The evolution of the Alaska airlines livery has been very interesting. It started out in the 1960s as something very regional and niche specific. Today, it’s one of the most recognized brands across the entire United States.
The original Eskimo livery: 1976-1990
Alaska Airlines unveiled in all new livery in 1976 that would define it’s brand image for decades to come. The key element of this livery was the depiction of the Eskimo character on the vertical stabilizer of all its aircraft.

The 1976 Alaska Airlines livery over top of my Boeing 727-200 template
This Eskimo, commonly referred to today as “Chester”, was a significant departure from the rugged outdoorsman it replaced in the previous livery.
Two separate thin lines of color ran down the entire side of the fuselage one (a green one above the windows and a blue one below). They met at a point near the cockpit windows.
Just as it was in the previous livery, the Alaska typeface remained bold and simple. This was a custom font, but it was largely based on Helvetica bold.
The Icicles livery: 1990-2016
Alaska airlines unveiled an all-new livery in 1990 which was a stark departure from the previous one. Interestingly enough, all of the elements from the previous livery (the stripes, the Eskimo, and the single Alaska titles) remained. They were just rearranged slightly.

The 1990 Icicles livery on my Boeing 737-800 template.

This livery looked pretty good on shorter aircraft as well (as seen here on my Boeing 737-700 template).
The biggest change was the style of the “Alaska” font on the forward section of the fuselage. This new version was much larger, and featured a custom (more rugged) typeface more representative of Alaskan culture. Many referred to these typeface looking like icicles (and thus resulting in the nickname for this livery).

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The stripes were pushed down the bottom section of the fuselage. They were also made with varying thicknesses (the green line was thinner), and were connected down the entire length of the aircraft. The dark blue color was replaced with black.

Fun fact: when to celebrate the launch of service to Hawaii, there was a modification to the original Icicles livery which featured a red Lei around the base of the Chester (Eskimo) graphic on the vertical stabilizer. There were only a handful of 737-800’s which featured this special livery.
Updated Icicles livery: 2015
The biggest feature of this update was the modernization of the Alaska Airlines typeface – to put it in the simplest terms possible, they smoothed out the font to look more modern (and a lot less like icicles).
They also replaced the black accent colors with dark blue, which to be quite honest, is difficult to even notice unless you’re looking at the airplane under direct sunlight. It’s so dark as a matter of fact, that it still looks black under overcast conditions . I never would’ve even known this if I hadn’t found a slightly over exposed picture on the Internet of an airplane wearing this update. Who says over-exposed pics are worthless?

Side by side comparison of the 1990 Alaska Airlines “Icicle” livery and the 2015 “updated” version on my Boeing 737-900/ER template
Additional modifications included the removal of the green outline around the portrait of the Eskimo (Chester) on the vertical stabilizer, as well as an intricate (and swoopy) version of the dark blue and green stripe on the winglets.
Overlapping colors livery: 2016-present
In 2016, the Alaska Airlines livery changed yet again. This was easily the most significant livery update in the history of the company, featuring a bold departure from traditional Alaskan design elements. It was also pretty good timing considering that they would be soon need to begin repainting aircraft in the Virgin America livery to Alaska Airlines. Might as well start with an all new design, right?

The all-new 2016 Alaska Airlines livery (seen here on my Boeing 737-9 MAX template).
I wrote an entire post about the new Alaska livery, and I’d recommend reading that to learn more about it.