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Should I get some more dresses, skirts and boots/flats??

I really like wearing dresses and skirts and with the weather is getting warmer I have more chance to :smile: I wore this short flowery dress with some brown boots today and I felt comfortable in this style. I have a couple of skirts and dresses that I can wear casually in the day already but was wondering what to do about buying some more. I figure I will be able to wear them quite often in the next 3 months or so but once it gets to September it will be too cold to carry on wearing them... Will I be able to wear most of them with tights or leggings in the winter? Would it look silly with a coat? I really don't know... I don't want to but loads of clothes that I can only wear for one season D: but I do want to start wearing more skirts and dresses!!

Another problem I have is shoes... Flat shoes almost always really hurt my feet and give me blisters/make them bleed :frown: is there a way of preventing this?? I have a pair of boots that I have been wearing but I don't think they will go with EVERY skirt/dress and I can't just wear them all the time anyways..
I only ever really wear dresses and just wear the same dress without tights in the summer and with tights in the winter. It really just depends on the type of dress. If you are buying knee length and shorter than it should be fine to wear with tights and a cardigan/coat in the winter. However obviously longer dresses like maxi dresses you can only wear for a certain type of weather :redface:

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