Might have helped the sky a little, but...
Like I said, it would be just a starting point. Under these circumstances pushing the subject would have likely been too extreme by itself. You'd likely need to place the shirt in like Zone VII-VII 1/2, pushing up to three(!) stops and pulling the highlights some.
Madison - to do this you'd find the brightest portion of the subject and spot meter that area, increase exposure by 1.5-2ish stops and apply an inverse "S- Curve" to the image, making the darker regions brighter and the brighter regions darker. Be sure that this is done in raw mode.
Likewise try metering the sky and placing it in Zone VIII-VIII 1/2 by increasing exposure by 3 to 3.5 stops and again adjusting in post. That would ensure that there is plenty of data being recorded in the sky but providing some headroom for the subject.
You can check other regions. Ensure your brightest area does not exceed four and one half stops less or greater exposure from null (the zero on your meter when AE bias is zero), and anywhere there is useful detail no less than or greater than 3 stops.
You can do this all with AE, but manual exposure helps a little since you don't normally bias the meter.
One thing to keep in mind is that 90° from the position of the sun the sky is typically at Zone V, or ±0 on your meter reading. So under ideal conditions, regions that are fully illuminated by the sun will be "properly" exposed by metering this part of the sky. You can find 90° zenith by pointing your finger toward the sun, forming a "gun" with your thumb. Where the thumb points is where you can meter from. So you can increase exposure some from this point to compensate for indirectly illuminated subjects, but I wouldn't go beyond three, at most three and a half stops. So if your indirectly illuminated subject is within three and a half stops from the region of sky at 90° zenith, you should have sufficuent latitude to get everything.
The sky will appear washed out, so you'll need to compensate that when processing the files.