When deciding to reupholster a piece of furniture I ask myself “Do I?!”  DIY that is…  There are some projects that I absolutely know I can handle!  A drop in seat.  It pops out, you lay your fabric, you staple under the seat.  Voila!  But when it comes to any project (and I mean any!!) that comes to sewing, I know better than to even attempt!  I have been blessed with a few creative talents, sewing is not anywhere on that list.  So when I decided it was time to transfer my desk chair from a basic linen chair to something with a little more punch, like this gorgeous Caitlin Wilson Buffalo Check, I decided to do both.  
Both?!  I knew that I have had success in the past with upholstering the inserts of exposed wood frame chairs.  I removed the existing cording & fabric, used the removed fabric as a loose pattern, cut my new fabric & stapled it on ensuring that I was pulling tightly & keeping the pattern in line.
I repeated this for the entire outside & inside of the chair.  And the arm pads.  Now comes my trip to the upholsterer.  I informed him where my pattern needed to lie in order to match up with the chair, handed him my seat cushion & remaining fabric & let him get to work.
I also had him fabricate about 12 yards of double welt cording to cover up all of those staples.  I followed the outline & adhered it in place using hot glue.  
And after a little collaboration between the upholsterer & myself we have a completed chair.  I choose to do DIY the portion I felt comfortable with because I enjoy projects such as this & I know that I can accomplish it.  
If you are questioning your ability, but still want to learn I suggest going to the thrift store picking up an inexpensive chair & use a muslin to practice upholstering with.  As with anything else, practice really does make perfect.  Unless it is sewing in my case! LOL  (I really have tried!!) 
Otherwise, do your research & befriend your new upholsterer!!  It is always so gratifying to pick up a project that I have dropped off to be transformed.  
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xo – Kristin