We went out to dinner on Valentine's with another couple (former clients of DH, not romantic AT all!) Anyway, I wore a black pant suit I bought last summer and haven't worn and a pair of round-toed shoes I bought last fall and never wore before.
Well, it just didn't seem right. I didn't have time to change shoes, so I wore them, but it looked wrong.
Are there general guides as to when to wear round vs. pointy toed shoes? Round for skirts? Pointy for pants, or just some pants?
I don't think there are any rules, it's based on personal preference. I personally like the look of pointed toes on me. However, other girls look great in round toes, but it wouldn't feel "right" on me.
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Veni, Vedi, Visa.
I came, I saw, I did a little shopping.
I have experienced this same issue. I personally prefer pointy toes, but sometimes a round-toe shoe will captivate me enough to buy it. I do find that with a wider-leg pant, I feel like I need a pointy toe to balance out the pants; round toes seem to get a bit "lost" under all the width. Boot cuts don't seem to pose that same problem, but a wider (all the way down the leg) trouser style does.
Round toes seem more retro looking to me, and pointy toes more modern, so I try to put the right shoe with the right skirt. I think a more feminine suit or skirt (flirty details, as opposed to a plain-cut suit) can take round toes better.
Other than that, I can't think of any guidelines I try to follow with round toes. I usually will just look at the overall outfit and go with what feels right, just as you mentioned that the shoes "seemed" wrong to you. I think it's more intuition-based than anything.
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"Good taste shouldn't have to cost anything extra." - Mickey Drexler
I think round toes can look really weird with flared or wide-legged pants. I like wearing them with straighter-legged pants or ones with a slight bootcut.
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"We live in an age where unnecessary things are our only necessities." --Oscar Wilde
I think Pointy toed shoes work best in general with trousers, pants, jeans etc (and mine are all bootcut). Round-toe shoes seem to go much better with skirts, dresses, a little more feminine. The round toe shoes make my feet look smaller so they can get swallowed by pants - and the pointy toes do just the trick under a good bootcut trouser.