Help me decide: ankle bootie edition

[anastasiya26]

Hi there,

I’m torn between the Saint Laurent Ashley ankle boot in a sophisticated, skinny heel silhouette, and the more practical Jill block heel version. I tried both on over the weekend and they’re both surprisingly comfortable, with Jill being the most comfortable.

Although Jill seems more practical, I really fell in love with the aesthetics of the stiletto one. I want a versatile style that is dressy enough to wear out at night, but also practical enough to wear during the day with a fair amount of walking. Does anyone have experience with a similar stiletto bootie that can speak on if you get any daytime outdoor use out of it?

Any other opinions or advice welcome! Thank you!

Note: In the 2 photo side by side, I’m wearing one of each to compare the toe box shape. The pointier toe is the stiletto style.

 

[papertiger]

You can definitively get away with the Ashley aesthetically. They look soooo cool and high-fashion on you.

I think you will regret not going with your if you go

 

[jellenp32]

Both are so close, until the heel. I would think the more substantial heel would be more comfortable for long walking

 

[lill_canele]

Being a longtime YSL shoe lover I like both.
Usually I’d go for the one with the higher heel (regardless of the stiletto shape) because I love high heels but I see they’re about the same height.

Since I already have a blockier heel boot from YSL I’d go for the Ashley lol. Sorry, I know that’s not helpful.

In terms of practicality I will say Ashley has a relatively high chance get caught in sidewalk cracks, and escalators. And be careful of walking on stairs that have openings or grates. (Learned this from experience of wearing many thin stilettos)

I asked my husband his opinion and he said: they’re very similar and serve the same purpose.
But the vibe is different.
Ashely is more dominating and strong.
Jill is more reserved and sophisticated.

 

[anastasiya26]

Being a longtime YSL shoe lover I like both.
Usually I’d go for the one with the higher heel (regardless of the stiletto shape) because I love high heels but I see they’re about the same height.

Since I already have a blockier heel boot from YSL I’d go for the Ashley lol. Sorry, I know that’s not helpful.

In terms of practicality I will say Ashley has a relatively high chance get caught in sidewalk cracks, and escalators. And be careful of walking on stairs that have openings or grates. (Learned this from experience of wearing many thin stilettos)

I asked my husband his opinion and he said: they’re very similar and serve the same purpose.
But the vibe is different.
Ashely is more dominating and strong.
Jill is more reserved and sophisticated.

Thank you for the thoughtful answer! The Ashley is about .5” higher. Do you still walk around in the city in your thin stilettos a light amount? Say for a coffee stroll with a friend, several blocks from one bar to another, etc.? Prior to this boot, I exclusively wear my heels from a car to the destination so I really have no sense on how much walking these can withstand without mishaps like getting stuck or inflicting damage to the heel.

Which YSL block heels do you own?! I wish I could buy both!! But this will be a Christmas gift from my husband so I really have to choose. I like your husband’s take about the vibe! It’s interesting, I interpreted the stiletto as the more classic, sophisticated one, while the block heel feels more edgy (probably because I associate it more with street style). I am so torn between the peace of mind of the practical one, and the giddy feeling I get when I think about the stiletto!

 

[anastasiya26]

You can definitively get away with the Ashley aesthetically. They look soooo cool and high-fashion on you.

I think you will regret not going with your if you go

I think you’re right about that!

 

[lill_canele]

Thank you for the thoughtful answer! The Ashley is about .5” higher. Do you still walk around in the city in your thin stilettos a light amount? Say for a coffee stroll with a friend, several blocks from one bar to another, etc.? Prior to this boot, I exclusively wear my heels from a car to the destination so I really have no sense on how much walking these can withstand without mishaps like getting stuck or inflicting damage to the heel.

Which YSL block heels do you own?! I wish I could buy both!! But this will be a Christmas gift from my husband so I really have to choose. I like your husband’s take about the vibe! It’s interesting, I interpreted the stiletto as the more classic, sophisticated one, while the block heel feels more edgy (probably because I associate it more with street style). I am so torn between the peace of mind of the practical one, and the giddy feeling I get when I think about the stiletto!

Oh when I wear heels I wear them all day! I drive with them, cross streets, go up and down stairs, the whole 9 yards lol.
I have no backup shoes or flats with me. I deal with the pain, blisters, and numbness if they happen.

The pair I own is old-ish, from 2017 or 2018 and they're a thicker block heel than the Jill (different times, different style) but they're on the taller end of the spectrum. I was lucky. They retailed for $2000 USD (at that time that was quite expensive for designer boots) and I got them half off at the private sale.
Btw, those boots took 2 seasons to break in. They were a very very stiff leather. I felt like my toes were being cut off whenever I wore them. They're great now though, my iron boots that can withstand anything!

I see online that the Jill comes in 2 heights. 9.5cm (3.7in) and 7.5cm (3in).
The Ashley I only see a 9cm (3.5in) height.

