Introduction 
One of the biggest struggles I've had with wearing lolita fashion is finding the right footwear that is stylish enough to match with the coord and comfortable enough to wear for an outing. Most of the time, I opt for style over comfort— I don't wear lolita in my day-to-day life, so I'd rather endure the discomfort for a little while than go out looking uncoordinated
Damage reduction via insoles, heel protectors, and taping can only go so far when your shoes aren't built for practical use... And it wasn't until I discovered the concept of orthopedic Mary Janes did I realize it was possible for shoes to be both practical and cute!
I discovered the brand Alegria thanks to Mala's suggestion, though there are plenty of other brands out there that make cute orthopedic shoes! I decided to purchase from Alegria since reviews online (cough reddit) cited good reviews from their products.

Product Information 
Product: Jazmine Black Nappa ShoeColour: Black Nappa (Matte Black)
Material: Leather, polyurethane outsole
Size: US Size 8-8.5 or Euro Size 38
Product Cost: $169.89 CAD
Total Cost: $314.58 CAD* 
*Total cost includes shipping and customs.

Sizing and Fit 
The shoes ended up a little bigger than the usual Size 38 footwear I get from Asia. The sizing is not significant enough to warrant a replacement, and the extra space makes it suitable to wear with socks. In my opinion, it's better to have a shoe that's slightly too big than slightly too small— for example, my mary janes from Antaina are a little too small, which make them very uncomfortable after prolonged wear.
Back to the Alegria shoes, the upper top-line of the shoe feels a little stiff without socks on. It's not too uncomfortable and with frequent wear I presume the leather will soften and break in over time.

General Review 
These are probably the most expensive shoes I have in my wardrobe
A majority of the cost went into shipping and import fees that could've been avoided had I bought the shoes from a brick and mortar store... Unfortunately, the nearest shoe store that stocked Alegrias did not have the model I was looking for.
My heart was set on the Jazmine Mary Janes, and if I was going to drop ~200$ on a pair of shoes, I would like for it to be in a style that I actually enjoy wearing...
And wear them I shall, as the Jazmine Mary Janes are very versatile and easy to style! They're simple enough to be worn in casual coords outside of lolita, and I could probably even wear them to work with how low-key they are!
My favourite feature of the shoe is the orthopedic footbed. It's shaped to provide optimal support for your foot arch, making it very soft and squishy! I frequently feel discomfort and even pain in my arch when I wear shoes without insoles, so it's really nice that the footbed came included with arch support.
The shoe is fastened with velcro strap that can be adjusted via a hook and loop clasp; I find the velcro much easier to clasp and unclasp compared to the traditional metal buttons that are common in lolita shoes.
Although the brand boasted a zero-break in period, the upper part of the shoe feels stiff and hard against a bare foot, which makes it a little uncomfortable for walks. Currently, they work best paired with socks.
Coordinate 
Headpiece: Rose Lace Rectangle Headdress - Zero Percent Fruit Blouse: Short Sleeve Waist Shirring Blouse - Baby the Stars Shine Bright
Cardigan: Sweet Alyssum Series Knit Cardigan - Vallée lys
JSK: Anna Rose JSK - Alice and the Pirates
Wrist cuffs: Star Lace Wrist Cuffs - Zero Percent Fruit
Ribbon Bowtie: Off-brand
Socks: Velveteen OTK Stockings - Roji Roji
Shoes: Jazmine Mary Janes - Alegria
Despite waking up later in the day, I decided on a whim to finally go out in lolita! I took my sister along on a small outing in town: We stopped by the library to check out a book and renew her library card. We arrived just in time since the library was going to close in 10 minutes!
Afterwards, we went to a cafe to eat lunch and have yummy drinks. The owner is a sweet young woman who also dresses in alternative fashion! Her cafe is a designated safe spot for me to wear eccentric clothing, and the food + drink is delicious to boot!
Today I decided to splurge and order a sized-up drink with a big bowl of soup to share between me and sister.
It was a wonderful day, and it feels all the more lovely with cute clothing on! Having practical shoes that felt comfortable on my feet elevated the experience as well!

Verdict
Overall, I'm very satisfied with my purchase! It was a pretty big splurge though, and I foresee a no-buy until the New Years haha...
I think I went a little crazy on online purchases this September— these shoes being the culmination of it... Finally having an income to spend on personal interests again is so freeing! But also very very dangerous
But I can at least wear these shoes in a semi-regular basis unlike a majority of my lolita splurges!
I'm very excited to wear these shoes in my day to day life!

cheerful
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