I've been making trips to REI and Performance Bike to get the right combination of layers and I think I'm narrowing it down. I purchased a Showers Pass Transit Jacket which seems to be pretty nice. I also purchased a set of leg warmers that on my first day out I think were the best investment I could have made.

I'm now looking for some medium cool/cold weather gloves and most importantly I was wondering how most folks keep their heads warm?

A skull cap under the helmet works well: https://www.amazon.com/gp/product/B00...ilpage_o00_s00.
I also like to use a buff: Amazon.com : Hugger Mugger Buff Headwear, One Size, Black : Sports & Outdoors. I wear the buff like a scarf around my neck and pull it up over my nose and mouth when I need extra warmth.

Skull cap is good, but be sure it covers your ears too.

I don't have to worry about him too much. The worm generally stays there without complaint. It's warm in there.

I don't think I would want to keep my head worm if I had one.

A balaclava or thin stocking cap. A helmet cover can help, too.

If it's really cold, I'll use a balaclava. Otherwise, I use a hate I pull over my ears. A buff works well, too.

Women frequently ask if that's my head worm in my cycling shorts.

Wicking base layer (long sleeve shirt, long underwear). T-shirt and shorts. Nylon sweatpants with fleece liner. Sweatshirt. Canari poly outer shell (only bike-specific piece of clothing I own). If it's cold (<15F), double socks. Balaclava with a skull cap hat. For hands, a thin pair of wool gloves over a pair of leather work gloves down to 20F. Under that, the thin wool gloves with a pair of insulated leather work gloves over them. I've done this down to 5F, with a wind chill of -10F, and not the least bit cold. Don't know how low it would take me but for St Louis, that will get me through the winter no problem.

I purchased the REI fleece lined skull cap. I can't tell you how much of a difference it made riding in cold weather. By just adding the skull cap, my thighs kept warm as well as my core. It's true what your Mom says about losing a lot of heat through your uncovered head. I now have gear where I can ride comfortably down to 37ºF.

I like my balaclava, which I will start using when when it's in the low 50s probably. It helps me cope with the dry winter air much better.

Balaclava, skull cap and headband all store brand from Nashbar. Less than $30 for all three. I can fit any two in combination under my helmet if needed. Windproof. Layered with multi options. Order some other stuff on a "free freight" special that pops up quite frequently.

Also, the helmet cover as mentioned before. With my thinning hair, I use one below about 60---all winter long. Showers Pass. Works great. The SP jacket will serve you well. The only thing you might like is some arm warmers. The cold hits the sleeve and feels chilly...windproof but no insulation.

For really cold weather, I use a neoprene half-mask face balaclava (one that comes up and mostly covers my ears), and an exercise ear-band from target (C9 brand). Usually, even down close to freezing, I still want the top of my helmet uncovered so my head heat can vent though the holes...It's my ears that get cold, and the balaclava plus ear-band gives me 2 layers on the ears.

Down into the 20's, I will add some kind of skull cap to cover the top of my head.

Starting around 40F I'll put on a light cap. Best I've found is the Minus 33 Reversible Shade Beanie, as it's nice and light and it comes down over my ear lobes. Under 20F or so I'll switch to a light balaclava, then around 5F I'll go with a midweight balaclava.

Hands and feet are the most challenging. Around 35 degrees I'll but light wool socks over VBL socks in uninsulated shoes (fat, mtb and commuting I wear Five Ten Free Riders -- this being Minnesota, I tend to retire the road bike November through March) and then I will switch to insulated boots around 20F and user lighter or heavier socks as needed. From 50F to 35F I wear light fleece gloves, switching to midweight windproof at that point down to about 15F-20F. Around 5F the mittens or pogies come out.

Upper body is pretty simple, with light and/or midweight merino under windproof top. Legs are even simpler, with lighter windproof pants 50F to 25F and then the heavier pants down to 5F and long underwear below that.

How cold does it get in HotLanta? For "medium cool/cold weather gloves", I'd wander on down to Home Despot or Lowes or Ace or whatever, and pick up a pair of work gloves. You can probably get safety ones with orange and reflective bits.

Or just keep your eye on the road for a few days, you'll probably find some...