If I were you (and didn't have another pair), I'd go for the taller Jill of 9.5cm/3.7in. Mainly because I like height.

However, this really depends on how comfortable you are walking in high heels and thin stilettos.
I am quite used to both and I even stand on my toes when taking an escalator to avoid them getting stuck in between the metal grills. (actually just sent in a pair of CL 100mm very thin stiletto heels for repairs because they did get stuck when I leaned back by accident and ripped the bottom point off)
If you are either a relatively experienced stiletto girl or you're willing to go the extra mile, then go with your heart!

On a side note, YSL shoes in general are not for the weak of heart or feet. I have bought pairs that felt great in store only to be limping in them after wearing them for half a day. I also have slim/narrow feet and tend to fit in most YSL heels/shoes in general but even then, I have to break them in or get used to them.

 

[Berengeria]

I am so torn between the peace of mind of the practical one, and the giddy feeling I get when I think about the stiletto!

Go with the giddy feeling. That's your heart talking. The peace of mind, is just that: the mind. When it comes to shopping, the brain has no business getting involved until it comes time to pay the bill. Until then, it needs to be quiet and let the heart do the talking.

 

[anastasiya26]

Oh when I wear heels I wear them all day! I drive with them, cross streets, go up and down stairs, the whole 9 yards lol.
I have no backup shoes or flats with me. I deal with the pain, blisters, and numbness if they happen.

The pair I own is old-ish, from 2017 or 2018 and they're a thicker block heel than the Jill (different times, different style) but they're on the taller end of the spectrum. I was lucky. They retailed for $2000 USD (at that time that was quite expensive for designer boots) and I got them half off at the private sale.
Btw, those boots took 2 seasons to break in. They were a very very stiff leather. I felt like my toes were being cut off whenever I wore them. They're great now though, my iron boots that can withstand anything!

I see online that the Jill comes in 2 heights. 9.5cm (3.7in) and 7.5cm (3in).
The Ashley I only see a 9cm (3.5in) height.

If I were you (and didn't have another pair), I'd go for the taller Jill of 9.5cm/3.7in. Mainly because I like height.

However, this really depends on how comfortable you are walking in high heels and thin stilettos.
I am quite used to both and I even stand on my toes when taking an escalator to avoid them getting stuck in between the metal grills. (actually just sent in a pair of CL 100mm very thin stiletto heels for repairs because they did get stuck when I leaned back by accident and ripped the bottom point off)
If you are either a relatively experienced stiletto girl or you're willing to go the extra mile, then go with your heart!

On a side note, YSL shoes in general are not for the weak of heart or feet. I have bought pairs that felt great in store only to be limping in them after wearing them for half a day. I also have slim/narrow feet and tend to fit in most YSL heels/shoes in general but even then, I have to break them in or get used to them.

I think you and I may have similar shoe taste and feet! I have narrow feet as well (with a narrow back heel) and YSL is one of the only brands I've found that are comfortable in the store! Most shoes from other brands are either too big in the heel or too small in the toe box and pinch from the start. I have the Opyum pumps, which was my first Saint Laurent style and these are unfortunately very uncomfortable, but the Anja pump in patent and smooth leather is my go to trusted heel. That said, this is for nights only - I still couldn't last in them for longer than five hours with minimal walking.

I'm also sorry to hear about the CL stilettos!! Hope they come out of repair as good as new! I don't think I am daring enough to brave the escalator in a stiletto quite yet!

Go with the giddy feeling. That's your heart talking. The peace of mind, is just that: the mind. When it comes to shopping, the brain has no business getting involved until it comes time to pay the bill. Until then, it needs to be quiet and let the heart do the talking.

Thank you for this! I really think you're right. And thank you to everyone for your great advice and for entertaining this decision for me! I've decided to listen to my heart and go with the stiletto version! I've accepted that I may just need a more practical but chic walkable heel anyway, but for right now, I get more excited about the thought of wearing the thinner version out at night, even if it might not get as much use during the day.

 

[anastasiya26]

Oh when I wear heels I wear them all day! I drive with them, cross streets, go up and down stairs, the whole 9 yards lol.
I have no backup shoes or flats with me. I deal with the pain, blisters, and numbness if they happen.

The pair I own is old-ish, from 2017 or 2018 and they're a thicker block heel than the Jill (different times, different style) but they're on the taller end of the spectrum. I was lucky. They retailed for $2000 USD (at that time that was quite expensive for designer boots) and I got them half off at the private sale.
Btw, those boots took 2 seasons to break in. They were a very very stiff leather. I felt like my toes were being cut off whenever I wore them. They're great now though, my iron boots that can withstand anything!

I see online that the Jill comes in 2 heights. 9.5cm (3.7in) and 7.5cm (3in).
The Ashley I only see a 9cm (3.5in) height.

