It depends on your knowledge of php, html and css. If you are good on that you can do it, with codex guide from wordpress.org site. Or hire a designer, and get this done. But be careful with scammers. I suggest, you pay after the job done.
Well right said by mam......You need to hire somebody for your blog. They will convert your blog professionally and you can ask for the bonus services like wordpress training, little tweaks and seo optimization for wordpress blog too. Let me know if you need someone...
i am not sure if you have lot of static pages. Recently i switched a static site to wordpress and it had about 20 pages. i had to copy html code then copy to wordpress and it worked fine!