Big fan of these:
MAXIT®

Covers your neck,ears,and face. I get about two winters of daily riding before they get too stretched out.

I biked to work year-round for eight years while living in Hot-Lanta and don't remember it being difficult to stay warm. And that was a more than a quarter century ago, before Global Worming!

Yes, a balaclava or winter skull cap is very helpful for cold rides.

I wear headbands always (to keep sweat out of my eyes), but in the winter switch to the ones that are shaped to cover ears and a little thicker. I like water resistant gloves that are not too bulky. I'm already using arm warmers and will soon be wearing leg warmers. When it gets colder yet I will wear a long sleeve jersey over arm warmers and finally two long sleeve jerseys over arm warmers. Oh and booties just for warmth. That's barely adequate for 20 mile commute in mid to upper 30s- typical "colder" commute in PNW. No tights, and no jacket but sometimes wish I had one. Or maybe a rain cape.

Your post doesn't mention where you live. It makes a big difference.

I live in Minnesota. Leg warmers are next to useless as a niche item. Far better off to just get full length windproof pants or tights, and wear smartwool under them. Leg and arm warmers seem to have a rather narrow range of improving comfort.

For "warmer" day (above 15F) I wear a goretex helmet cover and a headband to cover the ears.

When it's colder a wear a full on windproof Balaclava, similar to this one:
https://www.eriksbikeshop.com/Bellwe...3E6495/Product

I'm not usually biking in severely cold weather, if I was I could put ski goggles over that and have no exposed skin at all.

A helmet cover and headband over the ears has worked for me in less extreme weather though.

While skull caps and ear bands are good, when it gets really cold I switch to a snowboard helmet with ear warmers and no ventilation holes.

I get too hot when my head is covered with more than a helmet. I make sure I keep my ears and nose covered with a neck gaiter but let my head do with a helmet.

Marc

I let the Head Worm fend for Itself..

Another Minnesotan chiming in: Yeah, "cold" is relative. I'm good without a head cover down to maybe 35F depending on wind. Below that, I switch to a hooded windbreaker and wear the hood under the helmet. Below 5F, I add a thin wool beanie. Below -10F, I seem to have lost interest over the years.

like many people said it is all relative. I am not riding in MN cold. Atlanta should be more moderate you have to figure out if you are a cold or warm person.

You have to experiment at different temps to find what works and what doesn't. I started making a chart and put some different temperatures down the side of a piece of paper and then I would list what I wore. If I could kind of remember if it was comfortable and worked. If it didn't I would think about what I could add or subtract to make it more comfortable. It was great if I saw that is was 45F then it meant I wore this, this, and this but if it was colder or warmer I knew how to adjust. Problem is I lost that piece of paper so this fall I have had to restart remembering what I wore at what temperature.

I have a thin fleece balaclava I bought for $4 from Sierra trading post and it works well in cool weather. It is not windproof though. I bought a had with windproof material around the forehead and ears and it is really warm. I also bought a cheap six six one Dirt lid for winter riding and the lack of holes in the helmet really helps.

As to gloves I bought some windproof ones from Aerotech Designs. I have enough room to put either thin softshell gloves or even wool gloves underneath. It is a good system. I like two pair of gloves. The nice thing is if you get warm you can take one layer off.

I layer up with whatever I find on clearance racks/website sales, in my size of course. From 40-50 I wear a Pearl Izumi barrier elite shell with nothing underneath, and some neoprene Brooks running gloves. Below that I use a wool/synthetic blend base layer with a wind/waterproof outer Cannondale jacket, this generally gets me through to around -5f.

For pants I wear Polartech tights over my bibs/shorts. Around 0 I'll also throw on a set of skivs so the Johnson doesn't freeze. For socks I use wool/synthetic blend work boot socks with Louis Garneau neo protect booties.

My hands tend to suffer the most...I've tried multiple layers with leather on the top but the coldest winds still give me rewarming pains. I've noticed that the dude who makes Bar Mitts makes them for bullhorns now, so that is what I'm doing this winter.

Skull cap under the helmet, generally nothing covering the nose/mouth. It's always amusing to find ice chunks in the beard after a ride.