Gail the Goldfish (my favorite goldfish) gurgles: I'm going to a wedding in Chicago in early November and realized since I've been wearing the same dress to every wedding I've been to for the past 3 years, it might be time for something new. The ceremony is mid-afternoon, reception starts early evening at a pretty fancy venue. Dress isn't specified, so I'm guessing cocktail? I'm pear-shaped, about a 2 on top and 4/6 on bottom, would prefer to keep it under $150 or $200. Greens and blues are favorite colors (I'm very pale). I'm a big fan of the 1920s/art deco look, so bonus points if you can find something that looks Great Gatsby-inspired but not a costume, even if it's just an accessory.
Fall has become the new, hot wedding season (sorry June, you're out, October is IN.)  I know this because *I* got married in October, thinking naively that it would be LESS popular - ha - was I proved wrong. Of course, since fall foods, fall colors, and fall weather are all my favorites, I was still fairly pleased with my decision. That being the case, Gail - I strongly doubt you are the only reader of this fine blog going to a wedding or three in the very near future. And though I handled wedding guest dress styling recently, I haven't done a dress post yet for this fall. What an omission! So here's what we're doing in this post - some of these dresses will be specifically for your request [i.e. Gatsby inspired dresses for a fancy evening wedding in Chicago].* I also assume that, if not specified otherwise, this wedding is likely fancy cocktail attire.  And some others will be intended for more general appeal - in a range of dressiness. I will try to specify which ones are meant for you, but hopefully you will be able to figure it out. :-)

*When I say that I'm assuming the dress should be a dress for an evening wedding, I generally assume the dress you wear should jive with the time the reception starts and not the ceremony.  As a Catholic, my ceremony was several hours before my reception (which was a dinner reception) - and most Catholic ceremonies will be the same way - because there are Saturday evening masses that conflict with having an evening ceremony in a church (and all Catholics have to get married in a church.)  Hence what we fondly refer to as the "Catholic gap."  

