Holiday Dressing

10 Ways to Dress Sexy on Valentine’s Day Without Letting it All Hang Out

boomer couple romanticAre you going out for a romantic Valentine’s Day dinner and want to look sexy without letting it all hang out?

Here are some tips on How to Dress on Valentine’s Day to look alluring at 40, 50, and beyond.

1.  Reveal a little Skin

Don’t make the mistake of wearing a  turtleneck on a date if you want to look sexy. This kind of coverage signal stays away! Showing some skin is youthful and alluring. But notice, I said some.

Trying to look sexy by dressing in skimpy clothes that a twenty-something would wear clubbing will make you look hard, tacky, and worn out. On the other hand, you don’t want to look dowdy. So, where’s the middle ground?

How to Dress Sexy on Valentine's Day Red Dress


To look sexy, not sleazy or silly, all you need to do is reveal just one part of your body. This will make you look mysterious and alluring. There are many sexy Valentine’s Day dresses, but remember, a sneak peek is better than a striptease!

For example, if you have a nice bust, try a low-cut V-neck top, but don’t try to wear a miniskirt too. Instead, opt for a regular skirt, like a knee-length pencil skirt, and keep all the focus on your neckline. It’s all about balance. You don’t have to wear a top cut down to attract your man’s attention.

A cold shoulder top or a top that is slightly off the shoulder will give you lots of sex appeal. Your shoulders are sexier than you think and are a classy way to look alluring after 40. A slit or zipper on a skirt is also sexy.

2.  Fight the Tight

The famous Hollywood costume designer Edith Head once said: “A dress should be tight enough to show you’re a woman and loose enough to prove you’re a lady.” That’s especially true as we age when too tight, too short, or too much skin can make a woman over 40 look downright desperate. It’s always nice to have a little mystery.

Resist the urge to wear tight clothes if you want to look sexy. Your clothes should be fitted but shouldn’t look or feel tight.  Stop obsessing about size tags. If you’re a size 10, forget about trying to squeeze into a size 6 or even an 8.  Tight clothes make you look bigger. You need to wear things that skim your silhouette and have some stretch. Looking like a stuffed sausage is not sexy at any age.

3.  Embrace Stretch and Drape

Soft, stretchy fabrics will flow over your figure and flatter your shape. Wrap-style dresses made from soft silk or jerseys always look sexy. The gentle wrap detail hugs your waist, lifts your bust, and highlights your curves. This red dress, shown above, is a great example.

4.  Wear a Soft, Sensuous Sweater

A delicate cashmere sweater or soft, feminine knit dress is another way to look alluring. Their beautiful texture makes you look like a fluffy kitten and makes your man want to reach out and snuggle you. Cozy fitted sweaters are another type of sexy Valentine’s clothes that many women don’t instantly think of.


How to Dress Sexy on Valentine's Day - Wrap Sweater


5.  Get Edgy with Leather

With its raw edge, Leather signals power, passion, and excitement. Wear it in moderation, not head to toe, or you will look like a geriatric dominatrix! Colored leather is easier to wear than black and looks sexy and modern. A leather jacket worn over a feminine floral dress is flirty and sexy.

 6. Animal Prints Bring Out the Tiger

Put a little tiger in his tank with a touch of the wild. Any animal print, like an animal print scarf or pair of pumps, is enough to get him roaring.

7.  Shiny and Sparkly is Sexy

Shiny or sparkly fabrics allow you to dress more modestly but still convey a seductive message.


How to Dress Sexy on Valentine's Day - Silky Blouse

8. Ruffles are Romantic

A slight ruffle is a beautiful way to whisper you’re interested. There’s nothing more feminine than a flirty frill.  A top with a scalloped edge is also very feminine.

9. Slip-On a Sexy Shoe

Heels are always sexy because they elongate your legs and accentuate your wiggle, but they don’t have to be crazy sky-high to be sexy. A small, slim kitten heel is also very inviting.

The vamp of the shoe also makes a difference. The deeper the shoe’s cut, the more skin shows on the top of the foot, and the sexier the shoe. Have you ever heard of toe cleavage? It’s a great way to look alluring in a subtle, grown-up way. It’s a great way to look sexy that you may not have thought of.

