BMX style platform pedals, wool socks, plastic bag over the socks, and my warmest shoes - usually trail runners or light hiking boots.

Much warmer than anything I tried with any cycling shoes with cleats, including neoprene booties.

Get some good boots and ditch the plastic bags, it'll be worth the money. If you only ride your bike in boots like I posted above they'll last for a good 10 years easy. The more time you walk in 'em the shorter their lifespan.

Sandals with 0 to 3 pairs of wool socks depending on the temperature. I wear large socks, so the outer layer is XL to keep from getting too tight. The sandals adjust with Velcro in three places to allow them to fit just right no matter how many layers. If 3 layers is not enough, then a windproof shoe cover over it all.

And waterproof socks for when it is too cold to get wet.

Very versatile, allowing for a cold ride in and a warmer ride home.

The solution you use depends on how long you're riding and how cold it gets. For example, I can wear my regular road shoes and two pairs of socks at 35F for 30 minutes. But at the 25 minute mark I can feel the bitter cold on my toes. Riding for an hour in the same conditions would be unpleasant.

I'd tried everything years ago (not cycling back then, walking still had my feet freezing in <30 F). Then I got a hand-me-down of a small pair of men's tall rubber boots. Being too big for me, I wore them with a thick pair of wool socks with thin socks underneath, and voila' -- no more cold feet. At one point I was out taking pictures and went and stood in the water of the Chesapeake Bay after a snowstorm in January and didn't feel the cold water at all. A few years later I started wearing Crocs at work, and noticed that my feet stayed warm with no socks at all until it was absolutely freezing out; even then it was because of exposed skin at the back. Thick rubber or rubber-type material blocks the wind and really insulates my feet from cold air better than anything else I've tried.

i got a pair of -40 hiking boots, and with a thin pair of socks, work perfectly for my cold commutes. i have to make sure that my pants legs are secured over the boot to prevent any gaps, but my toes and feet keep toasty warm.

this year I have discovered, embrocations.

specifically I am using Northwest KneeWarmers https://northwestkneewarmers.com/
I have 3 different strengths.
in my opinion its pretty amazing stuff.
I ride about 200 miles a week, I ride before and after work, thru out the week, nights, early early mornings, in the rain, etc...

rub this stuff into your legs, into you feet, etc...
honestly, fairly awesome stuff. I've put on my arms some too...

I haven't been cold yet, and I swear... my legs feel better, and I'm able to spin better, and focus more on the quality of my rides.

thin sock liner, thin chemical toe warmer on top of toes not under, outer sock of your choice. when u get to work put the toe warmer in an air tight bag and u can use them on the ridr home too

asana: so it just keeps you warm?

Neoprene booties. Lycra booties will help some, but nothing beats neoprene. You can still use your clipless pedal and walk as normally as you currently do in whatever shoes you use, but cold and wet are severly limited. So much so in fact that I am looking for neoprene-backed gloves.

Tip: In really cold weather you can drop one of the hand warmer packs in the toe area of your shoe as well. They seem to work well for an hour or so.

sheepskin insoles and toe covers.... at least down to 35 , I will not ride in any colder than that.

I actually use two Gator products. These are their neoprene road booties (they also make a mtb version):
https://www.gatorgear.biz/robode.html

And these are their neoprene socks:
https://www.gatorgear.biz/basicsocks.html

The booties are for most extreme conditions and the socks work great in the rain, or you can wear both when it is REALLY cold.

When I lived and rode in a cold climate, I used LAKE winter cycling boots, a size large, and heavy wool hiking socks under them. Worked down to about 0F.

I'm still getting use to using the stuff.
when it gets wet, it heats up even more than usual.
from what i can tell, there are a variety of "embrocations" out there.

basically, the idea is to enhance blood flow.

clothing holds the heat in.

i guess you could say, embrocations speed up the heat.

in the years past I've been really cold. when I was in the army I had been in the field a lot, wet, etc... so my hands and feet were subject to be cold/waxy/pasty like (i.e. frost bite)

however, over a decade later, I don't get very cold any more.

with embrocations, I have now have 3 different strengths from Northwest knee warmers.
I will say, that I do end up spending some time stretching, warming up, then rubbing the stuff into my legs.
now days, when I get on the bike, I'm already somewhat warmed up, compared to years past, I'd just hop on the bike and go.
I still do that some too, just not that often.

yesterday I rubbed down, and rode for about 2hrs before work, ending my ride at work...
old trick, right? get my ride in before work.