If I were you (and didn't have another pair), I'd go for the taller Jill of 9.5cm/3.7in. Mainly because I like height.

However, this really depends on how comfortable you are walking in high heels and thin stilettos.
I am quite used to both and I even stand on my toes when taking an escalator to avoid them getting stuck in between the metal grills. (actually just sent in a pair of CL 100mm very thin stiletto heels for repairs because they did get stuck when I leaned back by accident and ripped the bottom point off)
If you are either a relatively experienced stiletto girl or you're willing to go the extra mile, then go with your heart!

On a side note, YSL shoes in general are not for the weak of heart or feet. I have bought pairs that felt great in store only to be limping in them after wearing them for half a day. I also have slim/narrow feet and tend to fit in most YSL heels/shoes in general but even then, I have to break them in or get used to them.

As a lover of YSL shoes, do you happen to own any boots in lambskin? I decided to go with the block heel after all as the squared toes grew on me and the comfort won me over. I didn’t look too deeply into the leather because I trusted the brand, but I now realize these are lambskin, which seems a rather delicate choice for footwear. My husband already got them for me for Christmas and I am too attached, but would love to know if any of your durable pairs have been in this leather?

I also tried on a calfskin boot from Celine the other day and comparatively, those felt indestructible, but I suppose the buttery softness that feels like the leather will mold to your feet was part of the allure of the Saint Laurent boots.

 

[lill_canele]

As a lover of YSL shoes, do you happen to own any boots in lambskin? I decided to go with the block heel after all as the squared toes grew on me and the comfort won me over. I didn’t look too deeply into the leather because I trusted the brand, but I now realize these are lambskin, which seems a rather delicate choice for footwear. My husband already got them for me for Christmas and I am too attached, but would love to know if any of your durable pairs have been in this leather?

I also tried on a calfskin boot from Celine the other day and comparatively, those felt indestructible, but I suppose the buttery softness that feels like the leather will mold to your feet was part of the allure of the Saint Laurent boots.

I do not have a lambskin pair from YSL but I do have a rounded pointed lambskin pair boot from Hermes.

I initially was afraid of buying lambskin shoes but to be honest they’re not too bad. I’ve had my Hermes for 2 seasons and even went stomping around in the vineyards in Napa Valley with them on. No issues. I too love the buttery softness of the leather and have enjoyed them thoroughly.

My Hermes SA just said not to kick concrete lol. But I do think the main risk with any shoe is being kicked forward and hitting something. I have a pair of CL calfskin pumps and I nicked off a chunk from just one kick after wearing it only a handful of times and it’s not lambskin.

Going back to lambskin boots, again, don’t think they’re super delicate and are probably fine for regular use.
I suppose, to reduce risk, refrain from running and taking large forward steps?
Due to the finer grain, lambskin does show creasing more easily. But that is pretty normal and expected.

 

[anastasiya26]

I do not have a lambskin pair from YSL but I do have a rounded pointed lambskin pair boot from Hermes.

I initially was afraid of buying lambskin shoes but to be honest they’re not too bad. I’ve had my Hermes for 2 seasons and even went stomping around in the vineyards in Napa Valley with them on. No issues. I too love the buttery softness of the leather and have enjoyed them thoroughly.

My Hermes SA just said not to kick concrete lol. But I do think the main risk with any shoe is being kicked forward and hitting something. I have a pair of CL calfskin pumps and I nicked off a chunk from just one kick after wearing it only a handful of times and it’s not lambskin.

Going back to lambskin boots, again, don’t think they’re super delicate and are probably fine for regular use.
I suppose, to reduce risk, refrain from running and taking large forward steps?
Due to the finer grain, lambskin does show creasing more easily. But that is pretty normal and expected.

Thank you so much for the thoughtful answer. I’m glad to hear you’ve had a great experience with the lambskin. I feel emboldened to stomp around in mine soon too!

Which Hermes style do you have? I’ve found myself noticing Hermes boots a lot lately but haven’t tried any in person yet.

 

[lill_canele]

Thank you so much for the thoughtful answer. I’m glad to hear you’ve had a great experience with the lambskin. I feel emboldened to stomp around in mine soon too!

Which Hermes style do you have? I’ve found myself noticing Hermes boots a lot lately but haven’t tried any in person yet.

I have the Saint Germain in the highest heel height. Black with palladium hdw.

They are nice and sleek in a conservative way.
I have found them great for my narrow feet. I usually can’t do most Hermes footwear (mainly sandals) because a lot of designs are too wide.

 

[anastasiya26]

I have the Saint Germain in the highest heel height. Black with palladium hdw.
View attachment 6105670
They are nice and sleek in a conservative way.
I have found them great for my narrow feet. I usually can’t do most Hermes footwear (mainly sandals) because a lot of designs are too wide.

These are gorgeous! This style and the high boot with palladium hdw are the ones I’ve been falling in love with.