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Yeh I kind of think if it feels ok for me I should just do it but with me there is always an element of what will other people think....one day I will grow up and stop worrying about all that and wear ridiculously flambouyant outfits that are decades out of date and be eccentric !!
I don't care if it is dated or not,I like wrap or tunic style dresses over jeans for an informal look or linen trousers for a smarter look.Great way of getting more mileage out of dresses that may feel too smart for day to day wear too.Go for it!