I have gotten the outerwear thing dead wrong for horseback riding/being at the barn every winter since I was a kid. I have worn various types of layers - usually a long-sleeve shirt, a fleece jacket, and a down vest - for the past few years. Before that I wore a normal winter jacket. The layers never seem to work out quite right for the really bitter cold days. I have low blood pressure and Reynaud's Syndrome (causes fingers to turn blue) so I definitely keep my fingers and toes warm, but that even with the layers is often not enough for Chicago winters. 

I would invest in a set of silk long underwear. I know it sounds ridiculous, but it really helps you to stay warm! Trust me, I used to stand outside (well, in the indoor arena, which was maybe 1 degree warmer than oustide) for hours and hours when I taught lessons up in Chicago! They also make silk sock and glove liners. It's great because it's super-thin, yet really helps keep you warm.

I also always made sure that I wore a wool sweater. Yes, they're itchy, but ya won't feel it if it's on top of the silk long underwear. Wool socks are a must, as well. Also, I never bought any (especially once they got so popular), but I once had a lady tell me that I should buy a pair of Uggs. She said they really keep your feet nice and toasty. I always just used those little warm-up packets that you stick in your shoes. :-)

For really cold days, I had a pair of flannel-lined jeans. I think I bought them from LL Bean or Land's End. They were certainly not cute, but they were warm! With the silk long underwear underneath, they did a good job of keeping a lot of the chill away. Down jackets are great, too. I used to have one that wasn't super-puffy, so I could still ride in it.

 Hhhhmmmm,I can't think of anything else. I've been down here in Miami for too long! We are currently experiencing a "cold snap" -- as in, it was in the lower seventies/upper sixties during the day and the low will be in the mid-to-high fifties tonight. One of the girls at the barn was wearing a hoodie (with hood up) and gloves and complaining about the cold! Lol. I was wearing a short sleeve shirt and thought it was perfect!

 

Oh, I also used to have a really nice set of cashmere-lined gloves that, surprisingly, kept my hands pretty warm. And I'm fairly sure my upper layers used to go: silk long underwear, wool sweater, turtleneck, sweatshirt, fleece vest, jacket. Yes, that is a lot, but I was standing around, not riding! I think I actually would sometimes wear more than one sweatshirt, as well...yup, pretty much a walking Stay-Puff marshmallow. If you're riding, obviously, you don't need quite as many layers.

The silk long underwear (mine is skiwear) are perfect.  On a really cold day, I will put thermal ski underwear over the silk ones.  Then the pants, a turtleneck and jacket over that.

My dh bought me a really nice Carhartt riding jacket that is some sort of microfibre.  Very nice and warm.  I also wear ski bands to cover my ears. 

I will try the wool socks, Frizzle.  My toes always get cold,LOL.

My sweet husband just bought me some Muck Boots from TSC yesterday.My horsie family members all have some and they're comfortable and keep your feet nice and warm.TSC also had flannel lined jeans someone said they are very warm,i'v never tried them.

 

 Layers, layers, layers.

 

To start: Hot Chillies long underwear.  It is designed for skiing and costs a arm and a leg, but I get mine for Christmas!  I get the bottoms that have the foot loops, so I can pull multiple layers up over that without them getting all wrinkled.  Then I do Smartwool socks, usually the knee high ones (I recycle a lot of my ski clothing this way!), WINTER BREECHES!!!  They are a gift from the gods.  I have a pair of fleece ones that keep me toasty warm.  However, if Jackson starts shedding, I begin to go from black breeches to white hairy ones.  If I'm riding, I wear my mountain horse winter boots, sometimes with another pair of wool socks over the breeches, depending on the temperature.  I also know someone who has a pair of Mountain horse snow pants, they are lined snow pants but have patches on them like breeches!  She loves them and has had them for years (the same pair).

 For the top:  Once again start with Hot Chillies, then a long sleeve t-shirt.  Then a sweater or sweatshirt - I have a few sweatshirts that are deemed for-barn-use-only, then a down vest and very last, a soft shell.  I find a soft shell is warm enough if you have all of those layers, plus, they are really good at blocking wind and snow.  Plus, nothing sticks to a softshell, making it perfect for barn use.  

This is my system, tested through quite a few Maine winters.  We don't ride if it is under 15 degrees, so I've never tested it in truely cold temperatures.  I also use winter riding gloves with those little strechy gloves under them.  I've heard that silk is the best liner, but I'm to cheap to buy them.  Maybe if I get them for Christmas... hmmmm.  I also have the problem with my feet and hands getting cold.  Usually I warm my horse up by hand walking it and sometimes even trotting if I feel up to it, and cool down by handwalking as well.  That gets your blood moving a little bit more and helps to keep hands and feet from falling off.  What really gets me is the tacking up and untacking.  That's when my hands usually turn into ice cubes. 

