Right around this time of year, every year, why is it that I find I look old, tired and fat*? And it's always when it's tax time too.

Ugh.

In the spirit of trying to enjoy the rest of the winter, and to dress for the life I actually have, I am asking for your help in determining which boots to keep or what coat would go well with them.

We are just exiting a 2 month period of intense cold, where only boots in pic 1 could be worn. So now I want to wear the other ones... but what types of coat or warm jacket goes with which?

PICS 1-2-3
My favorite ones, bought last fall, it was a very smart purchase. It was my first time with lace-up faux-fur boots and yes. This is what you need here in deep winter. Period. I have been wearing them every day for the past 2-3 months and strangely, I'm not tired of them yet. They "make sense" with many ski-jackets type coats which is very handy.

PICS 4-5
My second favorite ones, from Blondo. But they are not as full proof as the first pair. Yet, can be worn in the city during our winters. They are a good alternative to black. I recommend anyone to get this shade, as it goes well with denim, thick tights and many other winter clothes. Yet I can't really wear them with ski jackets.

PICS 6-7
I almost did not touch these this year, when they were a workhorse for the past two winters. That's because they fit so well on the calf. But... even though they are waterproof and supposed to keep feet insulated under -10, my toes tend to freeze if I wear them in temperatures lower than -5.

PICS 8-9
I am rediscovering these El Naturalista turquoise mid-calf boots, and also the tucked-in look with roomier bootcuts. I've had them for 3-4 years now and always have struggled to match them with an appropriate coat. This one from Talbots bought on sale last year now looks okay in the pic, which makes me realize that maybe I should have paired them with preppier outfits instead of the boho vibe I was trying to tap into. What do you think?

PICS 10-11
Another El Naturalista pair. I thought I was making a sensitive, intelligent, no-nonsense - albeit pretty expensive - choice when I purchased these. Then I seldom wore them, and each time I did two things happened: random people stopped to compliment me and I couldn't wait to run home and take them off. So... since I won't have it that the problem is in my head, I think it might simply be because they don't go well with the rest of my winter get-ups. Pic 16 is how I think they should be worn but... this is so not me! Yet I'm giving them one last chance. Any suggestion?

PICS 12-13
Knee high cognac Blondos I NEVER wear. What s wrong with them? I don't know. I can't figure it out. Help!

PICS 14-15
These Rockport looked so badass I couldn't resist. Except... I am struggling with them. Maybe I just don't own the appopriate topper. In 15, a between-season jacket I think would do. But it only makes me half happy. Any ideas?

Thank you for looking and helping me!

*By this I mean how I feel inside. Not how it really is. I'm changing decades this year. All the old fears are bubbling up at times, especially if I'm vulnerable. Also, trying on coats and boots is not my favorite. But it's necessary.