Unlike previous winters, I actually HAVE to do my long run (on the treadmill, no way) because of that May thirteener I have coming up, so I need to get over my extreme aversion to the cold and just get it done. Over the years I have bought various things to help me with that. Some have worked, some have not.
Right now what's working for me is:
Warm leggings from Target (maybe these?) that I got on sale for less than $15. If they had more than one in my size I would have gotten them all. They are warm and comfortable and I don't have to wear anything else (I have not run in negative temps with them but I don't plan to. I have limits.)
I recently bought a thicker pair of Injinji socks. I will only run in Injinji socks. Before I bought the thicker pairs my toes were freezing. I doubled up one day and that worked out well. But the mid grade ones seem to be working ok on their own. I run in minimalist shoes which are great but don't have a lot of extra material to keep my delicate toes toasty.
My mom got me the base layer shirts from Target to wear underneath my running shirts. I've one that is a smooth dry wicking material and one that is fleece. They both work well but I save the fleece for really cold temps. I have thicker running shirts as well, but I've found that when it's really cold I'd rather layer. So I wear the base layer, a thinner long sleeve running shirt and then a jacket that I got from, you guessed it, Target. This has been working for me this winter.
I used to run in gloves and my fingers would freeze. But I don't like mittens because I have less control over my fingers and I often have to blow my nose. So I compromised with these gloves. I can wear them as mittens or pop the top off and expose my fingers. They are really warm.
The highlight is the face mask I just bought (Amazon). I LOVE it. It has a ponytail spot for extra lovability. Even while wearing a hat my forehead would get cold, my cheeks, my nose. If I focus too much on my face hurting I don't focus enough on running. With the face mask my head and cheeks are protected and I can choose to cover my mouth and nose, or just my mouth, or nothing. I have yet to find a satisfactory solution to fogging sunglasses (that I wear to protect against wind or sun) so I sometimes cover my nose and sometimes don't. If it's super cold I'll wear a hat too, but the face mask is enough in regular cold.
I've always been interested in yaktrax but they're pretty expensive and I'm not sure how well they would work with my minimalist Merrel's. So when I saw these in the grocery store--that's right--for a wicked cheap price I figured why not. I haven't used them yet but they fit on my shoes. I'll let you know if they're cheap crap or actually worth it.
I ran in 6 degrees a couple of weeks ago and while it was cold, I didn't die. I can't say I was warm but I was able to do 6 miles mostly because of all this stuff. I never use to run if it was below freezing before, so this is a pretty big step for me.
When I run in the treadmill I wear capris and short sleeves but changing into them and out of my warm winter wear is often the biggest hurdle to my weekly running. So this winter I have done something different and not changed. When I get dressed in the morning I put on my exercise clothes, whether it be for running, biking or crosstraining, and then my "day clothes." When it's time to exercise, I just have to take my outer clothes off, put on my Injinji socks and shoes, and I'm good to go. This has the added benefit of acting like long johns or thermals so I'm not as cold during the day. Boom.
I'm finishing up my biking right now and I will diffuse some Citrus Bliss later today. It'll take the sting away, but I'll still be dreaming of summer tonight.