You would have to check and enable your server to boot from USB, you can get in touch wtih your server vendor or go through the BIOS options (What server do you have ) ?
You can create a bootable usb flash disk (minimum 4GB recommended) for Server 2008
"""""Copy your windows 2008 DVD onto a folder in your hard disk""""""
Insert your USB Flash on a windows vista, 7, 2008 or 2008 R2 system :
Open up a Administrator Command Prompt (Right Click > Run As")
on your admin command prompt : type "Diskpart" without quotes
Do a list disk to identify your USB Disk number and then follow the sequence (replace the disk number accordingly)
select disk 1
clean
create partition primary
select partition 1
active
format fs=NTFS
assign
exit
Step 2: Make the Drive Bootable
Now you can either use magicdisc to mount the windows 7/ 2008 iso or insert the disc in the dvd drive
Insert your Windows Vista / 7 / 2008 DVD into your drive.
on a command prompt
d:
cd d:\boot
Use bootsect to set the USB as a bootable NTFS drive prepared for a 2008 / 7 image. Now check the drive letter assigned to your USB Flash drive and then type the following on your command prompt :
bootsect /nt60 g: {{{{Replace G: with your USB flash drive letter}}}}}}
Copy the installation DVD to the USB drive