Heart over Heels

First there was the balding lawyer who told me on our first (and only) date that I was wearing the wrong outfit. “You should have worn a short, tight dress,” he insisted. I had not asked him for his opinion. I thought I had done a pretty good job at it, even if it had taken me twice as long to get ready. But alas, I was not flaunting enough of my goods for that to be a successful outcome. Then there was Mark. To the best of my knowledge (and this knowledge is based on one kindly edited on-line dating profile and and a disturbing exchange of text messages) Mark was not a fan of vintage, nor me, so not nearly the right material to devote an entire post to. I had never even met the man in person. Yet, it is very possible that “The Hamptons Guy” is my biggest Muse to date. Anytime anyone commends me on my Tales, whether it’s in Australia, or Belgium, or at a fashion party, my ill-fated attempt at finding love in the Hamptons is the story everyone bookmarked. Mark has no idea how famous he is! He prompted all kinds of outrage and ridicule and worry. And though both catastrophic, those men inspired the editors at British Vogue to commission me to write down my thoughts on dating as a fashion girl. My two thousand words are finally in print in the December issue, and transcribed below. Enjoy!

I met Jeff online. I had found him in my “Daily Suggestions” and made him a “Favorite”, in hopes of him liking me back. Some would call that passive-aggressive. I call it casually curious. He looked cute: dark, healthy hair, kind eyes, preppy style, divorced banker, two kids and quirky in the way he presented himself. 
A few weeks later he made me a “Favorite” back, and we got to chatting. He wanted 
to meet. Unfortunately my schedule was 
a mess and, after a few back-and-forth emails, I dropped the ball. I was too busy with the re-launch of Tales of Endearment, my blog about girls who love vintage clothing. I was shooting, styling, writing and prepping for my big story about Diane von Furstenberg; I was the first person ever to have access to her vintage archives!

I forgot about dating, and Jeff, until 
I got a new message in my inbox: “Natalie, very nice coup (DVF) for you reported in The Wall Street Journal yesterday – red lips and all. You have been busy. Hope your summer is going well, Jeff.”

Drat. My cover was blown. I had never revealed my last name, nor what I do for a living. All he knew was that I work in fashion, live in Brooklyn and am lactose intolerant. How did he recognise me? He called me later that night – after I accidently emailed him my entire signature – and told how he had simply Googled “Natalie + Fashion + Brooklyn” and a few images of me had shown up. So, whether or not he had found The Wall Street Journal article, 
he already knew my entire background, had scrutinised my blog, followed me on Instagram and had no doubt read my occasional insights on the strange new world of internet dating. Mysterious no more…

Online dating offers the advantage of anonymity. You get to make up a name and present a perfectly edited profile. I don’t want potential guys to know about my silly poses and funny outfits before our first drink. I don’t want them to know how many followers I have online, or that I get photographed outside of fashion shows. Fashion is such a fickle, frivolous industry to begin with, I don’t want men to think that’s all I am. It’s too foreign, too absurd and too intimidating. Fashion girls have this stigma of being high maintenance and prissy. I’d rather be known as a Belgian girl with a flair for vintage dresses, who hates musicals and goatees. The rest of me can be apportioned out one drop at a time, until I’ve reeled him in.

I started internet dating earlier this year. I have been divorced for almost 10. My husband was Belgian; I met him at a New Year’s Eve party when I was visiting my parents and fell head over heels in love right there on the dancefloor. He moved to New York a month later. We had a great, stormy romance. He was my rock, the love of my life. But New York wasn’t the right place for him, and we failed miserably at making our life together a success. I soon fell out of love and kicked him to the curb. This all happened before my thirtieth birthday.

Work took over where my love life stalled. I quit my job as Craig McDean’s studio manager and started my own casting agency. Over the next 10 years 
I built up a nice roster of clients, such as Hugo Boss, Phillip Lim and Helmut Lang, and became an industry staple. While most of my work was behind the scenes, I soon got noticed and eventually landed a spot in the top five best-dressed girls on Style.com. In 2010 I launched my blog, and what started as a bundle of little stories and bad photography soon had a cult following of international fans.

Since my divorce I’ve only had two significant relationships. The first one was a skateboarder. He was hot, talented and taught me a valuable lesson: never date a skater. The other guy was one of my best friends. We had an intense romance for 
a few months – we discussed baby names and where we would live – until he got “scared”. Second lesson: never date a man just out of a long relationship. Not that my single status ever bothered me especially. The past three years have been a whirlwind of travelling and late-night assignments. 
I have barely had a social life. But this year I made a change. I turned 38. If I ever wanted to get remarried and have a kid, fashion would have to take a back seat. The search for a new husband yelled shotgun but beckoned a few questions: 
1. Where to look?; and 2. What to wear?

