Honesty, I don't have any winter clothes. Therefore, the only way to survive a 50 degree weather is to layer for warmth.
Here's what you need to know to be a layering expert.
1. Invest in a warm vest. You can layer that with long sleeve sweaters, shirts, or knits. It's flattering and your arms can breath! I hate wearing bulky coats that gives me a hard time moving around.
2. Leather jacket is your best friend on windy days. It's versatile and they go with everything. I love wearing a longer shirt inside to give it an edgy look. I would usually feel warm with 1 layer under the jacket (minus the cami). However, if it's a really cool day, I'll layer a short sleeve under a flannel and put on the leather jacket.
3. I love oversize pullover sweaters because they're so comfortable. Since there's so much free space I usually wear light button down shirt (I love showing the collar of shirts) when I want extra warmth. If it's super windy I'll throw on a scarf.