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As we are entering the cooler temps of October (we had a pretty mild start the first two weeks with 20 degrees during the day) it gets a bit trickier to wear dresses without feeling cold but to be honest I am up for the challenge cause I still am not a huge fan of pants (at least not until I have lost the last pounds of baby weight).
Tights are a huge part of wearing dresses and skirts in German Fall and Winter seasons cause it will get quite cold so I´d say go and find a pair you really like and get a couple of them cause you will need them. My favorite pair of black tights (my most used color) is a 40 den opaque sheer black tight. And I always size up a size cause I can not stand a too tight pair of tights and also hate if they are too short and you feel like loosing them while walking.
Another piece of clothing you will dearly need are boots. Doesn´t matter if you want to have riding boots, lug boots or western boots (I just wouldn´t go with Uggs, cause they will look very bulky with midi or maxi dresses).
And last but not least you can never go wrong with some sort of cozy jacket like a vest or a cardigan.
It is cold in the Winter where you live ?
