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Urgent Decision-Making Help Required!

Walking 8-10 miles would not be as comfortable in the third.

They don't look that worse than Cowboy boots arch-wise and I can walk in those forever. Plus the third ones do have some good grip and think soles, protecting them a bit more from accidental scuffs.
 
Walking 8-10 miles would not be as comfortable in the third.

They don't look that worse than Cowboy boots arch-wise and I can walk in those forever. Plus the third ones do have some good grip and think soles, protecting them a bit more from accidental scuffs.

When it comes to walking, I always check the top back part that touches the back of your leg. The point behind your ankles. Shoes that are very thin in this spot always cut my skin, even after only a day of not even constant walking around. Unfortunately all three of these pairs appear to be equally thin in this area.

Another thing to consider - the third will elongate your legs, if you think your legs are stumpy. :techman:
 
I went to catholic school. Saddle shoes suck for walking. They have no tread whatsoever, so keep that in mind.

I kind of hate the last pair, but I think you could use either a bit of a heel or more bulk with that outfit. How about the good old Doc Marten style?
 
I'm not really a fan of the first. The second has a nice clean look, but, yeah, as others pointed out, they'll get dirty and then they won't look as cool.

Third one has a nice quirky look that you could probably pull off if you wanted to.
 
The third pair would probably look better on you, but they do look kinda seventies and may draw attention to themselves. The first pair would present you as a complete classic package.
 
^Actually looking at them more closely, they really are just normal chunky heels. In fact, I'm wearing a pair just like them only all black with a more rounded toe. I think they're just photographed from a bad angle.

In other words, go for the 3rd pair.
 
Does anyone know if Captcalhoun is a serial killer or not? Because I suddenly think this information is relevant.

you've never heard that before? the idea of sticking a woman in a bin-liner dress and her still looking gorgeous?

it's a British idiom.

i would never kill TSQ.

Hermiod and Philo, on the other hand...:evil:
 
The third pair would go best with your plum dress outfit out of those three, by far.

(a heeled black/white wingtip spectator oxford shoe though, that would be just PERFECT for it. I think Brooks Brothers had something like that in their ladies range last year.)

Overall, saddle shoes rarely "do it" for me though, so my advice is of limited value due to that bias. Having said that, if you're going to do them, the top pair is probably the most aesthetically "balanced" I would say.
 
When in doubt go classic (Option #1). For your plum outfit black knee-high boots would be the way to go, imo.
 
The third pair would go best with your plum dress outfit out of those three, by far.
That's for sure, I wouldn't even consider wearing that outfit with flats.
(a heeled black/white wingtip spectator oxford shoe though, that would be just PERFECT for it. I think Brooks Brothers had something like that in their ladies range last year.)

Overall, saddle shoes rarely "do it" for me though, so my advice is of limited value due to that bias. Having said that, if you're going to do them, the top pair is probably the most aesthetically "balanced" I would say.
I went to catholic school. Saddle shoes suck for walking. They have no tread whatsoever, so keep that in mind.

I kind of hate the last pair, but I think you could use either a bit of a heel or more bulk with that outfit. How about the good old Doc Marten style?
I can appreciate wingtips, but I've always felt that they're a bit masculine for me. I have a soft spot for saddle shoes. When I was a kid I wouldn't wear anything but saddle shoes for about 5 years (funnily enough, until I got my first Docs -- classic black boots with hot pink laces -- at age 10). I think I may have to give in and buy both. One now, and one with my next paycheck. But which to buy first?

Everyone has been such a great help so far, thank you!

As for knee boots, I wish. I can't fit in anything but ankle boots; my calf muscles are huge. It's irksome, really; I'm a size 2-4, at most I'm 10 lbs overweight, and yet if I want boots I have to buy them plus size online.
 
The third pair would go best with your plum dress outfit out of those three, by far.
That's for sure, I wouldn't even consider wearing that outfit with flats.
(a heeled black/white wingtip spectator oxford shoe though, that would be just PERFECT for it. I think Brooks Brothers had something like that in their ladies range last year.)...

I can appreciate wingtips, but I've always felt that they're a bit masculine for me.

I found the Brooks Brothers shoes I was thinking of. But in my mind, I had merged that colour scheme with THESE ones, and that combination would have been perfect.

(the current sale price on those latter ones is superb, by the way.)

I don't think wingtips are necessarily too masculine, when the rest of the outfit is so feminine. Worn with a trouser suit; or in a more clunky last, yes they can be, of course.
 
Thanks everyone for your help! I have decided to buy the top pair first, because they are so classic and versatile, and to buy the bottom pair in two weeks when I get my next paycheck.

Holdy, those wingtips were oh, so droolworthy. I actually gasped when the image first appeared on my screen! Alas! They are far out of the price range one can afford on a teacher's salary. :(

You want to buy them for me, don't you? Don't you? ;)
 
I didn't even see this! I'm glad you decided on the first. That would have been my choice. :)
 
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