No, it does not need to match. In fact, it often looks better if it doesn't.

It doesn't need to match, but I like it when pieces in a room at least "relate" to each other.

You know, the three and four dresser drawer aren't so full of squares that it is an obvious match . . . and you can disguise matchiness with accessories, such as lamps and art on the walls and so forth . . .

When you read design magazines is the furniture in any room ever a set? Never! It should look good together but I don't think it should all match.

Absolutely not! You have clean lines going on, so i'd incorporate that into whatever piece you're thinking. But, it doesn't necessarily have to be squares. You might even consider bringing in an additional style - damask patterns somewhere would go really well in this space. That would hide anything from being too 'matchy'

It doesn't all have to match, and the results can be boring, generic and predictable if everything's matchy-matchy. I think it's more important to pick pieces you like while keeping relationships and contrasts in mind. If you go with the dresser you suggested, break the squares with rounded accessories. If you choose a contrasting dresser, bring in a square echo.

It doesn't need to match, but the real question is what do you like? If you like the look of the West Elm dresser then by all means get it. lucidez777 had the right idea to then play with your accessories.

It won't look bad - I mean, it matches! But it won't look so good, and it's a missed opportunity to add a bit of life and interest to the room.

Think too about how you'll feel if you don't like it so much in a few years; you'll have a whole set you don't want rather than just a couple of pieces to swap out.

I say don't do it!

I think that the cube cutout is subtle enough that it's not overwhelmingly matchy-matchy with the headboard. However, your complete bedroom set will look like exactly that: a complete bedroom set.

I personally prefer a common/complimenting color scheme with a (mild) style theme between the pieces. For example, all of our bedroom furniture is cherry, but everything is a slightly different stain since the pieces were bought/created piecemeal from different sources. The common style is "modern, leaning towards midcentury clean lines"; the common elements between pieces are cherry wood/white metal/glass.

your answer is in the question. If you do not feel confident enough to pull you own eclectic look, if you did not determine or simply have a feel of how you want your bedroom look and function, do not rush into it. any room has a story to tell. the story of you, your likings, your travels, your comfort level, your personality. Miss-match look is alluring and intriguing...but not as easy to achieve as it might seem. There is nothing wrong with having two pieces from the same line. You can dress your bedroom in so many different styles. But i would not recommend spending any substantial amount of money on any furniture piece if you are not sure.

I think it's easier to make something look nice when it matches...though I agree that a well-executed design based on non-matching pieces looks much more sophisticated. I can tell you what NOT to do: don't buy multiple dressers from Ikea in beech in different styles (voice of experience--currently trying to correct that mistake).

Oh man... the matching end tables is always the death of me.
(getting two different end tables is KEY to breaking up the monotony).

Instead of getting that matching dresser, in that dark wood, why don't you go with something really divergent: A mirrored dresser? Don't want to drop the cash, why not something like an antique Chinese or Tibetan dresser. Something ethnic always softens the way your room may begin to feel too monochromatic. Get something antique. In any type of wood grain, or painted. It would really add interest to the room.

please do not subject your children to matching furniture... i grew up sharing a small bedroom filled with two identical wood beds, dressers, night stands, and head boards. It felt like a lumber yard

On the contrary, matching furniture looks... well, boring and soulless. Let yourself feel confident, especially in your bedroom, and go with some interesting pieces that engage and challenge one another, pieces that have an exchange.

For inspiration on how to pull it off, check out Domino and Living Etc. -- don't be intimidated, it is not that hard.

I subscribe to the school of thought where if you buy things you love, that's all that matters. You will be surrounded by lovely things that don't necessarily match but who cares!

Some suggestions for your room:

First choice:
Drawers:
http://www.grahamandgreen.co.uk/product.aspx/bone inlay furniture/pink mother of pearl inlay chest of drawers/furniture/furniture_boneinlayfurniture/-/jcb8364.htm

Miss-matched bedside "tables"

On one side, Ligne Roset's Marguerite cowhide upholstered footstool (put a tray on top to hold clock, etc.)
http://www.ligne-roset.co.uk/?sec=products&pid=1&cid=9&rid=369&page=0

On the other, this white table -- I forget who makes it, but here is a coffee-table sized version -- look at the very last picture -- Francesca's house -- the white table on the round green rug (if you have anything to keep hidden, keep it in a handsome handmade walnut box) -- http://www.remodelista.com/our-houses/

Matching Furniture = Yawn...

(unless you really like the idea of living in a motel room or department store furniture display)

How about getting other West Elm dressers but still in the chocolate color? Then you know the color will match, but it won't be perfectly matchy. It is a great first step in to unmatched land.

Here's the table -- it is by B & B Italia. A small version in white would be lovely (although orange would provide a great pop of colour, which you may need with such dark wood):

http://www.bebitalia.it/collezioni/scheda_prodotto.asp?ID_Prodotto=95&lingua=en

I agree with most of these comments, when bedroom furniture look like it comes in "sets," it often doesn't look as good as picking out original pieces. In keeping with the contemporary bedroom furniture you do already have, I would suggest this dresser in white: http://www.boconcept.us/Default.aspx?ID=84533&ImageID=3470&flashimageid=0

to offset all the chocolate in the room. Plus, this dresser presents a more rectangular feel than square, and the feet that stand the dresser up on the bottom are nice and curved, breaking up all the straight lines you have.

After a long tiring day at work, all of us want to unwind in our own personal space. It is, therefore, not surprising that most people find their bedroom as the only place where they can relax and rejuvenate themselves. So, getting the right bedroom furniture is very important for providing the right look and feel to your bedroom. Selecting furniture for the bedroom requires much thinking, but it is not impossible to achieve the right look. Planning for your bedroom furniture would mean considering a number of factors. One of the major factors worth considering would be your taste and sense of styling.