I’m known for my idiosyncratic, eclectic style. Though “cute” and “colourful” are recurring key words, it’s all over the place. I dress in characters really. Sometimes I feel like a sexy secretary; other times I’m an English tomboy. Typically I’ll wear a dress or a skirt with a crazy print, a slouchy sweater or boxy T-
shirt and high heels. But I’m not afraid of Birkenstocks, dungarees, Nineties crop-tops and cat’s-eye sunglasses either. It’s more about how I put things together at a moment’s notice. I love the styling element of getting dressed. It’s all about balance and how it visually works in front of the mirror. The proportions have to be correct. I even go as far as matching my lipstick to my shoes! I am invited to fashion parties and client dinners on a regular basis. Contrary to what you might think is the perfect social setting to meet Husband Number Two, I’m usually part of a large group of cackling women and flanked by at least a few gay men who know more about trends than I do. The odd straight man who does loiter the corridors of fashion chases models for sport. He is irrelevant. So, for years, I have dressed to accommodate myself and other girls. It’s become somewhat of a job actually. Most of the thought goes into whether the outfit is inspiring, unique and, well, Me. So when a date comes around I am left helpless. Everything and anything 
I put on is either too sexy or too fashionable. It takes me twice as long to get ready.

Men don’t like complicated outfits. They want simple, easy-access attire: some leg, a waist, 
a skirt, bare arms, perhaps a shoulder. Nothing too fancy like gold, chunky earrings, or overbearing like fur collars; nothing restricting like corseted belts, or slouchy like oversized jeans. It’s all about mild, instant gratification and comfort, words rarely applied to a fashion situation, and words with no relation to my usual explosion of retro prints and colours. At first I found it hard to marry the fashion girl in me with the one who goes on blind dates. Early on, one guy told me I was totally off-the-mark in my cropped MIH jeans and Peter Pilotto top; I should have worn a tight, short dress. He was not happy with the minimal amount of skin on show and complained, jokingly, until we left the restaurant. I didn’t call him for a second date, but his remarks got me asking what is the appropriate attire for a 
first date?

Dressing for straight men puts me in an entirely different mindset. I’ve created a new Natalie for these occasions. One that wears flirty Cavalli dresses with skinny Casadei heels and lets her tangled hair loose. Dating Natalie doesn’t wear lipstick or heavy jewellery or platforms. She’s relaxed, loves turquoise bracelets and wears black (which I never ordinarily do). I started to fine tune my sartorial formula as soon as I got active online and I think I’ve now found the perfect package: a black, tiered silk dress by Viviana Uchitel, worn with black lace Jimmy Choo slingback heels, my gold Joosy nameplate necklace, and 18-carat hoops. The dress plunges into a deep V in the front and back, but never gets uncomfortable, and shows the skin in the subtlest way. I’ve realised that I like this Natalie, even though she doesn’t dress, look or act like my fashion persona. More importantly, men dig this Natalie, too!

Yet, after six months of boring dates and disappointing men, I have come to the conclusion that although the web is a great way to meet people, it’s the worst place to find a real connection. I get about five messages per day on average but only one per cent of them deserve my attention. Are the strong men all taken? Or do all these forced meetings and make-believe outfits defy the purpose of finding true love? Shouldn’t I just sit back and wait until one man stands up and yells at the top of his lungs: “I love this girl with her sequined shorts and Mickey Mouse headscarf!”

My ex-husband once told me he’d never met anyone who dressed like me. And if he managed to fall in love with me regardless of what I was wearing, why should I change myself? Why is Dating Natalie a necessity? Has my style evolved so much over the years that it’s become 
a romantic handicap? As far as I can remember I have always dressed differently. I got detention at school because the principal didn’t like the flared pants 
I had my mom make me. So what’s 
the difference? Or should I ask: what’s different about my ex-husband and the men I meet now? Have I pressured myself to believe that doctors, investment bankers and all those guys with regular jobs I am trying to meet are the ticket to my future as an attached person?

All I have tried to do so far is make a good impression. To get a foot in the door; to please my man. To make an effort and show him I care. But when all is said and done, and I’ve got the right dress on, it still comes down to confidence. If you truly feel beautiful and happy with what you’re wearing, it only benefits the conversation. I may feel I’m making compromises on the outside, but it’s only temporary. My personality will do the rest of the talking.