I agree - silk long underwear is the best and it's not bulky so you can still pull riding boots on.  I also LOVE Thinsulate -- in gloves, boots, jackets...it always keeps me warm even in biting wind.  I got a pair of Thinsulate SSG gloves last year and that made a huge difference.

I picked up a pair of Kerritts fleece lined breeches last year and now love them more than life itself, worth every penny, feel like sweatpants, but much warmer than regular breeches and so comfy.

You need a good outer shell for wind too -- I would look at sites like Sierra Trading Post (can't beat their deals) or Campmor for good outerwear jackets.  My barn jacket is a ten year old LLBean (their stuff NEVER wears out) with fleece on the body and Thinsulate in the sleeves and water resistant outside.  It's so dirty and bright yellow but I don't care because it's always warm and indestructible.  The most important part is for it to BLOCK WIND.

I'm also investing in a pair of Mtn Horse winter riding boots this year, I'm tired of having ice block toes....

You don't have to wear a million layers if you pick the right ones -- I usually go with one shirt next to skin (your silk), then a midlayer of fleece, then jacket outerlayer.  If it's REALLY cold, like 20, I'll put another shirt between the silk and the fleece.

 This is great, I need winter boots and breeches myself. Solaris, can you give me an idea of how much those Kerrits cost? And tell me more about the Mountain Horse boots - a friend let me try on hers last weekend. They were a size 10 and I take a 9, but the foot fit perfectly, but the calf was too big. They seemed fine to ride in, but I've had problems in the past keeping my toes warm so am very leery about that. 

 I'm asking for silk long johns for Christmas. They're actually not that expensive at L. L. Bean's.

Flakemusic, I noticed you said you had Reynaud's, and I know that is a big problem in the cold. I don't have it but am a sissy about the cold, and what keeps my hands warmest is to wear a pair of thin gloves under a pair of mittens. This is at least as warm as the thick ski-type mittens and allows your hands to be a little more flexible/useful. My hands are hard to fit, especially in gloves, so I usually end up buying a women's large and then cutting off the ends of the smallest fingers and restitching them. Obviously you can't really ride in the mittens, but you know there are "riding mittens," although I've never tried them. My hands usually warm up once I get riding, but if yours don't, you could also have in your pocket a pair of slightly heavier wool gloves. I inherited a pair of those from my daughter when she moved to Utah, and it's surprising how warm they are.

I have the flannel-lined jeans from Bean's, and I have to say, they're only good down to about 35-40, and I can't imagine riding in them, the seam would be way too bulky. I ride in sweat pants a lot in the winter, sweat pants over my riding tights. On the coldest days I wear the puffy ski pants over the tights, but that's less than satisfactory (too bulky). My instructor just got a pair of puffy riding pants, though, and she loves them and says they're not too bulky, and she's one that would object if they were. Wish I could remember the brand name. They weren't cheap, but for a one-time purchase they'd probably be worth it.

Edited to add, the gloves I'm talking about are not riding gloves. I've never yet found a pair of riding gloves that fits me just right at any weight. 

I think the breeches are maybe $60-70?  A lot for me for breeches...I usually get mine off ebay for cheap. 

I haven't bought the boots yet, but I think I'm going to get the IceRider ones.  Two friends have them or similar models and have used them a lot for mountain riding here where it gets quite chilly.  I will have to see which kind I think will fit me best, MtnHorse makes about 5 different winter styles now.

Thanks everyone, this helps a lot! 

thank goodness it rarely gets that cold here!  but there have been a few cold days when I had to ride, and I think the thing that helped me the most was my riding gloves and my headband thing that covers my ears.  otherwise a jacket and a couple of layers underneath (shirts only) were fine, and my regular jeans.

TX, there are no words to describe how jealous I am! Family is all that is keeping me in IL, otherwise I would be getting the heck out of Dodge. 

flakemusic:

TX, there are no words to describe how jealous I am! Family is all that is keeping me in IL, otherwise I would be getting the heck out of Dodge. 

Oh no don't be FM, I'm sure y'all get to ride a lot more in the summer than we do, so it evens out!  Besides, Family is very, very important!

I'll usually wear an Underarmor shirt and a light long-sleeve if I'm doing a lot of active work. I'll wear a hooded sweater over if I need it. For the rest, I just throw on a snowboarding style coat. They're lightweight, and aren't too warm if you're moving around a little bit and usually have elastics at the wrists and an elastic belt at the waist to keep the cold air (and snow) from running up inside your coat.

 

FM, 

Back in the day when I was paid to be out in the cold on horseback , part of our winter riding uniform was a pair of suede chaps (we got ours from Libertyville SS and rather inexpensive). With the right layering, these suckers were toasty, and blocked the wind, and it didn't hurt that you had the extra "stick"! I also had those winter riding pants which were more like snowmobile pants with knee patches which were not so forgiving in the hip area!