“Why yes, dear sir, I would like another drink.” 

“Oh my hat, why thank you, yours is lovely too, darling!”

We’re going to a Steeplechase next month and I could not be more excited! (I need your help at the end of this post!!)  I’ve never been big into horse racing, not for any particular reason.  I guess I was just never really exposed to it much.  But the last couple of years I’ve heard more and more about this one in the Charlotte area. 

Sundresses and hats and tailgating and friends.  What more could you ask for?

We tried to get a group together last year, but it ended up not working out.  But this year.  This year was a different story.  I was dead set on going.  Even if it were just L and I.  But obviously, it’s way more fun with a big group.

I started floating the idea around several weeks ago and got a great reception.  I just hoped that everyone would come through. 

Then I started thinking about what I would wear, because naturally, this is something I obsess about before any sort of ‘event.’   And then it dawned on me that you can’t get much preppier than a steeplechase and maybe, just maybe, if I get down on my hands and knees and beg and plead, I could talk L into wearing a tie that matches my dress.  Oh!  A Lilly tie that matches my Lilly dress!

But because I lost so much weight for awhile and then gained it all back, none of my Lilly Pulitzer dresses fit anymore, they’re all too small. 😦  So, naturally I went to Ebay.

And I hit the jackpot.  I found a women selling a cute Lilly (in a pattern that I had previously drooled over in the store) and was also selling a matching tie.  And miraculously, the dress was in my size.  And both items were a fantastic price with extremely cheap shipping (and if you’re an avid ebayer, you know they can really get you with the shipping prices).

I asked L.  And begged and pleaded.  And he agreed that if I won the auction he would wear this lovely pink and green tie. 

So I bid. And I won.

I now had our outfits.  We started looking at the pricing info for tickets, decided on what we thought was best and sent out an email to all of our friends.  And now we’ve got a big group going.  One of my friends has gathered an additional 15 other people to come in.  I don’t know them, but I think it’s going to be a grand time!

Then I started searching for a hat.  And I kept finding all of these really cute black hats.  Which would not go with my Lilly at all, but would look fabulous with the pink sundress I bought at J.Crew when were at the beach.  And I would LOVE to wear that dress, but I was really excited about this matching tie thing (I’m a dork, I know).  Plus, I KNOW L will not wear the tie if I don’t wear the dress.

But, I thought, at least I have the J.Crew dress as a back up.  You see, the Lilly is lovely and fits nicely, except in the hips.  It is quite tight. And although I have about a month and a half till the race, and I’m doing better about my eating and exercising, I just don’t know if I’ll be able to cut it.  Although, I could always wear some spanx and that would probably help.

On my way home from work last night I quickly stopped into another Stein Mart (I had already been to one at lunch, plus 2 Marshalls) to look for a hat.  I pulled into the parking space and staring back at me from the window display was this gorgeous pink and green dress.

That’s perfect, I thought to myself.  And honestly, I probably squeeled outloud too.

But I already have two dresses I could wear.  And then I realized why I loved it so much.  It looks exactly like a Molly B. dress I had found that I wanted to wear to my college graduation.  Besides the fact that that dress was $250+, I couldn’t track it down in my size.  This was my chance to finally have it – or it’s twin, anyway.

After I searched the store for hats (and found a black one as another contender for the J.Crew dress), I found the dress on the rack.  And it’s only $40 – not bad if you ask me.  I tried it on and it fits and it’s so cute.  But I wondered if the high neckline makes me look too old (I’m still having issues with this whole being 26 thing).

I used my better judgement and put it back, left the store and called my mom to tell her my dilemma.  She jokingly suggested that I just wear all three dresses and have dress changes that day since we’ll be there from about 10am – 7pm.  Ha. 

I just don’t know what to do.  I already have shoes that I could wear with any of the three dresses.  I have found hats that I like that I could wear with any of the three dresses.  I just don’t know which one to choose.  I keep leaning toward the Lilly (providing it fits better by then) because I love the idea of L’s matching tie and it’s unlikely that I would be able to get him to wear our outfit combination another time (unless maybe we go next year).

So I’m asking your advice.  Which should I choose.  Let’s just assume, for argument’s sake, that the Lilly fits fine.

Dress #1 – Lilly Pulitzer – with tie in matching pattern for L
Would wear with pearls, white or pink hat and cute pink sandals
PS – sorry it’s blurry

Dress #2 – J.Crew
Would wear with pearls, silver Tiffany beads or some sort of black beaded necklace; cute black sandals and a black hat
*it’s dark pink by the way, not red

Dress #3 – Found in Stein Mart last night – looks like the Molly B. dress I wanted for college graduation.
Would wear with pearls, cute pink sandals and a pink hat