Alas, Jeff turned out to be a sweater. And I don’t mean the wool kind. No, I’m talking profuse perspiration. Our second-date make-out was the stuff of Kristen Wiig movies. His hair got soaked and swooped across my face like a mop. I had to call time out just to put a towel down. Needless to say I did not call him again. Imagine the laundry!

Black, tiered, silk dress by Viviana Uchitel at Gypsy Nation Vintage; Black lace ‘Maylen’ bootie by Jimmy Choo.

Photo by Meredith Jenks.

November 11, 2013

Leave a Comment

25 Responses to “Heart over Heels”

  1. avatar

    Knockout dress and shoes. You look fantastic! But the right guy will love all your looks, no matter how fun and colorful. Maybe these bankers and doctors don’t yet have a sense of humor about these kinds of things…

  2. avatar

    How bout taking a trip to Malaysia. It’s summer all year round here! Get some vintage nyonya kebaya and see if you like the people here.

    On another note, joosy colours pleaaseee….

  3. avatar

    Congratulations lady, this piece is so funny, true and not to mention sassy!

  4. avatar
    Cindy Wolf Duffy - Reply

    hi natalie. i loved your blog today. i understand what you are going through, as i did as well for many years. i just wanted to tell you though, you are beautiful and you have great style and just a very successful life and career. i can only think these men are not off put by your style, but by your success and your independence and smarts. a man who analyzes and critiques the way you dress for a first date, is certainly not a man someone like you (or any girl for that matter) should be involved with. you never look anything short of striking in the photos i’ve seen you in and taste is a gift, and you have that gift, not to mention your other beautiful qualities. thanks so much for your blog. i do love it. i write http://www.eyecovet.com. i’ve featured you a few times. my blog isn’t to the caliber of yours, but it’s a fun and creative outlet for me for sure.


    ps-i met my husband on a blind date four years ago. we were set up by mutual friends. it was always my policy to never turn down a blind date. it can work, i’m proof! xo

  5. avatar
    shesaidsomething - Reply

    “Have I pressured myself to believe that doctors, investment bankers and all those guys with regular jobs.” This would be the problem in a nut shell. Bankers and lawyers? No thank you.

    I skew towards a mature, fashionable goth (I love black, head-to-toe with kick-ass shoes ;). I just cannot make myself into something I’m not (I mean I can be professional for my job – toned down mature goth ;). And although I have a killer sense of humor it is too sharp for some people and I’m just not that nice. Online dating is not an option for me.

    Where you put on the “dating Natalie” I would have to put on the “sweet” shesaidsomething. I just can’t be that person. I need a slightly dark, wee-bit-broken man in his early 40’s (with a f’-the-world attitude :).

    You need a creative type who enjoys a unique perspective. I suggest looking at more creative professionals, e.g. design (architecture, graphic design, etc.). Also, don’t worry about older guys. Go younger :).

    Oh, and get your friends to keep their eyes open ;).

  6. avatar
    Monroe Steele - Reply

    What an interesting story you have. I love your honesty. Lets face it dating in New York is really effing hard. Some guys just DONT GET IT. I think you should do what you want, dress the way you want, be free and be yourself and you will attract the type of man you want and that likes you “just the way you are”. I definitely think you ex was onto something. Great post as congrats on your feature.


  7. avatar
    pinkschmink - Reply

    I loved this column when I first read it in Vogue, and it’s just as brilliant second time around.

  8. avatar

    There is something incredibly depressing about a beautiful, intelligent, and creative individual reducing herself and the opposite gender to broadbase stereotypes and submitting to them. This is what happens when you only hang out with one gender.

  9. avatar

    It’s all about the coming attractions with men! They feed off of “possibility” and the outfit is the first indicator of that “possibility” way before personality comes into play. You don’t have to compromise your wardrobe in order for a guy to get it. Just adapt. I have outfits I would wear with my friends (although my guy, knowing him, would probably like it) and I have outfits that I LOVE wearing when I’m out with my man. Even then, his favorite items on me are feminine pieces, simple, but alluring. It’s just enough to juice up his imagination about how the night will unfold. That doesn’t translate to “tight and short”, (and whoever suggests that is disqualified IMMEDIATELY), it’s just something else. I think it really is simplicity and being comfortable in your own skin. Guys are really good at gauging that, whether they’ll admit it or not.

    I think your black dress is absolutely spot on for you…it’s flirty, sexy and alluring. A perfect combo for the right man to want to know more about you.

