Being a contender for friend-of-the-year award, I did some research!
Here's another image of it from google, slightly more pointy, but plain
After searching for Chelsea boots, I have identified there are 3 categories
1. The plain
2. The brogue
3. The buckle
I'd categorise my 2 toned balenciaga as plain. Here are a few more plain Chelsea
Alexander Wang $495 (barneys.com)
Although a little unconventional, I like the shape of the toe a lot as well as the chunky edgy heel detail, the height of the shaft seems shorter and looks like it'd sit little below the ankle, which is perfect for streamlining the legs~
Rag & Bone $415 (barneys.com)
Enlarging the Chelsea boots 'elastic band' detail, the Rag & Bone has quite a nice vintage look to it, especially the wash of the wood around the heels too, taking away the "HELLO!? I AM WEARING NEW SHOES" embarrassment! (I always remember loving new shoes but hating them looking so new from a very very young age, think I even told my mum that and she thought I was rather odd..) I think this is a nice simple pair to have and quite timeless too.
Burberry $950 (netaporter.com)
This I thought has all the classic chelsea boots elements to it, they even have nice leather details on the elastic band part.. but what really put me off was the over done studded detail.. looks a bit like a bunch of mini fungi or.. polka dots... nah.
Robert Clergerie $695 (barneys.com)
This I think it's very nice and has subtle details to it.. e.g. the brogue-like trimmings, simple, classic!
Saint Laurent $885 (barneys.com)
I LOVE this pair, I had been searching for black leather til I saw this, and it actually dawned on me that non black ones; possibly suede, would run less of a risk of the shoes looking too manly. This, is perfect, no gimmick, plain simple and timeless. Suedes are harder to keep in rainy weathers, just remember to spray the protector before hand then it's all good, AND they are so soft!!!
Brogue is a style that has really grown on me over the years; originated from Scotland, used to be made with untanned hide with proliferated detail to allow water to drain from the shoes when crossing wet terrain. I think it serves more of a decorative purpose nowadays.
Balenciaga $795 (balenciaga.com)
Balenciaga has some really really great ankle boots, prices are all pretty hefty though. This particular style is very comfortable to walk in, and just like the bags they do, there are different colours every season. The supple distressed leather is lovely. Love the single stud detail on the back.
Bottega Veneta ($950 netaporter.com)
Stunning colour with beautiful stitch detail on the cap where the brogue is. It's missing something though for me..
Church's ($560 netaporter.com)
Church's was the first brand I looked for when I started the whole chelsea boots search, they are just so textbook when it comes to shoes-with-a-history! And they are beginning to bring out more and more styles that's very classic English with modern twists or elements in them without over doing it (like those Burberry)
The shaft height is perfect, nice curved details on the elastic band.
The brogue is just stunning! A true classic in design, i'd probably opt for a more matte pair.
Church's ($735 netaporter.com)
Almost identical to the above but with more dynamic studded details, nicely done. Subtle, but quite cool.
ASOS ($85 asos.com)
With the primary currency being pounds sterling, the price on asos is always a bit odd here in the states. This is the more frugal choice, kinda of like the less refined child of the churchs and bottega. Not bad if you were looking for something with a higher shaft.. if you opt for lower like me.. then
ASOS ($54 asos.com)
I LOVEEEEE LOVE LOVE this pair, it's the perfect of everything I would like and at a great price point too!! (think it's on sale right now). The distressed / vintage look is great, the colours fantastic and ok the brogue may not be as detailed as the church's, but at $54 I wouldn't complain!
Some of the buckled ones run the risk of looking a little manly i think, they are nonetheless a great accent.
balenciaga papier ($915 balenciaga.com)
I know the name of this pair coz I have been drooling all over them for over a year now, they looked SO chic on! the leather so soft and the buckle is just right, very slimming!
church's ($575 netaporter.com)
Those are a little bulky, and too shiny for me, and a little manly..
The next 2 pairs are like the taller and shorter non-identical twins, very frugal, I actually like the kg a lot.
kurt geiger ($125 asos.com)
River island ($47 asos.com)
Robert de Carlo ($665 barneys.com)
Neatly designed, with a bit but not too much of everything. A little buckle, a little brogue, and the tongue is quite a nice addition to a otherwise plain pair of boots. I like it!
zara ($99 zara.com)
NICE DEAL!!!! a little "inspired" by the saint laurent, but in a good way.
Whistles ($275 whistles.co.uk)
This is quite an interesting pair for me as it has the beige, suede element from the saint laurent that I liked as well as the buckling style of the balenciaga papier. Not bad at $275
THANK GOD those were the only ones I found that I felt was worth mentioning, friend-of-the-year award? haha
Given the choice I would have gone for the frugal asos brogue and the balenciaga papier. I am a little on the shorter side, so if the boots covers too much above my ankle it'd make me look like a hobbit. My friend D, on the other hand, is THE tallest girl I know at over 6ft, olivia pamelo look alike (as i've recently discovered and have not told her) skinny and stunning! If you are reading this, and you should haha, you, really can pull off anything.. honest!!