Say "Yes" to the Dress

Yesterday, we took good friends of ours out for a fancy schmancy brunch at one of our seaside town's yacht clubs. My daughter wore a dress.

This is the part of my story when the heavens separate and little animated angels and cupids flit about, joyously playing horns and harps. (Think Monty Python and the Holy Grail.)

My daughter wore a dress. "Hallelujah!"

If I had the time or inclination to write a parenting blog ten years ago, my daughter's choice of brunchwear would not have been the least bit newsworthy. Back then, she only wore dresses. In fact, she only wore pink dresses. I basically scoured sale racks and the children's department at Marshalls for any and all things pink so she'd have enough dresses to get her through preschool and playdates without my living in the laundry room. She had lacy ones and sporty ones, long ones and short ones, preppy little Ralph Lauren jumpers and over-the-top dressy numbers with Disney princesses.

All dresses, all the time. And, all — did I mention? — pink.

Just before her sixth birthday, my daughter started riding lessons. Suddenly, we were buying breeches and boots. She expanded her school wardrobe to include sweaters and pants embroidered with ponies. She wore blue jeans. As the first graders started categorizing their peers, "So-and-so's a tomboy," "Whats-her-name's a girly-girl," she became more and more sporty.

Good-bye pink; good-bye dresses.

Oh, I could still get her into an appropriately frilly Christmas outfit for annual pictures or a trip into Boston to see the Nutcracker with her grandmother. But, that was about it. The rest of the year, no way, José. The more she could look like she was going to a stable, or coming home from a stable, or actually at a stable ... the happier she was.

Then, one day a few years ago, she announced that she wasn't going to wear dresses. Anymore. At all. Ever.

In fairness, my daughter's mother (uh, yes, that would be me) practically never wears dresses or skirts either. My idea of getting dolled up is a pair of flowing black silk pants with an embroidered Asian jacket. So, I didn't really feel I could insist that she say "yes" to a dress. But, my willingness to respect her style didn't make life any easier. It's fairly simple to find elegant pantsuits for women my age. For tweens, not so much. I had to get creative: black satin jeans with a white silk blouse, velvet tracksuits with rhinestones. She was always presentable, and arguably more stylish than the other girls, I guess. But I have to confess, I missed my pink princess.

The road back to dresses took some time, and it was marked by a handful of specific milestones. For example, the year my daughter turned 13, so did most of her friends. That meant more than one opportunity to party with her homies at a local synagogue. Not only did all the girls wear dresses, but many also wore loads of makeup and extremely high heels. Happily, we embraced the dress idea (albeit reluctantly), but stopped short of completely tramping it up.

At about the same time, the other students in my daughter's riding class were turning sixteen. (Having ridden more than half her life, she's at a fairly advanced level for her age.) Most of the time, these older girls are in jodhpurs or jeans and caked in hay, if not horse crap. Suddenly, my daughter saw that they were willing to get a little glamorous. They still rode as fast and jumped as high; they were still serious horsewomen. But, they cleaned up real nice.

The final stop on our journey, was our cruise earlier in the summer with my best friend and her college-bound daughter. Under this older girl's approving eye, my daughter not only wore the dresses I'd forced her to pack, but she bought two more while we were on the trip!

So, back to our brunch. Our friends had brought their nine-year old daughter who was wearing a frilly tiered dress over a pair of leggings. She looked adorable. My daughter was in a short, flirty dress, snakeskin patterned with a ruffled skirt. It was a gift from my mother who has never accepted the "no dresses, no way, no how" edict. I had to lend her a pair of my shoes (the years-old aversion has led to a severe lack of appropriate footwear), and she also looked adorable.

So now that we have finally broken the dresscode stalemate, I'm thinking ahead to the holidays. After being denied for so long, I am eager to hit Saks or Nieman Marcus and buy the most classic party dress I can find. However, I know better. At this stage, I'm not dressing my daughter; she is quite definitely dressing herself. I can maybe, kinda, sorta point her in the right direction.

But the decision — and the dress — will be hers.