  10. avatar
    styleJess Je - Reply

    Congrats on your new VOGUE feature, Natalie! I adore hearing about your dating adventures. I even shared your video with Brad! ha Although you look smoking in your LBD, I think you would be happiest finding a guy who loves you wearing a Joosie outfit that is just, well YOU! Looking forward to hearing more, as always! xo

  11. avatar
    Christina - Reply

    Love this! And don’t change one bit, your true love will love you and your clothes! I met my husband when I was 35….

  12. avatar
    kKate McLeodKate McLeod - Reply

    I just don’t understand how a woman like you can say she hates musicals. You’re a fashion person. What is it about musicals? All that singing, dancing, great libretto get on your nerves does it? Revisit Guys and Dolls. That’s what I tell people who hate musicals. Just revisit Guys and Dolls.

  13. avatar

    Just a perfect pair of hip huggung jeans, a white t shirt and killer shoes… That’s the formula…. It works world wide. Very funny piece…

  14. avatar

    Gosh that was hilarious! I laughed at every rhetorical questions of yours. And that “it works visually” – exactly what I write for my Art transcription homework.

    I also have the School Bambam for the weekdays and the fashion Bambam for the weekends. When weekends come around, the accumulated desperation to follow my instinct in front of the mirror and the rapture from that is just out of control. Occasionally people realise, from Instagram, that there’s another me who finds herself in a whole different country over the two-day weekend. So you have precisely described what I’ve been undergoing indeed. My head just went pang, pang at every other word.

  15. avatar
    Clothes on Trees - Reply

    Oh how I identify with this! In my early 20s, all I wanted to wear on a date was a big, floral, farmer’s-daughter dress and huge red lips. I wanted to be myself, but the said “self” wasn’t sexy. I do not actually know how many women can say their tight-dress-skinny-heels persona is actually THEM – I never could. So my trick was to come in neutral – flattering jeans, a little cute top for example, and later, if the relationship holds, start pulling out the leopard prints and grandma’s scarves. I met my husband on vacation – where I wasn’t dressed as a fraud, but not quite like myself either. I think what mattered is my glowing skin, my relaxed appeal and my smile. Conclusion? Quit internet dating and go a trip? Perhaps?

  16. avatar

    Wow, great article.

    It must be difficult to fight your celebrity status and find men who don’t have pre-conceived notions about you (or what you should wear). I think this is a struggle that many, many women wrestle with — dressing for yourself vs. dressing for a man. I totally understand why you’ve felt the need to give them what they want (so to speak), but I also appreciate the fact that you are coming to accept the fact that the way you dress is a part of who you are and they can take it or leave it.

    Fashion does seem frivolous to a lot of people (many of whom are envious of you for your ability to look so adorable and happy all the time). but it’s no more frivolous or ridiculous than many men’s obsession with baseball and football and golf.

    Don’t let some stuffy investment banker make you think that your passion is silly. If he doesn’t understand and embrace your love for fashion, it’ll never work! You’ll have to bust out those crazy prints and headscarves and cat eye glasses sometime!

    Sorry for the super long comment… 😉

  17. avatar

    Why all woman wants bankers, doctors?
    They are so boring… Bankers have so much money, they can buy any woman and maybe sometimes they’ll really want a serious relationship but for sure this guy will cheat on you, in other words, they need a submission woman, that doesnt complains cause in the end they are paying for everything, and I think you are diferent… and the doctors? Oh God! They dont have time, and imagine if he’s famous… These kind might be our dream… but dont be mistaken, go for the simple ones, but you dont need their money, or even their status, you have already yours and life stablished, so try to look to the diferent ones… Just try!

  18. avatar


    “[T]he stuff of Kristen Wiig movies” — funny. Anyway, I have always thought your style is great, and you wear it well.

    All the best for 2014,


  19. avatar

    Wow, I loved this essay. So well-written and honest. I think this is an internal monologue that so many fashion women share–we want to dress for ourselves, but sometimes we feel pressured to dress for guys.


  20. avatar

    I am afraid your ex-husband was worth keeping. He loved you for who you are.

  21. avatar
    Katarina - Reply

    Hmm…I think that Jeff – if worth making out with – is the type of guy that could last in a relationship. The fact that you stopped dating him was definitely not the sweating – needless to say, you just weren’t that much into him. So no, it wasn’t Jeff, it was you. You are too old to be dreaming about the perfect guy. Nobody is perfect, we all come with our own flaws and strange habits. The day you are willing to oversee those flaws or habits you are in love.

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