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Sweet? Sexy? Somber? First Date Fashion Flubs


As this blog gains readership among stylish senior women searching for senior men, I am frequently asked: What should I wear on a first date? Sometimes the question can be in the form of a plaintive cry, as from the widow who confessed it’s been 50 years since her last first date, to which event she wore a poodle skirt with crinoline underpinning.

Fashion is the fastest form of non-verbal communication, and what these women are wondering is:  What message am I sending when my senior man date sees me for the first time?

The average old guy will be unable to recall the details of your ensemble, unless it is gaudy, foolish, or a replica of something his ex-wife frequently wore.  He will remember his visceral response to your “look” – the sum of your hairstyle, clothing, jewelry, shoes, and smile.


How should you put yourself together for a senior man you barely know?  Can you be expressive of who you really are? Can you go wild or must you opt for the safety of conservative attire?

There’s no formula dress code guaranteed to jumpstart senior romance, not the least because the wardrobe choices of a tall, languorous redhead will be nothing like those of a petite platinum blond.  But here are some things to consider.

Cleavage Caveat — No matter how beautiful and well preserved you are, your décolletage is not the asset it once was.  Look down.  If you don’t see the gentle parting of two freckle-free symmetrical rounds — and if the last Bali you bought was larger than a 36C — wear something with a modest neckline.

Nice Like A Nun – If a man can’t glimpse some part of you that is uniquely female, he may reject you for seeming prudish. Don’t cover up entirely because your neck is crêpey and your stomach’s in a pas-de-deux with a layer of lard. You are not the sum of your imperfections. Your arms are firmer than you think. And your date, if he’s self-aware and therefore worthwhile, will be pleased with every part of you that’s real.

Boas For Boomers – If you’re meeting a Harley Hog greybeard, by all means wear your psychedelic headband and the muscle shirt that shows off your tattoo.  Other old guy types will respond more favorably to an outfit appropriate for luncheons in which arugula has a starring role. By all means be individual, but stay away from accessories that invoke circuses, dungeons, and bordellos.

Quothe The Raven – Black is a great camouflage, and a senior woman’s friendliest color choice, but too much of it is funereal. If you must wear black, confine it to your lower half and install some white or bright color next to your face.

Bijoux Beware – The majority of men, senior or otherwise, regard jewelry as emblematic of female silliness.  Ostentatious jewelry is distracting on a first date, and you will be wise to wear only classic, non-showy pieces — unless of course you are embarking on an early education program, letting him know that the gifting of baubles is central to your notion of romance.

Oh, Baby! – Your granddaughter looks adorable in her pink sheer mid-thigh skirt with an eyelet flounce. On you it will look majorly grotesque. The age limit for teensy skirts and belly shirts is about 19.  You needn’t wear white gloves, button shoes, and a cloche, but stick to age-appropriate attire, which in our case means something in which no human female under 30 would be caught dead.

Warrior Princess –Senior men mostly steer clear of a Clingy Clara, but they’re not looking for Athena, either. Put aside your black leather jacket with the chain mail trim and wear something quieter on a first date. Don’t be afraid of seeming too vulnerable. Far from being anti-feminist, vulnerability communicates openness, the promise of flexibility — and what could be more essential to making a senior relationship work?

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'Sweet? Sexy? Somber? First Date Fashion Flubs' have 11 comments

  1. July 4, 2015 @ 2:15 pm Trixie Pixie

    I try not to focus too much on what I’ll wear because it becomes and obsession with me. I can’t wear certain colors, i have to cover my bat-wing arms, not too much jewelry. You can drive yourself crazy.

  2. March 8, 2013 @ 4:00 pm My Inner Slut

    I dress sexy because that’s what men like, period.

  3. March 6, 2013 @ 11:44 pm rebecca

    It’s tough to get it just right. We have to act our age (I’m 66) but still be fashionable. I try to err on the modest side. No full cleavage, but hey, a hint is nice. Men are sexual beings, that we know. And body image counts for a lot. I find I hide things I don’t like about my body. For example, I know all about those freckles on the chest, but I have great legs so I almost never wear pants.

  4. October 8, 2012 @ 8:46 pm Elizabeth III

    My motto is “show your shape not the equipment”. Be fashionable but not crazy. Be feminine not trashy!

  5. December 31, 2011 @ 8:37 am Alicia

    I’m not sure a demure Calvin Klein suit is going to do it. Who are you dating, a priest? I find that men like something flashy and colorful.

  6. November 5, 2011 @ 1:49 pm Mary Gold

    This is easy for me. I always wear the same outfit, a Calvin Klein pants suit with a white blouse and pearls. It seems to work. I don’t like to call attention to myself with bright colors. I also wear low heels in case the man is not very tall.

  7. October 2, 2011 @ 10:52 am MG47

    Men really don’t care what you are wearing as long as it’s cleavage. But when I wear a scooping neckline I find the man is looking there more often than my face, and I think my face is nicer, really. lol

  8. August 19, 2011 @ 10:35 am MsPreserved

    Men do like red lipstick I guess a lot of them. I have been asked by men why I don’t wear red lipstick or they ask me flat out to wear it and what I usually do is put it on to show them how awful it looks. I look best in a nude shade and when they see the difference they are usually amazed and let me go back to my old way.

  9. June 19, 2011 @ 5:58 am TooShy2

    I agree that men don’t really pay much attention to what you are wearing unless it is something that calls too much attention to itself. But I disagree about the earrings. Men seem to like gaudy ones. And they like red lipstick. As for real jewelry, I don’t have any, so it’s no

  10. June 16, 2011 @ 1:31 am MaltaR

    I think this is the hardest thing about online dating. Not even figuring out if and when and where you’ll meet is half as bad as this. I usually wear something conservative, as you recommend.

  11. June 14, 2011 @ 1:51 pm Tracey

    I think you’re being too conservative. I am 58, 5’5″ 128 pounds. I am not afraid to show a lot of flesh and men seem to like it. You’re like a lot of women who are too obsessive about their bodies.

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