenies

This is my first guide, so I understand I have lack of BB codes, and it may be a bit unattractive. But if you do so give me advices, I will try my best to improve it.