For me, shopping is an art. The art of the hunt. For something to warrant the expense an item must fulfil an array of requirements such as quality, material, comfort, aesthetic and price. I do not believe in fast fashion. I believe in a collection of high quality basics, infrequently supplemented by trend pieces. Just for some occasional fun and freedom of expression.

With every purchase comes a period of wait and faith in the universe. The stars must align and it must be perfect. The perfect boot but not the right price? Nope. The perfect price but not the right boot? Nope. The perfect boot and price but lacking comfort? Nope. Nope. Nope.

Today I will present you with one of the best purchases I have made in the recent past. The Simone Boot from Vagabond Shoemakers. The perfect balance of all I seek when adding a staple piece to my wardrobe. Quality. Comfort. Style. Affordability.

The Simone Chelsea Boot is Vagabond’s fresh take on the western boot. Crafted from smooth black leather and featuring a slightly square-shaped heel, square toe and elasticated sides for flexibility and comfort.

The boot exudes a sense of luxury without the high ticket price. Simplicity and unique detail make them the perfect choice for a reliable black boot, adding a touch of style to any outfit.



The boots are made of leather upper, inner and lining, with a rubber outsole. The lining is made from 100% GOTS certified organic cotton. The insole is made from chrome-free tanned leather.

The quality of the craftsmanship is what I have come to expect from Vagabond, beautifully finished. The leather is sturdy but malleable, moulding to the foot over time, increasing comfort.


I am a fan of a clean, minimalist aesthetic with a focus towards elevated basic pieces. The squared off toe, the squared heel and the height of the boot are what caught my attention and are what maintained my interest.

I feel that they work perfectly alongside my beloved blazers (see previous post), trousers and just as well when adopting a more Parisian approach to fashion with a pair of jeans and a Bretton stripe or two.

A beautiful, delicate slip dress such as the one sported by Alessandra Ambrosio (by Orseund Iris -pictured right) acts as a wonderful juxtaposition to the more masculine, western details of the boots. Alessandra Ambrosio was pictured wearing the Vagabond Boots at the Milan Fashion Week in 2018.

It’s just a black boot, but not really. All the small details brought together make them just different enough to inject a little bit of je ne sais quoi into any outfit and THAT is what makes them a good piece to add to my wardrobe.


As for the price, I am a bargain shopper. I never pay full price. As a rule of thumb I will typically only purchase items at a 50% or more discount. This does mean that shopping does require a lot of patience.

I will hunt for a piece I like then wait until discounts, and often further discounts roll around. If the price still isn’t right I will just keep waiting, or ultimately take it as a sign it was never meant to be and start the search all over again.

Paying full retail prices is unnecessary, as if there is enough space for the price to go down, the profits are massively maximised through price gouging.

These boots retailed for AU$250 on ASOS

Purchase price AU$125


The most important requirement of all, comfort. The heel, standing at 55mm is the perfect height, never causing my feet to ache. I have spent full days standing at work with no issues which is a huge bonus, and enough for me to become a devoted life partner to my Simone boots.

The one issue I find with taller boots, especially with higher standing ones such as these, is that they will rub where the boot sits close to the calf. I will typically wear higher socks to prevent this before it ever gets the chance to happen. Comfort above all.

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