Now moving on from my little digression and on to the dresses!
Carmen by Carmen Marc Valvo Long-Sleeve Colorblock Jaquard Dress at Neiman Marcus ($138 - I think this dress is really cool, though the color is a little unclear. It looks blue to me, but the dress is described as black and purple lily by Neiman Marcus.  So who knows.  This is also a nice option for people who like long sleeves - which is super rare in cocktail dresses.)
Yoanna Baraschi Women's Voodoo Flapper Dress at Amazon ($142.07 - I sort of love this dress - the way it mixes modern color combo with a flapper vibe. Head's up, this is a huge discount and only a 4 and an 8 are left, so you'd have to order quickly. Also read the one review - you might need a slip with it.)
Michael by Michael Kors One Shoulder Jersey Dress at Neiman Marcus ($78 - GtG, I like this dress for you because its green but still quite simple so you could wear it for years to come. Plus its a pretty great price. The smallest size available right now is a medium so the only hitch would be if it ran large.)
Eliza J Beaded Satin One Shoulder at Nordstroms ($148 - I usually do not like satin at all, but something about this red satin number really does it for me, I think its the ruching [which seems insanely flattering] combined with the beading and the interesting back makes this dress very appealing.  Plus the color is beautiful.)
T by Tadashi Off the Shoulder Bandage Dress at Nordstroms ($138 - I've recommended this here before, but I think this simple, off the shoulder bandage dress would make a great wedding guest dress.  Probably its biggest drawback would be that it would make many traditional bras difficult, but a strapless bra really isn't that hard to come by, now is it? It comes in several great colors, including this royal blue.)
David Meister Ruched-Front Cocktail Dress from Neiman Marcus ($142 - This green dress would likely be really flattering on a pear shape. It might be a wee bit casual for your wedding Gail, but with the appropriate shoes and blinged out jewelry (I'm thinking gold gold gold) I think it would work - the lace on the back is a nice touch. Plus the green is lovely and its a killer deal.)
Lauren by Ralph Lauren One Shoulder Gown in Cottage Plum at Bloomingdales ($180 - This is got really for you GtG, but for my readers who have formal weddings to attend, but don't want to break the bank to do so, I love this Ralph Lauren gown. It's simple and sleek, but still special enough to work for a black tie event. And the purple will make it stand out from the sea of black. Add a belt and you really have something interesting.)
Vince Camuto Faux Leather Detail Sheath Dress at Nordstroms ($178 - this dress may be veering a bit towards work for a wedding, but with appropriate accessories I think it can be directed back towards wedding. I also think its a truly spectacular fall color and [as on the model] would look great on a very pale person. Paired with other jewel tones and gold jewelry it would look really beautiful.)
Aqua Dress - Angelina Beaded Tank in black and silver at Bloomindales ($158 - I like this tank dress with the shiny teardrop design for the Gatsby type theme you wanted [though I haven't seen the actual movie.] There are a couple of concerns; it may be a bit short depending on your preference and you might get cold, but a wrap should help with that. There is also a grey and gunmetal version, but I worry that it is too close to white for a wedding.  I would pair this with some colored accessories, maybe, to bring some interest to the dress - but I'm not sure what colors quite yet. I've seen some other version of this same dress, like this one for instance, that are much cheaper - but they also tend to LOOK much cheaper. I like that this one looks to be high quality and classy.)
French Connection Dress, Lily Jaquard at Bloomingdales ($228 - though with the sales at Bloomies right now, you should be able to get it for under $200.  I think this dress, which is in many ways utterly modern, also flirts with the shape and attitude of the 20s-era Gatsby dresses with the lower neckline and the feeling of a slightly slinkier tank dress. I might just be imagining that, but I also just think its very pretty and would be a great go-to dress for many types of events. It would also go great with tons of accessories. There are lots of similar dresses out there, but this is my favorite I think. If you would like to see some of the similar dresses, follow this link to the "google shopping" search for this dress - which shows similar dresses at other retailers.)
Tadashi Shoji V-Neck Trim Fit and Flare Dress at Nordstroms ($198 - this dress, or ones very much like it all have great reviews at Nordies and strike me as a great dress to wear to lots of weddings and events for years to come [a little special and interesting but unlikely to become dated.] This is one of my favorites though because of the v-neck line instead of the boat neckline that many of them have.  I also LOVE this one - but it is tragically well out of the budget.
Ivy & Blu for Maggy Boutique Pleated Jersey Fit and Flare Dress at Nordstroms ($148 - for those of my readers looking for a simple, go to cocktail dress for networking events or weddings that hits the middle on the dressiness level, this dress might be perfect. It comes in the three hottest colors this season (and three of my favorite colors for that matter): fuchsia ("acai"), "bright purple", and turquoise. I bet it will also go on sale though - if you wait long enough (though popular sizes may go quick.))
Pim + Larkin Embroidered Shift Dress on Piperlime ($69 - I like this shift dress and I think it could be dressed up enough with blingy jewelry, either in silver or gold [or better yet - copper or bronze] to work for any cocktail-type wedding. My only hesitation for you GtG is that I'm not sure how shift dresses work for pear shaped women? But it is very pretty.)
Diane von Furstenburg Raquel Knit Sheath Dress at Nordstroms ($175 - I sort of love that this dress [also available in navy blue and black] is like the ultimate blank slate.  You could add basically any accessories to this dress (belt, long necklace, short necklace, layered necklaces, crazy shoes, bracelets, literally anything) and it would work. Or you could add minimal accessories and it would be clean lines for a low-key cocktail affair. Throw a leather jacket and moto-boots over it and your ready for a night on the town with the girls.)
Tadashi Shoji Mixed Media Fit & Flare Dress at Nordstroms ($348 - this dress is tragically well out of your budget GtG, but I am putting it up here for any of my other readers who might be looking for a little black dress with a different take [whose budget can handle this.]  I actually love the cap shoulder and back detailing of this dress and, while I usually don't love lace, I think its very well done here.  If I had the budget, I'd definitely want to check it out.)
Calvin Klein Pleated Dress at Piperlime ($128 - I like this vertical black and white striped dress (it looks a little blurry when small, but when you make it bigger, it looks less headache inducing.) You very rarely see vertical lines so this is unique and fun. Probably flattering as well!)
Eliza J Tulip Sheath Dress in polka dot at Nordstroms ($148 - sorry, I am required by law to post at least one adorable polka dot dress per blog post about wedding guest dresses.  Ask my friend Katie who lives in the Midwest, she'll tell you. And while we're on the topic of cute black and white dresses, this Jessica Simpson houndstooth dress is pretty great too.)
Ark & Co. Paisley Dress at Piperlime ($79 - this has turned into the black and white print row - but I regret nothing. I think a pretty black and white print dress is a great alternative to the little black dress we all have in our closets. This paisley dress is lovely and I don't know why but I just LOVE a good paisley. Is this something that is passed in utero from our mothers? I don't know - because I'm not even sure my mother LIKES paisley...)
So Gail, and everyone else, I hope those ideas appeal to you! Do you have a "wedding uniform" you wear to every wedding?  How often do you update it? Have you bought any dresses this fall for weddings? If so which ones? Leave a comment in the comments below!
 
Frequent reader and all around awesome human CBackson submitted this request:

So I'm heading to a gala in NYC in early fall. It's black tie, and although I know that frequently means cocktail (and I'm willing to think about cocktail), I'd love to wear a long dress. The problem? Everything I see looks too bridesmaid-y, too prom-y, or too old (like, beads everywhere). I'm 32, and although I dress in a fairly classic style, I'm thinking something modern would be a fun change for me. I'm a fair-skinned blonde, on the short side, and slim-bordering-on-skinny (I'm a size 2/4, with a fairly boyish figure). I would LOVE to get something that wasn't black. Other than that, I'm open to all kinds of craziness (except maybe animal prints; girl's gotta draw a line). I was thinking $400 max, but would go higher for something timeless.

