You are currently viewing Best Valentine’s Day Outfits to Wear for Your Plan
Lula Roe full skirt dress, Coolibar sleeves, fishnets, Very Fine Dance Shoes golden sandals

This guide provides ideas what to wear for Valentine’s Day for various plans. Read to get inspired.

  1. Valentine’s Day doesn’t mean you have to wear red
  2. What to consider when picking your look
    • Where will you go?
    • How long do you know each other?
    • How will you get there?
  3. A little black dress is always appropriate
  4. Beautiful Outfit Inspirations for What to Wear for Valentine’s Day


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What to Wear for Valentine’s Day the Modern Way

Are you astonished or curious why the featured photo doesn’t show a red dress for Valentine’s Day? Well, first, red gives the illusion of more weight. Women in midlife don’t need that illusion. Our words have weight enough. Second, it’s old fashioned. Who needs that? Read on how to dress for V-Day the modern way. Sure, you can wear red when you can afford the illusion of a couple or two extra pounds. Third, there is no real reason why Valentine’s Day is associated with wearing red.


post logo what to wear valentine's day showing a woman in red slip looking worried


Valentine’s Day Doesn’t Mean You Have to Wear Red

I hope you have already an invitation or will get one soon. The big question on such a big day is What to Wear. As so often in life, there is not one hard answer. Here some thoughts on what to consider when dressing for the big night out. First of all,

Ditch the old-fashioned rule to wear red on Valentine's Day. #Vday #vdayoutfitideas Click To Tweet

Learn more about why Valentine’s Day is associated with red, and you understand that red is an option, but not a Must.


lifestyle blogger in casual red knitdress with belt and tall boots for Valentine's Day
Front view of red dress outfit idea


zoom on gemstone belt and leopard boots
Zoom-in on belt and boots for details


over 50 years old Alaskan woman in a little red dress with tall boots
Side view of red dress inspiration


stylist in red knitdress for Thanksgiving with leopard boots, gemstone belt
Outfit details: Peterson knitdress, Halftee layering top, Hipstik tights, Manelo Blahnik leopard print ponyhair boots, Rebecca Collins belt, DIY earrings, Festina watch, and Hermes collier de chien bangle



What to consider when picking your look

Where will you go?

Going to the movies, for instance, is a casual date. Your goal should be to put together an outfit that highlights your best feature or shows your shape in an understated way. For instance, 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. You can never go wrong with a LBD with the right accessories. On Valentine’s Day, one can say the same for the little red dress (LRD). 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 exotic and sexy to it without being right into the face.


stylist in modest winter look with sexy pencil snake print skirt

stylist in sexy pencil skirt and modest sweater for V-day
J. Crew snake print pencil skirt, GNW cashmere merino wool sweater, statement bell for shape, Söfft shearling booties with 4 inch heels, smoky quartz floral statement belt, turmaline earrings, GNW semi-sheer pantyhose (all own)


Are you going to a Valentine’s Ball or dance party? Then 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. If it is a social dance, a fancy fit-and-flare dress with or without some red will do the trick. If the dress code is informal or casual, metallic pants or a sequin skirt with a cute top, (white) jeans with an embellished or sequin top are good bets.

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 that is not featuring red like the blue and white one below. It is very modest, but features your boobs, and legs without having a mini length hem.

Less leaves more to the imagination. #dress4success #timelessstyle Click To Tweet


over 50 years old dancer twirling in a blue and white dress
Outfit details: Cat cameo pendant necklace, cameo earrings, Lula Roe full skirt dress, Coolibar sleeves, fishnets, Very Fine Dance Shoes golden sandals


But wait! Before you pick your dress, consider the following.


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.

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.

influencer in floral print dress with white top and long sleeves



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.


A Burberry coat is a great investment for women over 40
Zoom-in on details of the coat styling


fashion over 40 Burberry coat with scarf, gloves and beret
Outfit details: Burberry loden motorcycle coat worn over the above outfit with Harley Davidson booties, structured bag, blue leather gloves (similar here), blue paisley scarf and blue beret (all own)


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 like shown in the outfit photo. It is so much better than freezing your toes off. Remember

Goose bumps are never in style. #agelessstyle Click To Tweet


A Little Black Dress Is Always Appropriate

You don’t like red and you wore the LBD last year? Switch things up by wearing pink instead of red as I did in the post’s inspiration photo. The outfit shown in this post would work well with a red instead of the pink sweater for a Valentine’s day dinner with my husband in an Alaska Roadhouse heated by a woodstove on a -20F (-29.9C) day. Note that at such outside temperatures, it doesn’t get warm enough inside for deep cleavage in the front or back. Any cleavage would look like you are desperate.


jewelry over 40 brooches
Zoom-in on brooches


fashion blogger in black sheath dress over pink sweater
Outfit details: 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 (all own)


Don’t let the right outfit be a random thing. