| What should I wear on a first and second date? | Hot Conversation |
I’m 52 (but look younger) and am re-entering the dating world since my divorce. What should I wear on a first and second date?
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I gave up wheat and sugar in my early twenties and except for social occasions where pizza or pasta or birthday cake are served, or the long hike that earns me a piece of chocolate, I've stuck with that plan. I'm not a naturally lean person, which 
Evie and Doris, I'm so with you on this. My dad used to say, "Family is everything," but when he died, so did the family. Or, to apply the loveliness of the Holmes poetry, after horrendous abuse, I just drifted away. Family is an accident of birth. L
Hi Doris,
I am a lot older than you and can only tell you my feelings, around family, as I've aged.
My childhood was rough and my parents made so many mistakes, alcoholism, neglect, etc. For many years I resented them for giving me such a poor Thanks Barbara, I guess the constant rejection applying for phlebotomy position really got me down.I am researching working as a medical esthetician that would get me out of the Spa but I would still be in skincare. Also I have 26 years experience as
The toughest part for me, as an adult who has put my difficult childhood behind me, is dealing with family members who are in denial about anything being amiss about how we were raised and the impact this has had on our on-going relationships.
W
Hi Debbie,
Sherrie makes many good points. Clothes support the message, but remember they also send a message that can enhance or detract from who you actually are, and what you’re actually saying.
It also depends on your age, lifestyle, profession, and city of residence. But you always want to look polished and classy, as long as it’s also appropriate for the occasion. A pantsuit looks wonderful for dinner and a show. Remember that you want to dress true to who you are, but dressing well is also a sign of respect to those around you.
Choose vibrant colors like royal blue, true or ruby red, or magenta to wear close to your face. They will make your skin glow and give you a youthful look. Be sure to put the focus on your face, though, by wearing a red/orchid/plum lipstick – whichever best flatters you, and bold earrings. Silver earrings tend to look better than gold, as gold can overpower the face.
Avoid provocative clothing – you want your date to focus on your conversation after all! But most of all, have fun, enjoy this new adventure, and remember that the way you dress announces the way you feel about yourself. Others will see that and treat you accordingly!
Enjoy!
Sandy Dumont
THE Image Architect
http://www.theimagearchitect.com
A first date can be a fearsome endeavour. Confidence is such a crucial element on a first date – or any date – or just in general.
Do you have something in your wardrobe that flatters you-that makes you feel good about yourself? The cut, the color, the decoration? Is there something that you put on whenever you want to look unique/special? When you’re on the dating market, remember that you are competing with a myriad of other ladies – if you have something that sets you apart, then for goodness’ sake WEAR IT.
What I do, is wear an outfit that is pretty basic, or mildly retro, and then amp it up with jewelry, scarves or patterned hose, etc. Light up the basics, if you like.
However. As the answers before me have said, you do not need to do anything excessive, or foolish. Heels that are stylish but too high to walk in; blouses so low cut you can’t lean over for a second helping of BBQ (or whatever) will make you uncomfortable, to say the least.
In many ways a first date is like a job interview. You want to wear something that puts you at ease, but will set you apart. On the other hand you don’t want to wear anything dour, (who knows, your date might have the attention span of a lemming) or too tight/short.
Amazingly, dates are actually supposed to be fun. And what could be more fun than going out and Knowing that you look fabulous, and beating the ladies at their own game?
I say a good bra for when you’re approaching and a good shaper for when you’re walking away.
WOW First date huh ? As I’m on my third husband with a major dating history, I am qualified to answer this ! Date 1 He is still auditioning so cover up but show your shape in a fitted little dress ( anything from a little Milly or Rebecca Taylor number to Banana Republic;and heels.You want to look modern and take control. Date 2 ( if he makes it this far ) wear skinny jeans and a silky draped top, and boots or heels. By date 3 you can lose the heels and add a V neck cashmere.
I thought Sherrie made some excellent points. For me, it all boils down to her #5 point: be comfortable and confident. If you look in the mirror and don’t see your authentic self…change your clothes. And have fun.
All good answers above – be sure whatever you wear is appropriate for the occasion, don’t be a frump, but avoid the excessive, “trying too hard” syndrome.
Oh gosh. Reading these responses made me feel that I am not in the dating game, as I have been married FOREVER. But–if I were, I too would vote for comfort above all. And if the guy can’t handle that, too bad for him.
Wow! so many good suggestions. I will be entering the dating scene this summer. I think that I look older than what I am, currently terribly out of shape, (working on it though), and scared whitless. I never really dated, (past history) so I don’t have a clue of where to begin. After 7yrs I’m going to give it a whirl. Thanks for all the great advice. I will go shopping for a nice little black dress and patterened nylons. A good bra, and a shaper for the rearend! Plus keep up the new workout routines (including the Kegals).
Good luck. We think that you need to dress to acctract the qualitities that you are searching for in a man, and dress to your highest standards. Are you a neat and fun person? Than your clothes should reflect that! If you are more creative? Make sure your not hiding the real you under a safe and boring outfit!
If you want actual current outfit solutions, you might want to check out fashion some over 40 fashion sites, like:
http://www.fashionforrealwoman.com or http://www.fabulousafter40.com
More magazine is also an excellent source of inspiration!
I am delighted that a publisher finally came out with a magazine geared toward mature women. Though most fashion is fun, a lot of it is geared to the younger set.
I’m 51, and what seems to work best for me at least, is what I like to refer to as casual chiche. An example would be be a skirt or pant that fits well, but not too tight; it would look nice with semi-tailored tops/jackets and a piece or two of quality costume jewelry or the real stuff. I’m a big believer in aging gracefully.
I might add to get in line for the book:
by Lisa Daily. I’ve read it and it’s very insightful and hilariously entertaining!
I wish I had the benefit of your photo or knowing more about you . Besides your age, these are really equally important factors in dressing well. Physically and as personalities–we are all unique-and I think we should celebrate and appreciate that–especially as you approach a fresh start.
I might assume you look like you are in your forties, and that may be because you are, and look fit –and have taken care of your skin.
Still there are some basics I would advise.
1. Dress simply and modern– definitely feminine—and appropriate for where you will be going (a movie or is it a high-end restaurant?).
2. Avoid being too overtly seductive (very tempting for many women when it comes to pleasing men), gaudy with excessive bling.
Choose well fitting, quality clothes that are not too tight or too loose, not revealing too much cleavage, too short or too (frumpy) long a hem on a dress or skirt, etc.
It’s so important to remember — yes, you want to look attractive– but not overly eager and insecure. Your outfit should assure the focus is on you as a person.
3. Wear clothes that highlight your strengths and detract from your less attractive physical attributes (i.e. some women look great in a knee length skirt–but some look better in slacks or jeans).
4. Wear jewelry selectively—less is more.
5. Be comfortable and confidant in the outfits you choose. First dates should focus on rapport and mutual conversation — clothes are always meant as a second language that supports the message you want to give.
Best,
Sherrie Mathieson (www.sherriemathieson.com)
In doubt about what outfits flatter YOUR body? I strongly recommend taping and watching several episodes of “What NOT to Wear” on TLC. Clint & Stacy’s advice and practical tips have been invaluable to me, a 53-yr.-young divorcee who has been in and out of the dating scene for many years. I dress confidently (not shlubby) every day, despite my extra weight (40 lbs. more than my wedding day), and everyone remarks that I look much slimmer than the scale reveals! From WNTW, I’ve gained the confidence and clothes that flatter my bigger bust and hips, creating a curvy shape that ALWAYS looks better than a BOX! Real men love curves, ladies… learn how to show them off! Kelly in Reno
I was/am interested to see the answers to this question. I haven’t had so much as a coffee date in several years. But, my daughter & a friend of hers are insisting on introducing me to someone – with the 6 of us going out to dinner.
I am 64 but most people comment that I look more like I’m in my mid-50′s. I am about 15 #’s overweight, but have been working on weight loss & hope to get at least a couple more off before the date in about 2-3 weeks. I wear my make-up well & am very comfortable with my short hair style.
Because of my work situation I’m able to work in very casual clothes. I do have some nicer things, but more in the Spring/Summer line than the colder weather wear. I certainly know how to dress appropriately for my age – stylish not frumpy; and, I don’t normally ever wear excessively revealing clothes. But I believe in being real.
My apprehension about this is the fact that this man is a physician & I truly do feel intimidated about that. I guess my self-esteem is my issue. So, I’ll need help to be certain & increase my confidence level by believing that I look nice. I also know that where we go out for dinner will dictate somewhat to my attire, but hope that it won’t require a dress. I haven’t worn a dress in a REALLY long time. So, I’m guessing this is going to require a shopping trip – which I do not really enjoy. You know how when you really need something specific you can never find it? UGH!!
Good luck to you Debbie – please wish me luck too!
Being intimidated because he is a doctor is a real bad way to start a relationship. Trust me, doctors are human beings just like every body else - my last boyfriend was a surgeon and was nothing to write home about. Some are nice, some not. Some are good husbands and fathers, others killers and abusers. Look at the nice qualities you are bringing to the table and see if he is worthy of you.
It would naturally depend on where you were going. BE outrageous and have fun. If he can’t take it, oh well. At 50, we are still asking what to do and wear with men on dates?? That might be more of a concern for a man than anything you could possibly wear.
I totally agree. I wear what I want and if they don’t like it thats to bad. At 50 we sould know how to dress for anything. Right?
You would think so, but there are a LOT of sisters out there who could use a makeover/update. We do not want to be “mutton dressed up like lamb”! I work at a hospital clinic and you would not believe what some women (and men too) wear when they come in for their appointments. Not everyone is a “fashionista” but they could at least be CLEAN, brush TEETH and comb HAIR!
Dress for who you are. If you are sophisticated, dress accordingly, albeit not over the top. If you are more casual, dress casually, without wearing your old sweat shirt. In other words, don’t play games(with your clothes) and pretend to be what-who you are not.
I am in my 50s, a widow and have have been in this dating situation. I was dating a retired gentleman and decided to dress up but not overdo it: I wore a blouse, black slacks, sheer black knee-highs and open-toed pumps with a 2 in block heel. It lead to several other dates where I wore a dress. pantyhose and boots.
LOVE all the comments and practical suggestions – nice to have all this free advice=:) I am a VERY youthful looking widow and have been dating a widower who’s a few years younger than me for nearly 2 years. We have known one another for close to 20., so he’s seen me in all sorts of situations (and outfits ranging from sublime to ultra-casual) I always have loved clothes and dress well(I am a retired professional post-secondary educator) The challenge now is to look pulled together and modern in more casual clothing. I remember our “FIRST REAL DATE” – it was my 60th BD and he had asked me to dinner at a very upscale restaurant. Agonizing over what to wear, I ultimately chose what made me feel great, and his compliment of “knockout!” when he came to my door gave me a huge boost=:) I hope you will have 2nd, 3rd & innumerable dates to come, and as things develop, you will relax as I did. Whenever we go anywhere, I always try to look my best, but my heart sang the day I heard him say. “It’s not what you wear, it’s who you are….” I had the flu and met him at the door in my jammies as he delivered a “care package”! But there is one clothing trick you may want to try after you’ve dated awhile. Whisper quietly to him, in the restaurant, at the moves, party or wherever, that you’re wearing sexy black lace panties (or no panties) under your clothing and see what difference that makes to your confidence & fashion sense =:) GOOD LUCK & HAVE FUN!!!!
I am new to the site.
I am a certified Coach. The clients I plan to coach are precisely like you, Debbie-divorced, age 50′s and 60′s
Fifty two is a wonderful age and so are the 60′s. Turning the corner at the end of the sixties requires mental work.
My advice to you is relax. 52 is sooo young . Forget the numbers.
Sit down and think back to a time when you felt so good about yourself, you can recall it even now. That is who you are- pull it out and start living into it . Your shoulders will go back behind your ears.Your muscles will tighten up and
you’ll be in charge again.
Find a new hairdresser-avant-garde,uplifting.
One way to help decide on a new wardrobe is to tryout with Personal Shoppers in good stores . You don’t have to buy from them if you don’want to. They will give you ideas about what You want. Try a few.
Men want to be liked and thought well of and doctor’s are no different. They are snsitive like all of us, mostof the time!
Have Fun!
Helen
The last and most important piece is! “Your thoughts create your reality”
Decide who you are and what you want and go for it.
H.