Love, Loss & What We Wore

Some of us have had a romance we’ll remember until the day we die. Most of us have had a life-changing family or career moment, or a poignant life experience we’ll never forget. Ask a guy what he was wearing when that moment transpired, he’ll likely come up short. Ask a woman, well, that’s often a different story.

Writer Ilene Beckerman was onto something when she wrote her now-classic book Love, Loss & What I Wore. She understood that many females are detail oriented when it comes to remembering important events, especially those concerning matters of the heart. The fashion obsessed among us can even recall, down to the last button or bit of lace trim, what we were wearing when these moments transpired. Combining whimsical illustrations with a lifetime of memories both good and bad, Beckerman recalled the outfits she was wearing when these pivotal events took place. Of course, the clothes do not make the woman—or the moment. However, the image of outfit we wore during a particularly emotional time may very well be etched on our brain forever.

What was your most memorable outfit? Enter Red Typewriter’s first contest, “An Outfit to Remember,” for a chance to win a copy of Love, Loss and What I Wore, as well as a chic Red Typewriter tote bag. It will only take a minute, so enter now!

Beckerman’s colorful and heartfelt book was eventually turned into a hit Broadway play, written by the incomparable Nora Ephron and her sister, Delia. The show is still going strong, and night after night, a female-dominated audience laughs and cries together as an amazing lineup of actresses recite colorful stories about those little (and sometimes big) moments in life when fashion and passion collide.

Realizing that Red Typewriter‘s readers are both stylish and passionate, we thought it would be fun for our regular staff writers to recall some of the outfits from our past that we’ll never, ever forget, for better or worse.

Enter Red Typewriter’s “An Outfit to Remember” Contest for a chance to win a copy of Beckerman’s book and a chic typewriter tote bag!

“My mom married my stepfather when I was 8, at an outdoor ceremony in Michigan where I grew up. It was her third marriage. I was in the wedding. I guess you could call me the ring girl. My mother made my dress. It was a delicate, periwinkle cotton dress with a pattern of tiny dark-blue and white flowers. The sleeves were slightly puffed and the dress touched the floor. I felt beautiful and grown-up in it. I knew I was part of something important and life-changing. Divorce breaks everybody’s heart, rendering a tear right in the center of your life. But that wedding day was a fresh start. There is a picture of me from that day, handing the ring to the man who would become my stepdad. I look serious and very, very young. Now, 36 years later, they’re still married and the dress still hangs at the back of my mother’s closet. Maybe it’s waiting for some other hopeful kid to wear it, though, please God, not at my third wedding!” —Emily Koch McNally

“I went through this phase in college where everything had to match. I’m not sure why exactly, but I thought it was cool. On this particular day I had on a geometric-print tank top with very bright colors, including pink. My pants were also pink. I probably had some of those pink jelly shoes too. And I think there was a pink purse somewhere in the outfit. At one time I even owned a fluffy, fake rabbit-fur pink coat (but that was in middle school). Luckily I didn’t dye my hair pink, just a nice coppery-yellow, mushroom-top, layered cut. Anyway, this outfit sticks in my head, because I was wearing it while drinking from a water fountain in a dorm in Cincinnati and I was hard to miss. Apparently, I caught the eye (hard not to in that getup) of a long-haired blonde boy from California who would turn out to be…my husband! I don’t think he’d ever seen anyone dress like that before. Ironically, I don’t have a single pink thing in my closet today. Go figure!?” —Courtney Schrieve

“I went to my first costume party only three years back. I had been invited to a few over the years, but somehow I never actually could do the costume bit. This, however, was a really good friend’s birthday and I had been threatened on pain of death to come to the party in a retro costume. I had no idea what to wear until I decided to go as a ’60s Bollywood star. I had a shift dress in a lime-green brocade fabric that I had bought in China many moons back and had never worn. For years it had been glaring at me from the back of the closet. I put on the dress, got a ’60s hairdo and cat eyes to match. I added big hoop earrings and dozens of jangling bracelets, and a friend let me borrow a pair of go-go boots. I was transformed! I was the belle of the ball that night. I can’t remember a more fun night and it has become one of my fondest memories of Jakarta. Many pictures were taken, but all that survived is a picture of my eyes with the ’60s makeup.” —Renuka Hariharan

“I will never forget when I was in sixth grade and my family moved to the other side of town. It was my first day at my new school, and even though it was a chilly day in February, I decided to wear my favorite raincoat. I loved the bright colors and cropped style. The zipper zigged a bit off to the side, so when it wasn’t zipped all the way, the top flopped down casually and gave the jacket a cool moto look. The material was slick and shiny and patched in neon green, yellow and fuchsia, and the zipper was black and chunky. Wearing that jacket gave me the confidence I needed as I walked over to my locker and felt everyone’s eyes on me. It must have worked, because rumors surfaced later that day that a ‘new hot girl’ had moved to the school.” —Lisa M. Cavallari

“I raced to the starting line. The 200-meter dash at the Chicago regional meet was about to go off and I was not where I was supposed to be. I scrambled out of my scratchy track hoodie in a panic to expose my sleek track singlet. Just wearing it made me feel faster. I looked down to find I was wearing it inside out and backwards! Red-faced, I quickly switched the tank to the right direction just before the gun went off, praying that the opposing male track team didn’t see anything and thankful for the ease with which the soft fabric slipped on and off. The outfit felt like light silk happiness and as my spikes hit the track, my aerodynamic outfit easily followed. I ran with joy and the awkwardness of a freshman in high school.” —Katherine Timlin

“A few years ago, I finally scored a job interview with a company I had been trying to get into for years. It was truly the first job I had really wanted in a very long time (for more than just the steady paycheck). I knew I had to kill it in the wardrobe department since the company was in the business of fashion. After ditching my usual denim and blazer uniform, I went for the dress, the one that had been sitting—tags still on—in my closet forever. It was a beautiful blue print number from Barney’s private label: form-fitting and chic, but not too revealing. My favorite shrunken black Theory blazer was the perfect cover. But the real show-stoppers were the accessories: killer heels (peep-toe pumps in a buttery blackish/plum leather by SF brand Twenty-Two Shoes) statement earrings, my lucky watch courtesy of Dad, and a luxe, black Furla satchel that rarely saw life outside its dust-bag home. P.S. Didn’t get the job but who cares? I definitely looked fabulous.” —Gail Goldberg

“I remember going to my best friend’s birthday party in the late ’80s and wanting to wear something really fun and memorable. I was still in love with the white tube skirt Madonna had worn a few years earlier in the Material Girl video, and I happened to find a similar skirt in a local store that I loved. I paired that with a white-ribbed cotton tank top, a long yellow jacket (with shoulder pads, unfortunately) and a pair of black-leather ankle boots, a la Joan Jett. Of course, I had the ubiquitous chain belt dangling from my hips and a bunch of rhinestone bracelets decorating my wrists, but the resulting outfit looked completely original and made me feel grown-up and ready to tackle the world. I had a great time “coming out” as a fashionista that night, and so began my lifelong love affair with clothes. It’s about the only outfit I miss from that decade, aside from my black-leather bomber jacket, which I may still have somewhere.” —Maryann LoRusso

What was your most memorable outfit? Enter Red Typewriter’s first contest, “An Outfit to Remember,” for a chance to win a copy of Love, Loss and What I Wore, as well as a chic Red Typewriter tote bag. It will only take a minute, so enter now!