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What to Wear on Valentine’s Day…The Line Between Your Likes and His

Valentine’s Day is Friday and presents that challenge for many of us of what to wear, what to wear?

But, please listen carefully, this decision must begin with your own confidence in how you look each and every day.  I learned only ten years ago, that I must dress for myself first and have confidence in who I am and not rely on the approval of others to find joy.  Once we walk in confidence, strength and dignity, then we can have a rockin’ date night!

what to wear, date night, valentine's day, fashion for 50+ women, pencil skirt, wrap dress, midlife women

So, Valentine’s or any date night must walk that fine line (sometimes) between what we like and what we know they like!  This is the time I really want to dress for my husband of twenty-nine years, and I want to also feel confident in what I am wearing when we leave the house.

I am not going to wear something he wants me to if I do not feel fabulous in it!  I have learned his likes and dislikes over the years.  Sometimes he is very vocal, and sometimes his silence speaks volumes. As my outfit-of-the-day photographer, if he does not compliment the look, he doesn’t really like the look.  He does have good taste and prefers styles which are chic, classic, and have a fabulous fit.  Nothing wrong with that.  Actually, he is right when he points out that clothes which fit my curves are more flattering.

But, sometimes I am a little bohemian and love tunics and the Eileen Fisher-flowy-drapey styles. He does not want me to hide behind the larger garments.  He even balks at long necklaces because they stop over the pudgy middle and he says that calls attention to it.  I use to get hurt by these comments, but after growing in confidence and understanding my own style, I now receive them as constructive advice.  And, as I said, he is often right. (If he reads this, I will never live it down!)

Here are some pieces he would prefer to see me in for date night (links are affiliate links):

  1. A GREAT PENCIL SKIRT.  I seem to wear my black one most often, but I have seen some graphic black & white prints on the horizon for spring and it might be time to pick one up. Show the legs and the curves!  Also, I have discovered most men (not all) are not fans of colorful prints and really not fans of pattern mixing!
  2. A FORM FITTING SWEATER OR KNIT BLOUSE IN A SATURATED COLOR.  He gave me a beautiful silver and turquoise bracelet for Christmas and I always recommend we wear those gifts they give us in their presence!  I do have a sweater which looks like it was born to live with the bracelet. Turquoise and black have been a trend pairing this past year!
  3. A FORM FITTING JACKET–NOT BOXY–with SEAMING FOR THE CURVES.  Valentine’s Day might be the perfect time for a white jacket. You don’t have to wait until Easter, ladies.  Forget that rule!
  4. A SHEATH OR FAUX WRAP DRESS have the same effect as a pencil skirt.  The fit is plenty sexy enough. You don’t have to go low cut in front or back to be sexy.  You will be surprised how great this looks on a curvaceous figure.  (Test me–try them on.)  Another courageous step for some of us–show those arms!  Remember, if the night is just slightly cool, it is still romantic to wear his sports coat around your shoulders on a date!  Never too old for that!
  5. PANTS WITH A GREAT FIT. If it is too cold for a dress or skirt, wear pants which fit.  Mr. B really likes me in leggings or skinny jeans.  I just have to make sure the top is not too oversized or drapey, but the skinny jeans do look great with jackets!
  6. SIMPLE ACCESSORIES. Finally, for my husband, accessories need to be very simple…understated elegance.  I always note which accessories he compliments, so I can wear them when we go out.  He is not a fan of long necklaces or long scarves. They will stay home.


Well, what are the men in your life hoping to see on you this Friday?  Please share with us or if you have a fun outfit planned…tell us what it is!


No matter what you wear make sure you go out in confidence and joy.  Your smile is the best accessory!


Thanks for stopping by The Joy Boutique. May your Valentine’s week be full of hearts and flowers!

 midlife boulevard, columnist, midlife women, middle-age, midlife crisis



Pamela Lutrell

Pamela Lutrell began her blog, <a href="">over50feeling40</a>, July 2010 with a desire to encourage women over 50 to walk in strength, confidence and joy. Of course, head turning style makes each day fun!

Pamela Lutrell

Pamela Lutrell began her blog, over50feeling40, July 2010 with a desire to encourage women over 50 to walk in strength, confidence and joy. Of course, head turning style makes each day fun!

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A Quiet Corner

Thursday 20th of February 2014

My husband loves me regardless of what I wear...jeans and a turtleneck, a sexy red and black from White House Black Market, my flannel shirt and old jeans for yard work, my kayaking clothes, or one of my bathing suits I bring to Aruba...I still get his attention and that is LOVE!...:)JP

b+ (Retire in Style Blog)

Wednesday 12th of February 2014

My husband loves to buy me clothes and will even shop with me for them. He bought me a gorgeous dress for New Years Eve that surprised even me. It was a Ralph Lauren made out of spandex with folds across the front and a draped neck. It is very, very flattering! I think it makes him proud to see me looking confident and beautiful.

Good advice and I do love Valentine's Day!



Wednesday 12th of February 2014


Darlene Fadem

Tuesday 11th of February 2014

Great article Pam! My husband is all about romance and seeing me in something sexy. I, on the other hand am not into romance at all...or dressing sexy. Here is a link to an article I wrote for Valentine's Day showing my husband's fantasy versus my reality of what I wear.

Carol Cassara

Tuesday 11th of February 2014

All good advice. Especially "wear something he's given you."

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