2ndGen

In your opinion, what would you consider the "best" gear to ride in?

• Cap
• Socks
• Boots
• Tights
• Gloves
• Balaclava
• 2nd Layer
• Shell/Jacket
• Base layer(s)

I'm leaning towards the following brands:
-Sidi for Boots
-Gore for Jacket, Tights, Gloves, Balaclava
-Under Armor for Baselayers
-Smartwool for Socks

Already have Louis Garneau Perfecto L/S Jersey for 2nd Layer along
with Louis Garneau Race Gripper Gloves and a Pearl Izumi P.R.O. Cap.

Thanks for any suggestions.

AEO

base layer: the stuff from PBK
2nd layer: the winter sports under layer from costco, both top and bottom.

cap and balaclava, you don't want.
head band with ear flaps and face mask will work better.

scoatw

IMO, Cross Country ski gear is best for winter cycling. Check out Sporthill. Their XC pants are the best. They have a wide temp range. Showers Pass for an outer layer. Windproof and coldproof. Sporthill jacket under that. I use a Wickers balaclava. They're thin and cheap. They work well in below freezing weather. I go cheap on gloves. Cotton work gloves ($1) above 32f, mittens below that. Bass Pro Shops and LL Bean have excellent hunting socks that are made for cold weather, comfortable too. I pair those with LL Bean Snowsneakers for a warm combo. In my experience I find that bike specific clothing doesn't work as well in cold weather as much as ski gear does.

cyccommute 

Bib tights are better for cold. They trap more heat. For below about 20F, Pearl Izumi Amfibs are great. Above that and you might as well wrap yourself in plastic.

pyze-guy

I like wool, windproof and waterproof. I wear wool basspro socks, nothing better IMO. Flannel running tights, 3/4 legth climbing pants, winter cycling boots, shoe covers, dryfit tshirt, baselayer shirt, wool sweater and windproof jacket. Wool mittens under waterproof/windproof gauntlet mitts, and a thin fleece hat, snowboard helmet and googles. This is for about -10C and below.

Hezz

Sidi boots are designed for Italian winters. If your winters are very mild OK. If not go elsewhere.

Gore products are good for the money. Though I have never used the tights.

I find Under Armour over priced and under performing for a base layer. In some situations they work fine and for some people. If you ride hard and sweat a lot they do not wick or breath or insulate enough. Try cheap wicking XC or downhill ski long underwear on top for base layer. Cheaper and works better.

Several brands of tights are good. I like Pearl and Specialized. But several brands are good here.

Bike specific gear works OK but not the best for the second layer when it gets below 35 F or so. Cheap breathable polar fleece or long sleeve wool sweaters work best here. Cycling jerseys used as second layer are bulky as pockets add unnecessary bulk and insulation value is poor. Though breathability is good. Wicking is average. Cycling gear wicks well when next to skin and exposed to air stream but as a second layer it only performs OK. If only using two layers in mild conditions ( above around 40 F) cycling jersey as first layer works well (no dedicated base layer). This is only guide line. Lots of variation in insulation needs when on bike.

cyccommute 

Gotta disagree with you. I use bike specific gear exclusively. The fabrics and clothing work very well below 35F. No second layer is going to wick moisture as well as the first layer because the driving force...your body heat...is less effect at moving the moisture as you get further away from the heat source. Additionally, at temperature below 35F you aren't worried about air flow. If anything you are trying to mitigate the air flow to preserve your body heat. A jacket that blocks the wind will interfere with the wicking abilities of any fabric. Cycling gear has the advantage over bulkier fabrics in that they are more packable for changing conditions...even with rear pockets.

ghettocruiser

I don't see any info on the OP's hometown/climatic zone or expected temperatures.

Thus I have no clue what to recommend.

Staggerwing

Depends on how cold, and how far.

I like to mix bike specific with snow ski gear, as required.

For example, merino ski socks, Under Armour type stretchy base-layer top, full length, insulated cycling bibs, an icebreaker merino sweater, thin softshell top with pit zips, Hestra ski gloves, 180s type ear warmers, and clear lensed ski goggles. For me, this getup is fine for 0deg F mornings. I also have a interesting balaclava for really cold days; basically a heavy synthetic fleece neck gaiter, sewn to a thin, "d0-rag" type top. Fits perfectly under my normal cycling helmet. Never seen another like it though.

With a windbreaking layer, like a softshell, I don't need much insulation. Of course, anything that fully blocks the wind is going to trap moisture too, so it better have some pit zips, and preferably, additional means of ventilation.