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Banana Republic abstract floral print fit-and-flare dress, Very Fine Dance Shoes sandals, sandals, statement belt, Hermes collier de chien bangle, amethyst earrings (all own) and lace sleeves c/o Cami Comfidential

This post addresses the worst mistakes when dressing for Valentine’s Day. Read what they are and how you can avoid them to achieve ageless style and look your best when creating for your V-day date night look.

  1. What Are the Challenges of Dressing for Valentine’s Day for Women in Midlife?
  2. What to Avoid when Picking your V-Day Outfit?
  3. Wear Something Like This Instead
  4. Worst Mistakes When Dressing for Valentine’s Day in Conclusion


Disclosure: There are affiliate links in this post.


What Are the Challenges of Dressing for Valentine’s Day for Women in Midlife

Valentine’s Day can be a real dress challenge for women over 40. Yes, the winter temperatures are one part of the challenge. You want to be attractive for your guy and look sexy, but not cheap is the other. No matter where the two of you are going, there will be the 20 somethings with an overload of flesh. Thus, how to look attractive and sexy for Valentine’s Day to keep his eyes on you seems an overwhelming task.


post banner showing one of the worst mistakes when dressing for Valentine's Day


What to Avoid When Picking Your V-Day Outfit

Like so often when it comes to dressing successfully for an event there is not a cookie cutter solution. Many factors have to be considered to get it right. It often is easier (=safer) to start with the negative, i.e. what to avoid. Here is my list of the major mistakes (and why) and examples as needed to bring the points across.

  • Thinking that you have to wear red on Valentine’s Day. Actually, read the history about wearing red for Valentine’s Day to empower yourself not to wear red.
  • Wearing red if red is not a flattering color on you, you will not look to your best! Recall when you feel uncomfortable in your clothes, it shows. Moreover, be aware that red visually adds pounds. If you don’t need them, why adding them? The look below shows a chic chiffon with lace sleeves abstract floral print dress that shows off your shape and works at a fancy restaurant and bar as well as a social dance.
  • Thinking you can’t wear red as a red head.


influencer showing how to avoid the mistake of a flesh show when dressing for Valentine's Day
Front view of fancy dress outfit inspiration


stylist showing how to avoid the mistake of thinking you have to wear red
Outfit details: Banana Republic abstract floral print fit-and-flare dress, Very Fine Dance Shoes sandals, sandals, statement belt, Hermes collier de chien bangle, amethyst earrings (all own) and lace sleeves c/o Cami Confidential


  • Seeing the twenty something as competition and dressing like them with large cleavage and cut-outs is a big mistake. While they can get away with it (some of them would still look great in a potato sack shaped with a belt), for us over 40 less skin is (more) sexy.
  • A body conscious or too tight dress. It makes you look like trying too hard. A midlife tummy doesn’t need attention. Period.
  • Wearing PJs or sweat pants when you stay at home. There are many cute looks to try for a stay-at-home date night.
  • A super short mini skirt. It may even look trashy!
  • Wearing heels that you cannot walk in will make you look Old Lady, ridiculous, helpless, and not attractive at all.
  • Not making one of your best features the statement. You would look like not trying at all.
  • Over-bling. Jewelry should highlight, but not compete with your features. A short necklace can highlight your collar bones. So sexy!
  • Not dressing appropriately for your plans and the weather. When you walk to the restaurant and a blizzard is in town, you are better off to wear winter clothes that you would wear for date night. Recall gGoose bumps are never in style.
  • Wearing a dress that fails to meet the vibe of the place you go is a big mistake. You will feel uncomfortable. The outfit below works when going out for dinner at a road house immediately after work and you pull the blazer off. It also works when you have to walk several blocks in cold weather to get to a casual restaurant. Again take the jacket off inside. The look wouldn’t work when you go for a social dance party or the restaurant/bar of your hotel when you spend the day in a winter resort. In these place, a fancy, dressed-up look is expected.


style blogger in V-Day dinner at a roadhouse outfit
V-Day look for a casual restaurant in a cold climate region


older women in a Valentine's dinner outfit for frigid cold weather
Outfit details: Anne Klein red turtleneck sweater with black blazer, London Jean boyfriend jeans and Michael Kors wedge camouflage pony hair sneakers (all own). Take the jacket off at the restaurant as otherwise your outfit looks like an office look.


  • Not having a cover-up when wearing a cocktail dress. Goose bumps are nor sexy, nor attractive. Who wants to feel ice cold feet when cuddling?
  • Wearing the outfit shown in the photo above when temperatures are above the freezing point. Only when it is really, really cold, the red turtleneck will be seen as dressing with the vibe. Babe, it has to be frigid cold outside!


Wear Something Like This Instead

When going to a casual restaurant and you look stunning in red, a little red dress like in the next photo is fine in warm winter climate regions. However, you should carry a clutch, not a huge tote like shown here. Moreover, you should go for a bit more makeup than here to stay out of everyday style.


Fashion blogger in a little red dress
eShakti Little Red Dress, Madden lace-up sandals, Jaeger tote, Hermes Medor watch, Hermes collier de chien bangle, black pearl necklace (all own), and wooden watch c/o Jord


When you wear Romantic Style, try a pretty feminine dress that shows off a feature like here the collar bone. Wearing the look with a blush jacket underlines the feminine vibe.


over 50 years old fashion blogger in outfit for going out
BCDC statement belt, Halogen quilted leather jacket, GNW tight, abstract print eShatki fit-and-flare dress, onyx flower statement ring


Adding a red jacket instead makes the look more casual, nice for dinner in a road house or casual restaurant in a cold climate region.

Girly summer dress styled for winter weather with red cardigan
eShakti dress with knotted Moda International cardigan, GNW tights, Manolo Blanik booties and wooden watch c/o Jord


What about a variation on the Little Black Dress with a hint of red in form of a scarf or brooch?


When you liked the tips in this post, you will also love my style book How to Dress for Success in Midlife. Buy the book now.


Worst Mistakes When Dressing for Valentine’s Day in Conclusion

  1. Competing with the twenty something in form of a flesh show.
  2. Wearing (cheap) dresses and/or colors that don’t flatter you.
  3. Not dressing with the place and weather in mind.
  4. Wearing red when you fell “fat” in red.

Instead, remember: There is no peer pressure as your guy (hopefully) has no other sweet heard. Dress your best in location and weather appropriate clothing. Don’t go for a flesh show, leave something to his imagination – even when you are married for several decades.



You may also like to read how to dress for Valentine’s Day depending on your plans and length of relationship.

Have you already made plans for Valentine’s Day?

When you are interested in reviews of the newest trends, and fashion and how to turn them into personal style, to look to your best in midlife, subscribe to High Latitude Style. Deep inside you know when I can do it, you can do it too.


Photos: G. Kramm.

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