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Ptermann knit dress, smoky quartz belt, leopard print Fendi boots, leopard print tights.

This guide discusses the best Valentines Day outfits over 50 for various plans. Get ideas what to wear for Valentine’s Day when and where. Read to get inspired.




What to Wear for Valentine’s Day the Modern Way

The big question is What to Wear. As so often in life, there is not one hard answer. First of all,


Ditch the old-fashioned rule to wear red on Valentine’s Day.

Red seemingly adds weight! Of course, you can wear red when you can afford the illusion of a couple of extra pounds. More on why Valentine’s Day is associated with red. Red is an option, but not a Must.


post logo for best outfits for Valentines Day over 50 showing a woman in red slip looking worried


Switch things up by wearing pink instead of red.


Tip: A LBD with the right accessories and cut is always appropriate.


On Valentine’s Day, one can say the same for the little red dress (LRD).



How Long Do You Know Each Other?

If you just started dating or it is your first date, go for more coverage. A knee-long long-sleeve fitted crew neck LBD or LRD with tights is perfect. It showcases your body without looking over-the-top sexy. You don’t want him to stare at whatever. You want him to look into your eyes and talk with you so you get to know each other better.


Tip: Less skin leaves more to the imagination.


If you know each other for quite a while, you can show more skin. But one area at a time is so much more sexy and attractive than skin everywhere. Thus, either a mini skirt or cleavage or shoulders, not all at once. Recall you are celebrating your relationship.


Your goal should be to put together an outfit that highlights your best feature or shows your shape in an understated way.


More on how to look sexy for a Valentine’s date over 50.


Consider Where You Will Go When Picking Your Best Valentines Day Outfits over 50

What to wear for Valentine’s Day also depends on the weather and where you go. For instance, when your plan is to go to the movies, a casual look is best. Like skinny jeans, a wrapped top, motorcycle boots, and a slouchy cardigan, or a cute belted floral print dress that just shows your collar bone and ends above the knees with a cardigan.

Going to a restaurant means you can dress up. Keep the dress code of the restaurant in mind when picking the outfit.


Be aware that in very casual places, anything remotely sexy will get you irritated looks and may even make you and your significant other feel uncomfortable.


Instead of showing any cleavage, try an animal print and a pencil skirt like the the outfit below. It is modest, a warm winter outfit, but snake print and a pencil skirt have something sexy to it without being right into the face.


3 Valentines Day outfit ideas for a casual dinner or going to the movies
V-Day outfit inspirations without and with red for a casual plan like going to the movies, a casual restaurant or winter sports resort dining room, drinks at a sports bar. Left: J. Crew snake print pencil skirt, GNW cashmere merino wool sweater, statement bell for shape, Söfft shearling booties, smoky quartz floral statement belt, tourmaline earrings, GNW semi-sheer pantyhose. Middle: GAP sheath dress accessorized with two DIY brooches and a Judy Gum brooch over GNW Luxe cashmere wool sweater with GNW tight, and Harley Davidson booties. Right: Manalo Blahnik booties, GNW tights, G-III skirt, LandsEnd sweater, Halftee layering lace top, pearl necklace, Hermes bangles.


In cold weather, deep cleavage in the front or back would look like you are desperate.



Outfit Inspirations for What to Wear Where for Valentine’s Day

Shop your closet for items similar to these depending on your plans.


Casual Dinner or Going to the Movies Best Valentines Day Outfits over 50

style book author in red knit dress for Valentine's Day with leopard boots, gemstone belt
Road houses, casual restaurant or winter sport resort restaurants have a casual, cozy, sport-inspired dress code. Take it up a notch with a statement piece like the belt. Peterson knit dress, Halftee layering top, Hipstik tights, Manelo Blahnik leopard print boots, Rebecca Collins belt, DIY earrings, Festina watch, and Hermes collier de chien bangle.



causual outfit inspiration for V-day in warm climate regions
Going to the movies or a casual restaurant in warm climate regions. Left: eShakti Little Red Dress with floral silk scarf, collier de chien belt, and Calvin Klein pumps. Right: Landsend cashmere sweater, silk scarf, Oliveo pleated leather skirt, Hermes collier de chien bangle, DIY bangle, gemstone necklace, pearl studs, upcycled boots, Halftee layering top and tights c/o Hipstik® Legwear



Best Valentines Day Outfits over 50 for Dancing

When you are going to a Valentine’s Ball or dance party check the dress code. If it is formal or a  military ball , go for a gown, not shorter than knee-length. If it says semi-formal, a long gown could be over-kill. Go for a cocktail dress. In case of a social dance, a fancy fit-and-flare dress with or without some red will do the trick. Informal or casual? The best Valentines outfits over 40 are metallic pants or a sequin skirt with a cute top, or (white) jeans with an embellished or sequin top.

Is there a theme? If so, stick to it, and you are out of the salad. For a Valentine’s social dance with a romantic theme, stick out of the crowd with a floral print dress without red like the blue and white one below. It is very modest, but features your boobs, and legs without having a mini length hem.


best Valentines Day outfits over 50 for different dance events
Left: Romantic outfit idea for Valentines Day Social Dance. Middle: Semi-formal dance event. Navy sequin black velvet sweater dress c/o AMICLUBWEAR, and Very Fine Dance Shoes Latin dance sandals. Right: Going out dancing at a bar. Neo Tango shoes, Cuddle Doo top, BCGC belt, and 7 layers tulle skirt.



Valentines Day outfit idea for a formal event in a hotel’s ballroom




Outfit idea for a semi-formal V-Day dance in a hotel’s ballroom


maxi dress as an example of what are the best Valentines Day outfits over 50 at a resort
Warm climate vacation resort: Unbranded maxi dress,  necklace c/o Happiness Boutique



How Will You Get There?

If you have private transportation, you can go for hot sandals or pumps even in cold climate regions. However, when you have to walk and/or wait for public transportation, you should choose a pair of shoes that provides good insulation from the ground, but allows to safely walk even on snow and/or ice.

Also wear a warm coat. When your indoor outfit is made of thin, delicate fabric have a light cashmere cardigan that you add for extra insulation (or as a cover-up in case it is chilly in the restaurant). Well, when you plan to dance, have your dance shoes in your bag. I always carry a huge bag as I have the habit to swap my boots for pumps whenever I come inside. Did I mention that there is also a clutch inside that bag?

I know, I know! It’s an Alaskan lifestyle thing.


Anyhow! If your boots or booties are needed because of the outside conditions, bring the strappy sexy sandals or pumps in a large bag or tote. It is so much better than freezing your toes off.


Remember goose bumps are never in style.


Most importantly avoid these mistakes when dressing for Valentine’s Day.


P.S.: Are you still looking for Valentine’s Day gifts? If so, also check out my gift guide for inspirations.


Photos: G. Kramm

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