Mid 20's to upper 30's you can get by with a good winter wool sock (Wigwarm, REI's own brand, etc), and a plastic storage bag covering the toe/forefoot (ordinary grocery store bought zip lock style storage bag - without the zip lock. Just buy the cheap ones). Then put your cycling shoe on and go riding. You don't need toe covers as that is fulfilled by the storage bag.

If you are going to be out for over 2 or 2 & 1/2 hours, or in colder temps, I would probably get electric socks or heated insoles, and use the storage bag if the socks do not include a wind block layer (some do). Cycling boots are another option, albeit a more expensive option, but I would still get the electric socks or insoles. In fact the electric socks and your normal cycling shoes should do you into the teens.

Skip covers or booties, they are not worth the hassle.
Proper boots are the way to go. 45NRTH makes a great shoulder season boot and it’s not too hard to find them on sale because they do small tweaks each year and retailers dump the “old” models. I bought a pair of Japanthers last year and love them and the new boot is the Ragnarok.

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"When the going gets weird, the weird turn pro."
Hunter S. Thompson

I would echo that but strongly look at the Lake boots instead. I own a pair, and have compared them with friends 45nrth boots. Buy from an actual shoe company and skip the questionable goods QBP churns out.

Depends on WHERE in Michigan you are. If you're in the U.P. for example, Marquette, Houghton, areas where winters are especially harsh off of Lake Superior, Shower Pass socks are waterproof and while sort of thick, can keep that moisture off. Youd need some overboot like the Pearl Booties. The warmest booties I've tried are Performance neoprene--but since they're going out of business you'd have to order asap if they have any left.

If in LOWER Michigan, you may just as well get some battery heated socks and use those, with an overboot, it's considerably warmer on average than the U.P. I speak from experience on both points.

I can't speak specifically to cyclocross, or dedicated winter boots, but this Canadian has used a combination of chemical toe warmers (those ones you stick in your ski boots), saran wrap, and windproof shoe covers with good success on my road bike. Edited to add, nothing beats merino socks to keep your feet warm. Make sure they're thin enough to not restrict the circulation when your shoes are on.

Any shoe cover that fists snug, two hand warmers, place one on each toe, cover with shove covers and toes stay warm the entire ride.

I first bought Pearl Izumi toe covers (cheap) but moved up to full shoe covers this winter (also relatively inexpensive). Those are working great for me, much warmer than the toe covers. I'm sure actual winter riding shoes are awesome, but they're fairly expensive (from what I've gathered). Personally, I don't do enough riding outside in cold temps to justify the cost of winter riding shoes.

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"The first virtue in a soldier is endurance of fatigue; courage is only the second virtue."
- Napoleon Bonaparte

Depends on you and how your body reacts to low temperatures.

As tri-tele said:


That was what I found to be the best answer for anything below about 35 degrees. I use toe covers for most rides below 50, full shoe covers between near mid-40's to mid 30's, then the winter boots (I have Shimano boots) come out.

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Since I enjoy MTBing in the winter but am ‘built’ for warmer climates, I bought full shoe covers—Vaude Pallas III. They really help. I can now ride well below freezing without problems.

I think any neoprene shoe cover will help a great deal.

I also tend to wear merino wool socks.

Ciao

I do wool socks until the low 30's then put a neoprene bootie on. But where I live, I don't see anything below 20.

Neoprene booties and a good pair of thick merino socks are my go to. I get cold fingers and feet extremely easily and I’ve never had problems down into the 30s. I’ll toss a windproof “aero” shoe cover over the neoprene in the 20s.

Castelli and Shimano both make good pairs without a zipper which I prefer.

Spatzwear.com

These will keep your feet and lower legs plenty warm.

+1 to socks, then bag / seran wrap, then shoes. The toe covers don’t do much at all. Similarly, for your upper body, cycling jersey, grocery bag on your torso, then jacket. Don’t knock it till you try it.

I’ve been riding for over 30 yrs. I do a fair amount of winter riding in a Connecticut. More so now that I have proper footwear. I have probably owned 12-15 pairs of booties in my life. I have used chemical warmers too. All thicknesses of wool socks. I have ridden in double booties, booties plus toe warmers, winter insoles, etc.

This year I got a pair of the Northwave Extreme R/R winter shoes. They are incredible. Not only are they warm but it’s so nice not having to deal with booties. Also there’s no bootie bulk around your ankles which is great. I rode for three hours today in the mid-30’s. Feet were fine. This is with a summer weight wool sock!

I own the Lake CX winter road shoe as well and I find that they are about 10 degrees less capable than the Northwave and more restrictive around the ankle. I use a bootie with this shoe when it’s below 40.

I have a close friend and riding buddie who has owned three pair of winter shoes including two versions of the Sidi. He switched to the Northwave last year and it’s been the best winter shoe in his experience.

Bdaghisallo's post above:

Reminded me of something -- a lot of how cold your feet feel is about how you insulate the blood supply to the feet! If you're wearing thin tights above the shoes, then you're cooling the blood before it even gets to your feet. Protect the lower legs from the wind as well.

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Some are born to move the world to live their fantasies...

https://triomultisport.com/
http://www.mjolnircycles.com/

Thank you everyone, really appreciate all of the insights...hope to "test" some of the feedback this weekend :)

I have some neoprene shoe covers that I use this time of year. I like that I can switch them between my road and mountain bike shoes... keep my feet very warm in single digits to 30s in my experience.

I recently did a mountain bike ride where my shift cables kept freezing on my downtube and BB... even my rear derailleur pulley was getting caked in ice. It was cold, but my feet were fine... double leggings, socks and the neoprene covers.

You've gotten some really good responses. I live in northern Minnesota and ride outside in MN and WI year round. I have a footwear system and clothing system depending on the temperature but also the wind, and whether it's sunny or not. Over 45 degrees F I don't do anything different-my feet are hot normally.

smartwool merino wool socks from 35-45 degrees.
above, plus neoprene over booties from 25-35 degrees.

If below 25, I'll wear Lake mxz 303 fat biking boots and spd pedals. I wear thicker socks with them at around five degrees, and two pairs of thin smartwool socks for around negative 15-25. Yep, it gets cold here.

The plastic bag is very effective for warmth, but also traps moisture. My feet sweat a lot so as I got more equipment I moved away from plastic on my person, which doesn't breathe. But, you can't beat free.

Live in Minnesota here:

Boots, shoe covers are not enough. Make sure you size up, you want a small pocket by your toes to create a warm breathable environment for them. If they are snug and tight they won't be as warm.

I ride in OMW Bontrager boots, I have multiple friends who swear by lake boots or if you want the overpriced name brand boots go with 45Nrth.