I was riding in Pebble Beach, when it started to drizzle. I ended up riding for at least an hour in the rain.
funny thing with me and rain, especially when the rain comes about 1/2 way into the ride.

so I'm riding, and the heat from the embrocation is increasing
by the time I get to work, I'm pretty wet. wipe down, and change clothes.
interestingly, its like a film of sorts.
I wipe down with baby wipes
and the areas where I have applied the embrocation, I just use wet paper towels, wiping straight down the legs.
its great, I'm all gritty with road grime, and it all just wipes off.

I drink down a bottle of Recoverite, and I start my shift.
for awhile into my shift, my legs are still warm/hot as the embrocation is still activated.

My commute is six miles each way. In that distance, my feet stay warm enough no matter how cold it is (my fingers are another story). If I ride longer, as I do on the weekends, my toes freeze despite wool socks, shoe covers, etc. I am convinced that short of chemical warmers, as mentioned in earlier posts, there is nothing that I can do to keep my toes warm. Question- what chemical warmers are good for feet and where do you get them?

Am perfectly comfortable at 28 f with cycling sandals......1 pair of merino wool socks...and sealskin socks, key being the sealskins

Chefisaac: From your post, I presume you're using platform style pedals (i.e. no cleats)? If so, I'd think you probably just need larger boots/shoes and thicker/more layers of socks.

The challenge for me was using my clipless as the temps dip below 30F -- I find the cleat/pedal act as a major heat suck. My solution was larger shoes with thicker insoles. Where I used to have toe numbness in 1/2 hour or so, I can now go an hour or more without my toes suffering too badly. You might consider whether your shoes (and soles) are 'thick' enough (and not too ventilated) as airflow will rob you of heat. likewise, not all wool socks are equal; thin wool (or silk) socks are intended (generally) as an under-layer or liner sock, to be used with a thicker loft/insulation layer when the temps drop.

what kind of shoes? Are they room temperature when you put them on? I rode for 12miles in these during cold rainy weather and snow and they were great. Goretex socks over medium weight wool socks have helped a lot in my cycling shoes that have lots of room in them.

With due respect, I don't think the concern is with 28 f. Toes and fingers can be kept easily warm at that temperature. When extremities are exposed to temps below 15 f, that's when toes and fingers become a concern.

Yesterday, 28F:

+ +

Shimano MT21 + thin cycling socks + wool hiking socks = toasty warm feet

Today, 30F:

+

Shimano MT21 + wool hiking socks = cold feet

I wore the cycling socks yesterday as a fungus barrier, since none of my wool socks were clean. I'm shocked how much difference they made.

As to what constitutes "cold" I think it depends on the climate in which you live. I grew up in the hills of western Maryland and I had no problem going out in sub-zero temperatures. After 15 years living in the PNW, anything below 32 is quite cold. Your body adapts, I guess. Or maybe I'm just getting old.

I am clipless. I would like to avoid platforms for right now. I love my clipless system.

I don't know if this applies, but I use Sidi's and SPD's, so I use silicone to seal up the slots where the cleats attach. I always thought it was lame that I could walk on wet grass, and have water seep into my socks. lame. so when I install my cleats, I use blue lock tite on the cleat bolts, and silicone the cleats and fill the adjustment slots.

Dump the silly bike shoes if you are wearing them. Any pair of decent work or hiking boots will be warming with a nice pair of wool socks.

me too. I find it pretty easy to stay warm with regular winter boots and thick wool socks, but to go clipless this is what works for me:

Lake winter boots
VERY THIN wool socks (liners, really)
and a pair of toe covers -- not full booties, just the ones that cover the toes - over my SOCKS. (https://www.sugoi.com/usa/resistor-toe-cover-1.html)

works quite well.