Have you tried moleskin pants (Orvis) or perhaps, less expensively, 
Duluth's firehose pants? Also, try long johns under your jeans or these. 
Think in layers. Base layer, insulation layer, wind and water proof layer, 
in any combination. If 40 is a cold as you're getting, you'll be fine with 
any "normal" clothing in those combinations. 40 means if it precipitates, 
things will be very wet and cold. That is a tough combination to manage, so 
unless you are interested in going ventile (Hilltrek) just find a good 
waterproof /supposedly breathable jacket and ventilate it well as needed 
when riding. 

Cold weather riding is slower, required changes to match the conditions of 
wether and the ride itself (I have to really bundle up before descending 
the pass back home.) 

You mention pants are the most important thing. My breeches are the last 
thing to get fortified with additional layers. Managing layers at my core 
and extremities is far more critical for me. But that may just be me.

Experience is an excellent teacher. Try different combinations, ask 
questions here. You may feel like you've enough stuff on a simple day ride 
for an S24O -- that's a good thing. Better to have too much and not need it 
than too little and desperately want it.

With abandon,
Patrick

On Tuesday, January 3, 2017 at 10:42:19 PM UTC-7, Ash A wrote:
>
> This's my first season riding around in winter. When it gets down to 40, I 
> feel like my jeans and shoes aren't sufficient for a comfortable ride 
> (typically an hour or so).  
>
> I do not like to wear biking cloths that I see in bike shops.  May be they 
> are ok if I'm heading straight back home after the ride.  They don't feel 
> are suitable for riding to a restaurant for dinner.  
>
> Looking for recommendations for pants (most important), shoes and 
> shirts/jackets that look like casual wear, but provide sufficient wind/cold 
> protection while riding.   Thank you!
>

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