The Chainlink

That rides bikes or someone that has similar "symptoms"

Been riding for 7+ years recently having a tingling/numb feeling in my toes after riding. 

At first chalked it up to bad shoes but I've always worn Chuck Taylors without issues and now with insoles.

Not cold related as it started happening in August.

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not a doc, but this sounds like neuropathy.  a friend who works in retail has this and it happens to people who stand for long periods of time. 

Call Dr. Tom, he's a chiropractor and once he started working on me my arms are less numb and he cycles -  (773) 271-3900.

Not a doc but have ya changed saddles? or do ya ride in shorts that could bind at the femur artery or lower near the knee?

If you gained weight or upped your weight training in the lower body the added mass (muscle or otherwise) could bind in the blood or nerve channels.

Do the added insoles in yer Chuck Taylors make the fit a bit tighter around the ankle or instep?

Even if yer sitting differently in the saddle (clothes, body bulk, riding position...moved handlebars,rotation,lift,etc...moved seat up/down/tilt...you may not have moved it yerself but it might be sliding in the tube or swiveling on the clamp) could put pressure on nerves. blood vessels that could cause this and a doc wouldn't be any help...but a bike fit expert might.

Jeff

If its happen in both feet, I would suggest a shoe change...at the very least experimenting with different shoes might determine what your next step (funny pun) is to solving this problem.  Could be the inserts your using creating more arch support then your use to...

Do you check inside your shoes before you put them on for scorpions, mice or other critters?

No Scorpions. I think I ride more on feet than sitting, let me look into the Dr. in a bit.

The Chucks could be the problem. Cycling shoes have a more rigid sole to distribute the pressure from the pedals more evenly over the foot. The lack of that support over time is likely to cause problems, especially if you ride a decent amount of miles. If you do go to cycling specific shoes, I would recommend   at least getting clips and straps to help with foot placement on the pedal. Foot placement is the other  likely problem. Clip-less pedals are by far the best solution from a bio-mechanical stand point, but also the safest. Just not the cheapest.

I had the same problem awhile back.  Using shoes with stiffer soles and loosening the laces a bit made it go away almost altogether.  It still comes back a little bit when I'm on a bike that stretches me out more, so there may be some merit to what Jeff was saying above about pinching of the nerves around the upper thigh.

Clip-less pedals are by far the best solution from a bio-mechanical stand point, but also the safest.

Not necessarily the safest, depending on your riding style and type of trips.  It takes a while to get used to riding with them - getting used to clipping in/out.  Unless you practice a bit first on a trainer to get used to the mechanics of it and remembering to clip out before you've slowed down to stop, you will fall.  Happens to everyone when they're learning.  It's a good idea to practice in a low traffic area before dealing with real traffic.

If you ride a lot in stop-and-go situations or you make frequent stops, you might find them more trouble than they're worth.  It's very much a personal preference thing.  Platform pedals with strapless toe clips and mountain bike shoes (stiff soles, but reasonable to walk in) are a decent low-maintenance alternative.  That's my combo of choice for my utility bike and situations where sudden, unanticipated stops may be common (such as Loop traffic at rush hour).

Riding clipped in can be great for longer distances and faster rides where you don't have a lot of traffic conflicts.

Used to happen to me all the time but not till mile 20.  I'd wiggle my toes a bit and it would go away. Once I started doing yoga the numbness never returned... go figure. Did it have anything to do with it?

I think you'd benefit to moving to a pedal with more supportive real estate like the VO Sabot or the Thin Gripster:

These big platform pedals offer a ton of support and also allow the freedom to adjust your foot position as necessary while riding. I love em for commuting, touring and anything in between. I only wear clipless while racing or off-roading.

I use PowerGrips, because I can pull up on them, they do not crush my toes pressing forward and they are super easy to get into and out of. http://www.jensonusa.com/!tZ7vWALP4S!dxmrsNzReeA!/Power-Grip-Sport-...

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