Upgrade Skyrim to Legendary Edition

No, it would be cheaper to get all of the DLC on sale, maybe during the winter sale, Skyrim is always on sale then. LE is cheaper to get everything if you don't own Skyrim, but otherwise just getting the DLC is cheaper.

EDIT:Just looked at the prices, it would actually be cheaper to get the LE. I don't own Skyrim, and haven't looked into it, so I assumed that the DLC would be 75% off like the base game, while it is only 50% off. Once you have Skyrim & one major DLC, it is cheaper to get the DLC during a sale.

Always check the LE's and the separate DLC's price at sales. It's a little strange, but usually LE is cheaper, because it has all the DLCs, the base game, but if you check it anytime on steam, there is a 'bundle' price: it costs less than the actual content would. If you add up with little madness-thingy, like legendary aditions is -66% or -75% at sales, while DLCs usually getting only -50% off, sometimes it's cheaper to get the full one. Just be careful, not impulse-buy: compare the separate prices and the full package's price at sales :)

Thanks for the info guys

It's the same with other Bethesda titles, like for instance Fallout 3 and New Vegas. Buying all DLC's a rip-off... It twice the price of GOTY/Ultimate Edition. Someone got irradiated...