10. Try A Smokey Eye

Adjusting your makeup can make you more alluring; just try it and see. The eyes are the mirror of the soul, so why not try that dark, smokey eye you’ve been reading about to add a little mystery? A dark kohl liner and smudging make you look more passionate and playful. Keep the rest of your makeup, lips, and cheeks soft so your eyes take center stage.

For more great tips on how to look lovely on February 14th, check out these other Valentine’s Day Dressing Tips. And remember, confidence is your best accessory!

What will you be wearing this Valentine’s Day? Let me know by commenting below.

Visited 27,101 times, 1 visit(s) today
Join the Conversation

27 thoughts on “10 Ways to Dress Sexy on Valentine’s Day Without Letting it All Hang Out

  1. Great information!! Question though. Can a black dress be worn to Valentine’s cocktail party? What color shoes and accessories should I wear?

    1. Hi Kel,
      A black cocktail dress is acceptable for Valentine’s Day.
      You could wear black, nude, gold, or burgundy heels (I have a pair of burgundy heels in this post I would wear with a black dress:
      Bags- you could go with a gold, blush, pink, or red/burgundy colored clutch.
      No right or wrong, but these available colors would go well together for a Valentine’s Day theme.
      Have fun!

  2. I’m not a wrap dress girl because I have an apple shape plus a big bust, but I like to wear something more glamorous for a night out. I find you can look sexy with accessories too. My husband is glad I put on some make-up, did my hair, and got out of yoga pants!


  3. Unfortunately, I will be wearing a brown uniform on Valentine’s Day. I agree confidence is a women’s best accessory. My general rule of thumb for dressing myself is pairing a looser top with a fitted bottom (sweater dress with leggings) or a fitted top with a more flexible bottom (tank with a maxi).

  4. Debra, Great article. I thoroughly enjoyed reading these ten tips. Each one is beneficial for any given date night. Thanks for putting these together.

  5. We read more into clothing choices than men do. Leather? Mine says no way! A little skin, show your figure a bit, be tasteful, and dress appropriately for the occasion. Animal prints – lost on most men, I think. Yes, yes! A little scent, maybe, but just a little. Mostly be comfortable in your (well-cared-for) skin. Confidence is the best accessory! Nice lingerie is a close second.

  6. I would also like to add that women at any age should 1) play up their best features and 2) make sure to be comfortable. For a special occasion, don’t go with anything you’re not 100% at ease wearing. You can always wear sexy jeans and a great top dressed up with sexy high heels when in doubt.

    1. Hi Budget Chic, Right on!!! But the fit is essential for all types of bodies! We see many women with significant figures hiding behind baggy clothes and, of course, vice versa as well… the Main thing is to have the fit skim your body, not too tight and not too loose like you mentioned…
      But we like to go “the extra” regarding make-up, hair, and accessories. It all goes together to look extra nice!

  7. Deborah, recently you posted that red jeans are a big hit on your client’s lists and their wishes for Valentine’s day. I found some red jeans and got the sweater they showed, but what are you seeing that looks great with red jeans? They are “attention grabbers” on their own! Thanks, Jan

    PS Got the ebook on Chic on the Cheap and loved it. Thanks for the valentine’s day sale!

  8. Thumbs up for this post! It covered almost everything each girl should know before Valentine’s date. After following these tips, your man will be pleased to see a glamorous woman.

  9. My hubby and I are celebrating our 19th wedding anniversary on Valentine’s Day and I’ll be thinking of what to wear and not to wear so these points helped-thanks!

    1. Hi Nanne, Good question…Do men really like animal print? Probably depends on the man. You should ask them! We have to dress for ourselves first. Animal print really just says, “I’m a little wild!”… so if you do just a touch of it, like just a shoe or a scarf or a purse (one at a time!) then it can be super fun! When worn in large doses it goes a little too in your face.

  10. With my man, sexy is me in my Blue Jeans. Nice fit, nice curves…. a little cleavage and we’re good to go!

    1. No. It looks terrible on anyone. I think 18-year-olds look as desperate as 40-year-olds who wear too skimpy and tight clothes. You might be firm at 18 or 20, but you will still look cheap and tawdry.

It's your life. Make it Fabulous!

This error message is only visible to WordPress admins
There has been a problem with your Instagram Feed.