well we definitly get cold weather here! And for Layla winter is HER season... she just gets so hot in the summer and she LOVES sniffing around in the winter!  she does not wear booties... we tried... she kicks them off.... she always wears a sweater and a jacket at the same time. I know Old Navy has sweaters with holes for the D-ring. We get sweater from Sonja at Pocomutt and if you ask her she makes a hole for a d ring. Layla has a jacket from Petedge that has a hole but her other one doesn't.. but it's no biggy.. we just attach the leash and it sticks out the top.
We still go for long walks eveyr night even when it is snowing.. Layla comes... we bundle her up and she walks until she tells us she has had enough (usually digs her heels in) and then we will pick her up and put her in our coat. This year we have a backpack for her. we will heat up her heating disk and bring it with us to put in the backpack for when she needs a break. let your pups tell you when they have had enough. you would NEVER guess a yorkie would be a winter dog but they can be as long as you dress appropriately