So, there's something I have to confess to you - my dear readers - there is almost nothing I like more than shopping for gowns, especially for other people (so I don't have to pay for them.)  So of course this request from my beloved C. Backson is right up my alley. I'll try to give you a variety of different looks from different designers and in different price points but, for the interested, I've become more and more drawn to the Tadashi Shoji dresses I've seen at Nordstroms and other stores on-line lately. T.S. seems to design dresses that are classic while still having a little modern edge or something that makes it just a bit different.  So there's a better than average chance that a couple of those will sneak there way in here. But I'll make sure to mix it up. :-) 

As for the dresses themselves, I think generally something with a fairly slim fit will look great on you.  First of all, you should take advantage of what sounds like a lovely, slim figure.  But in addition, since generally there's a mix of cocktail length and full-length dresses at these sorts of events, you may be more comfortable in a dress without too much poof.  But that certainly doesn't mean your dress can't have some pizazz.  Okay!  Now on to the recommendations!
Alice + Olivia Open Back Embroidered Maxi Dress at Net a Porter ($395 - from the front this dress looks like a pretty simple lace/embroidered gown, but turn it around and its DAMN sexy.  And honestly, even the lace has a little something sexy about it.  Plus, I actually like high necklines like this on dresses because it creates a wonderful base for jewelry.  This red would be a lovely color for fall.)ML by Monique Lhullier Crisscross Chiffon Gown in emerald at Nordstroms ($298 - what drew me to this dress, first and foremost, is the color.  I think if you want to stand out that a kelly green gown is really the way to go.  Plus, the cut would be flattering on almost anybody and since you're relatively flat of chest I don't think you have to worry about the crisscross neckline [which I think adds some much needed interest to the gown.]  I would consider the possibility of adding a belt at the waist, but that might drag it into the bridesmaid looks, so perhaps just gold or silver jewelry?  Or, if you can find it, navy goes wonderfully with this shade of green so navy and gold jewelry would look fabulous.)
Nicole Miller Printed Wrap Bodice Gown at Neiman Marcus ($208 - I'm not always one for prints on gowns, but I'm sort of drawn to this one for some reason, perhaps because its not *too* busy, you know?  Also, I like that the cut is relatively simple - though I would add some color in the accessories I think. Heads up though - the only size left is a 4 which I know is the upper end of your size range - but I wanted to throw it out there anyway.)

Notte by Marchesa at the Outnet ($394.50 - I think I have recommended this dress to someone before but it remains one of, if not actually, my favorite formal gowns that I've seen floating around out there [though I think when I first saw it was in navy but this lovely coral would do wonders for you.]  And sizes 2 and 4 are the only sizes left!  The gold embellishments add just enough interest to make the dress interesting but otherwise it is a very simple cut.  It is not too grand for the type of event you're going to, but you could wear it to basically anything requiring a formal gown.  Basically, I love this dress - though I realize that other opinions may vary.)
Tadashi Shoji Portrait Collar Pleated Mesh Gown at Nordstroms ($298 - so I know I have also suggested this dress on this blog before [and to you on the 'rette when you first floated this question], plus its basically black, but it is also one of my favorite formal gowns that I've seen in years so I can't help putting it out there as a serious option.  I think the elaborate collar would add a little something at the bust area and the underlay of cream keeps it from being traditional black.  Either way - this may be more my taste than yours but I wanted to include it anyway.)
Twobirds Convertible Maxi Dress in Deep Ocean at ShopBop ($310 - technically a bridesmaid dress, but its a lovely color.  I'm not sure what to do with the different ways you can wear it, but I like the one shoulder design and the color would look awesome with what I think your coloring is.  This is a simple but yet lovely dress and the pleats add a little something special.  Definitely something to consider.  I'd style it with purple and gold shoes and jewelry - perhaps go with a slight peacock look.)
Tadashi Shoji One Shoulder Illusion Gown at Nordstroms ($368 - going back to red and Tadashi, if you want something a bit more form fitting and in the almost mermaid category, I don't think you can go wrong with this dress.  It has the best elements of a bandage dress, but the illusion striping at the bottom and the neckline add interest and enough pizzazz that you'll be making a statement.  But not the sort of statement you *don't* want to make.  Actually, I really like this dress a lot, but don't think I have the figure to quite pull it off - it sounds like you might though!  There is a similar, non-one-shouldered in cobalt that is also lovely if that tickles your fancy.)
Kay Unger gold silk and metallic lace overlay party dress at Bluefly ($347 - so this last one I'm recommending in case you decide to go with a cocktail length dress because, quite frankly, it is a FABULOUS cocktail dress and when else do you have an excuse to wear a gold silk and lace cocktail dress except at a formal gala like this?  Plus, lucky you, only your size is left.  So I'm throwing it out there as an idea, as a counter-balance to what I hope you found were helpful gown ideas.)

So okay!  I hope you found these ideas helpful!!  I know it was fun finding them for you.  Write back when you pick something if you need help picking jewelry and/or shoes (because you know what a BURDEN it is for me to vicariously shop for jewelry or shoes.)  But no matter what, let me know what you go with!  I have to live through my friends and internet friends who get to go to grand galas since I spend most nights at home in pajamas.  So have fun!  Don't partake too heavily in the open bar.  And show off that dress girl, because no matter what you pick, I know you'll look fierce.  Happy Shopping and may the Odds be Ever in Your Favor.