Roadmap

Stage 1: Legendary Trophies Delete

The "Legends" game update added three trophies, two of which are very easy, you'll be able to do them both during the storyline. They basically require you to buy two cars and take them out on the streets to win events with them, be sure to have some space in your garage for them!

After getting those trophies, it's time to focus on the Mental Unlock trophy, this will likely be the trophy that's responsible for most of your time spent with this set of trophies, definitely take a look at  Mental Unblock for helpful tips on mastering that event.

Trophies you should work towards in Stage 1

• Fanboi
  Put Ken's or Morohoshi's car in your garage
• Iconoclast
  Win events driving Ken's and Morohoshi's cars
• Mental Unblock
  Get a 350000 Drift Score in Mental Block with Ken's car

Stage 2: Iconic Trophies Delete

The "Icons" update was added to this game on December 9, and interestingly enough, this update added three new trophies to this existing DLC trophy pack, those trophies being  Eddie is Back,  Zero to Hero, and  Hit the Ceiling.

This update requires you to finish 15 new events called "Eddie's Challenges" to get two trophies, and then get to Rep Level 70 to get the last trophy. Because of the odd nature of how these trophies were added to an exisitng DLC pack, the guide system wasn't designed to handle that specific situation. That issue will be resolved in the future, but until then you can see tips and information for these trophies in the Additional Trophies section of the guide.

Trophies you should work towards in Stage 2

• Hit The Ceiling
  Reach REP Level 70
• Eddie Is Back
  Complete Eddie's Challenge
• Zero To Hero
  Win an event in Eddie's Car

Additional Trophies

[Note From The Guide Team] Because of the odd nature of the developers of this game releasing new trophies onto an existing DLC trophy list (which hasn't ever really happened before in any other game), the guide system was not designed to be able to check for additional trophies for an existing list. To resolve this, it will require some tinkering with the code and it will be fixed soon, but for now a short summary of the additional trophies will be listed here. 

Icons Update - Eddie's Challenges & Rep Level 70

On December 9th, trophies were added to this DLC list accompanying a new free update to the game. The update added 15 new "challenges" (racing events) to the game called "Eddies Challenges". After updating the game and starting it up, you'll immediately get a call in the game from a person named Melissa informing you about the challenges if you're past Rep Level 25, a few minutes later you'll get texted saying that Eddie's app is installing onto your in-game phone. A few minutes after that you'll have a fourth app where you can launch all of Eddie's Challenges from.

After you complete all 15 of these new events, you'll earn the  Eddie is Back trophy. Once you earn that trophy, you'll unlock the ability to purchase Eddie's car (Eddies Nissan Skyline GT-R V-Spec), which can be purchased from the garage. Buy Eddie's car and then win any event with it to obtain the  Zero to Hero trophy.

Once you finish all of Eddie's trophies, the last trophy requires you to get to Rep Level 70. The level cap when the game released was 50 and now its been raised to 70. For tips on how to level up quickly, see the  Can I Get Your Autograph? trophy from the main games trophy guide. Once you reach level 70,  Hit the Ceiling is yours. Fanboi
Put Ken's or Morohoshi's car in your garage 98.13%
Common For this trophy you should purchase two cars - Ken's (Style) Hoonicorn Ford Mustang (1965) and Morohoshi's (Outlaw) Lamborghini Diablo SV (1999). Both cars are free.

Like in the original game where you were given two free cars for progressing through the story (Nakai-San's and Magnus's), this game update adds two new cars. If you've already finished the storyline and are re-entering the game, these cars should already be available to purchase in the garage. If you haven't finished the story, these cars will be unlocked at some point while progressing the storylne. These cars are not necessary to purchase for finishing the game, however if you're going to get this trophy, you'll need to buy one of them.
  Ken's Hoonicorn Ford Mustang (1965) Morohoshi's Lamborghini Diablo SV (1999) Iconoclast
Win events driving Ken's and Morohoshi's cars 55.14%
Common As the trophy description says, you should win any event while driving Ken's Hoonicorn Ford Mustang and then win an event while driving Morohoshi's Lamborghini Diablo SV. Simply get these two cars once you unlock them via the main story, find any easy event you'd like, and win it with both of the cars.

For the information about purchasing these cars, see the  Fanboi trophy. Mental Unblock
Get a 350000 Drift Score in Mental Block with Ken's car 29.93%
Uncommon Time Limited
This trophy is likely to be the hardest one in the entire game. To do this, you should purchase Ken's (Style) Hoonicorn Ford Mustang, which is unlocked later in the story. Now go to the Mental Block Gymkhana event (it's the last event you'll unlock in the Style storyline and it's located in the Crescent Mountains on the top-right of the map) and go on to achieve a score of 350,000 points in the event.

This race has two main "sections" it can be split into, the first section has you driving in the mountains, the second section is in the city. It's highly recommended to have at least (or very close to) 250,000 points by the time you enter the city (you'll go through the underground tunnel). If you have less, it's best to restart the race because the second part is more difficult to get points.

To get a lot of points, you'll simply want to hit turns hard and fast, there is literally very little time on the clock that allows you to slow down, so you'll need to take turns nice and quick, no "over-driftng" or heavily milking turns for more points as that will drastically slow your car down. You'll want to tap  when going around big turns, but definitely stick with pressing  when going around hard turns (even some medium turns). Your drifts are harder or softer depending on how long you hold the  or  buttons too, so you'll definitely want to get a feel for that.

Do keep in mind that when you're taking the few straightaways in this event like the construction zone in the city to use your nitro by pressing , doing that shaves valuable time you could spend drifting. You may find that pressing  and changing your view to the tailing-drift view (the view that sways to the side of your car as you drift) might help you significantly with this event. Hitting walls and cars usually cause you to loose a considerable amount of points you're getting mid-drift, so be sure not to do that either. If you end up getting 350,000 a few checkpoints before the finish line, then stop focusing on drifting and focus on reaching the end as quickly as you can without wrecking.

This trophy's high score requirement along with this event's ridiculous time requirement of 6:45 will likely have you repeating this event several times. Eventually you will get the speed and flow of the event and reach 350,000 within the time limit. The trophy will pop once you reach the finish line within the time limit with more than 350,000 points.