1. Dresses make me feel sexy. When I wore jeans, I had OMG I AM SO FAT! moments all. The. Damn. Time. It seemed like I could never get a pair that fit right- if they fit in the waist, they strained over my thighs, if they fit my thighs they bagged in the waist, they rubbed all over the place...it wasn't pretty. I would look down and notice something squishing out or pushed in and spend the rest of the day wangsting about how "fat" I was. (I'm 5'5" and between 135 and 140 pounds. Not a supermodel, but I don't think I'm fat by any stretch of the imagination.) It's different when I wear dresses. I look down and see the skirt gracefully cascading over my legs, the dress emphasizing the parts I like, like my stomach and calves, and camouflaging those I don't, like my thighs, and I think "Damn, I look good!" I feel a lot more self-confident, and the better I feel about how I look, the better I look.
2. Dresses make ordinary activities feel like adventures. When I'm wearing jeans and a t-shirt, I'm an ordinary person doing boring things. When I'm wearing a bat-print dress and striped tights, I'm the heroine of a Tim Burton film, finding the light side of dark things (or is it the dark side of light things?) in a twisted fairy-land. When I'm wearing a fifties vamp dress, I'm the femme fatale in a film noir, waiting for Phillip Marlowe to sweep me off my feet even as he discreetly checks my bag for my Lady Derringer. Maybe this only works if you have an overactive imagination and a penchant for making up a story to go with everything as I do, but it's another good reason to try wearing a dress; who knows what imaginative brain cells have been pushed into a stupor because jeans don't tell a story, and a dress does?
3. Dresses hold memories in a way that other clothes can't. I took a bunch of jeans on my England trip the summer after 9th grade, and I don't think I ever thought "Oh, this is the pair of jeans I wore in Glastonbury!" when I wore them again after that. I did take dresses to New York the summer after my sophomore year, and to Washington D.C. last year- and every time I pull on one of those dresses, I remember "This is what I saw The Lion King in" and "This is what I was wearing when I got to see the Capitol building in person." On my hoped-for backpacking trip around the British isles after I graduate from college, I am going to take nothing but dresses. When I'm a movie director, I plan to wear dresses all the time. I want to be 90 years old and telling my granddaughter "You take care of that alphabet-block print dress now, missy; I wore it when I was shooting my first picture!" The Sisterhood of The Traveling Pants aside, you never hear about someone handing down a beloved pair of khakis. But you do have heirloom dresses, and heirloom dress memories. My eighteenth birthday is in a few days, and my mom was just telling me today about the three dresses she got for her eighteenth birthday. She still remembered the cut, pattern, color, and detail of every one. She's forty-nine. My great-aunt has often reminisced fondly over a skating dress she had when she was thirteen; she's 88, and still remembers every detail of that dress. You just don't get those kind of memories out of a pair of Levi's or a button-down shirt.
4. Dresses make me happy. When I'm wearing a dress, I feel like myself. I really don't think I need any other reason to wear them, actually.