The Latte flip came out of that weird time in the early 2000s where a new generation of freestylers were finding each other on the internet and sharing postage-stamp sized videos of the stationary tricks they were inventing in their garages over 56k dialup connections. It was a glorious era for bizarre and disgusting flip tricks, but this one – basically a heelflip out of heelside rail, invented by Jeff Ryker – has always been a favourite of mine. It’s fiddly but very satisfying when you get it right.
You might think you’d want to know how to heelflip before you learn the latte flip, but oddly, that might not help you much – this is different enough that knowing how to heelflip might throw you off.

You want to start this trick in the same position as you’d be in for a butterflip – the front foot is stood on the back wheel, and the back foot is positioned in the exact same place it needs to be for a regular railflip. How you get here is up to you.

Here’s what that looks like from in front. Notice that I’m positioned so that my centre of gravity is very slightly behind the back truck and I’m already bending at the knees and compressing for the jump.

As I start the trick, I have to push my back foot down and forwards slightly – big emphasis on slightly, there – to start the board tipping into a position where my front foot can connect with the griptape. If you’ve already learned the reintges flip, the way the board rocks into position should feel fairly similar to that.

I didn’t realise until I saw the sequence how much my front foot position here looks like an ollie. That makes sense, as I’m really aiming to get as close to a heelflip motion as I can. The gap between my foot and the griptape isn’t ideal – you want to try to get in contact with the grip as soon as possible. The bigger that gap is, the worse the latte flip will be.

By now I’ve reconnected with the deck, and I’ve got full contact with the grip. If you left the board too much for too long, there’s a good chance that you’ll just thud into the deck here, punting the deck down towards the ground. You want to try to make this motion as smooth as possible.

It’s tough to tell from this angle, but the side of my foot has slid out the side of the nose like it would for a heelflip. Note you need to use a proper heelflip technique here – don’t poke at it with your toes or you’ll just kick the board away. Try to use the outside of the foot and heel.

From this angle you can get a clearer picture of where I’m leaving the board. Watching this now I can see I’d probably have got a better and higher flip with a kicknose due to how my foot slides out end of the deck, but the advantage of the square tail of Moonshine’s Kill Your Idols deck was too good to pass up.

Having disconnected from the deck completely, all I can really do is hang above it. I could have skipped this frame apart the fact from you can see clearly how my front foot has kicked straight forwards for this one, re-confirming the heelflip motion. If you’re only getting the flip from the pop of the back foot, you’re not doing a latte flip.

And now I really am just in “hang and wait” mode. This could be a textbook heelflip photo if the setup for the latte flip hadn’t put me so far towards the back of the deck – something that will come back into play in a second.

Okay, there’s a lot to unpack here. Firstly, I’ve not connected with the deck smoothly enough and it’s starting to over-level and nose-dive towards the ground. Big oops. Also, as I just mentioned, that starting position has led to me coming down more or less where I started – namely too far back. That’ll need correcting – and fast…

…so having used my back foot to push the tail down a bit and correct the board’s angle, I’m also going to have to move my front foot back up towards the nose to prevent myself from shooting out on the landing.

Having pushed all four wheels back to the ground, I’ve also shifted my weight slightly forward and centred myself over that front leg. Not only is this another anti-shoot-out technique, but it’ll put me in a far better position for whatever trick I want to do next.
Additional Notes
Okay, the first note should be obvious by now: this is a rail trick. Use freestyle wheels. Unlike when this trick was invented, freestyle wheels are easy to get hold of and will make your life a lot easier. There’s really no reason to not be using them if you have any interest in freestyle tricks.
Also, like a lot of rail tricks, stiffer trucks will also make your life a lot easier, as you’ll get a lot less wobble during the set-up for the flip. If you’re still using stock bushings, it’s time for an upgrade. Barrel-and-cone combinations are basically mandatory – double conical setups never have enough stability for things like this. Durometer will depend a bit on your body weight and the climate, but I recommend 95a at a minimum.
However, unlike most rail tricks, the latte flip might benefit from a lower setup, and not a taller one. I say might because I haven’t tested it, but my thinking is that you’re more likely to connect with the griptape than the rail as the ratio between deck width and setup height shifts to be more in favour of the width. This is all going to be a trade-off, as a lower setup will be more unpredictable when you’re actually preparing for the trick, but hey, it’s worth trying out.
Deck shape is also going to be a factor here. The reason I took the single kick setup out for a play is that the square tail gives you a far more consistent and reliable starting position and a better “pop”; tapered tails (like most modern double kicks) can be a bit twitchy on the take off, and a rounded tail (like on a street deck) will want to roll around so much that you’ll have to be very fast with the front foot to connect with the latte flip and not just do an awkward railflip with the back foot.
The last note isn’t really to do with the latte flip directly, but it is a fun extra titbit of information: if you use the latte flip concept to do an ollie kickflip from toeside rail, the resulting trick is called a mocha flip. The only person I’ve ever seen do one is Jeff Ryker himself, so if you like the latte flip and fancy a challenge, give the mocha flip a go and tag me in a video of one on Instagram. There is no prize for doing so, but you will win my eternal* respect.
* note that said respect can and will be revoked in response to horrific actions like racism, homophobia and egregious no complies.
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