Stuart Weitzman Boot Review: 5050 vs Alljack vs Highland

Over the past few years, Stuart Weitzman’s knee-high and over-the-knee (OTK) boots have exploded in popularity. These boots are extremely well-made and maintain their shape for years. However, it’s been confusing at times to keep up with all the styles – especially those that are newer to the scene.

I’ve owned a pair of black leather 5050s for several seasons and love how comfortable and versatile they are. Recently, I added a pair of black suede Highlands to the mix, but I was also curious about the medium-heel-height Alljacks in suede. I decided to put together a comparison of all 3 boots, since most reviews compare the 5050s, Lowlands and Highlands, but don’t really touch on the mid-heel ranged boots.

Stuart Weitzman Overview: 5050 vs Alljack vs Highland

Stuart Weitzman boots typically share similar characteristics with other styles – in this case, the 5050 and Alljack are actually most similar in style, classified as “knee height” with a front panel that is slightly higher than the back.

To make it easy, I’ve summarized this all in a chart:
Stuart Weitzman Boot Specs Comparison

Update Note: The Alljack has since been discontinued, however the Tieland has a similar heel height. 

Front View Comparison

Stuart Weitzman 5050 Alljack Highland Front Comparison
As you can see, the 5050 and Alljack look very similar from the front, except for the Alljack’s half-zip on the inside of the boot that makes it easier to pull on. The downside is that this zipper is visible from the front view (as shown above). Additionally, it’s not as form-fitting as the Highland, so the fit looks more relaxed.

Though the 5050 and Alljack are described as “knee height”, they both hit me right above the knee. For reference, I’m 5’4″ with a longer leg:torso ratio.

Side View Comparison

Again, the 5050 and Alljack look similar from the side, except that the stretchy back panel of the 5050 stands out in contrast to the leather front. In this photo, I left the ties hanging out on the Highlands – normally, I would tuck them in for a slightly cleaner look.

Back View Comparison

Same story here. You can tell from all three views that the Highlands are much skinnier in the ankle area, and are generally the most slimming of the three styles.

Toe Shape Comparison

Finally, an area in which the 5050 and Alljacks do differ! The 5050s have a more casual round toe, while the Highland boots have a slimmer almond toe. The Alljacks have an almond toe that is somewhere in between the 5050s and Highland – the difference is subtle, but it’s there. I ordered a 37.5 in all three boots, which fit similarly despite the difference toe box shapes.

Heel & Boot Height Comparison

Hiline vs Highland?

I ordered the Highland from Nordstrom’s winter sale and was surprised that they had them in stock, given the recent replacement of Highlands with the new Hiline style. I tried on both styles (unfortunately, no photos) – the only real difference between the two is the heel shape:

Highland (left) vs Hiline (right)

Personally, I preferred the Highland heel which is a bit more foot-slimming than the blockier Hiline heel. I felt that the Hiline shape made my already large-for-my-height size 7.5 feet look even larger, which I didn’t want. But I do like the overall look of the new Hiline – it’s a slightly more modern take on the boot.

Hope this post was helpful – and if you’re interested in tips on storing your Stuart Weitzman boots, check out my other post here!

Partnership Disclosure: This blog post was not sponsored by any of the brands listed above. As always, all opinions are my own. This post may contain affiliate links, in which I earn a commission on purchases.

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