Best Valentines Day Outfits over 50 to Wear When and Where (2024)

This guide discusses the best Valentines Day outfits over 50 for various plans. It covers what to wear for Valentine’s Day instead of red. Furthermore, the post addresses why and how to adjust your degree of sexiness to the length of your relationship, the place you go, and the weather. Tips include outfit inspirations for dinner, going to the movies, dancing, celebrate at a resort, just to mention a few. Finally, the post provides advice how to pick your outerwear for the commute to where you celebrate. 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. When you know why Valentine’s Day is associated with red it is easy to realize that red is an option, but not a Must.

Switch things up.

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 for a Valentine’s date over 50 than skin everywhere. Therefore, 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.

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.

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

Best Valentines Day Outfits over 50 for Dancing

When you are going to a Valentine’s Ball or dance partycheck 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 co*cktail 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.

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

What Outerwear to Wear Over Your Valentine’s Day Outfit?

How will you get there? If you have private transportation, you can go for hot sandals or pumps even in cold climate regions-pre-assumed you have a heated garage and can park the car in a heated parking garage at the venue. However, when you have to walk and/or wait for public transportation or park outside, 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. When you wear formal or semi-formal wear use the same strategies for thermal comfort like when dressing for a ball in cold winter weather.

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 when it is chilly in the restaurant). Well, when you plan to dance, have your dance shoes in your bag.

Tip: Always carry a huge bag to swap your boots for pumps whenever you come inside. Also you can have your clutch inside that bag.

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, have fun, and 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 guidefor inspirations.

Photos: G. Kramm

© 2013-2024 Nicole Mölders | All rights reserved

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