A Marilyn Monroe-esque style could work for a star like Barrymore. She has the face and the hair to pull it off. However, this particular execution went awry in the back-combing phase. Back-combing is an art that takes practice. Unfortunately, Drew's style has taken on a life of its own. See more Drew Barrymore hairstyles.

The actress, model, singer, designer nails a modern take on retro with this easy updo. Keep the look simple and allude or hint to the vintage vibe. This turn of the century nod with a delicate accessory works great with her seventies-inspired gown. Simplicity rarely fails. See more Milla Jovovich hairstyles.

The idea with a retro style is to hint at a bygone era, not look like you were actually alive during it. This exhausted style ages the beautiful Jovovich. Danger lurks in taking retro looks too far, too fussy, too overworked. The result is an old-looking you instead of you with an old-time look. See more Milla Jovovich hairstyles.

Your mantra should be: never look like you tried too hard. Ellen Pompeo pulls off Depression-era finger waves beautifully while keeping her look tasteful and touchable. Letting the style speak for itself and downplaying accessories, makeup, etc. is a great choice. This was a great week in hair for Ellen and other celebrities.

Did we mention that you should never look like you tried too hard? Ms. Pompeo's fifties style suffers from a case of over-teasing, over-doing it and just plain going overboard. As a general rule, if you could successfully hide a hamster in your hair, you've gone too far.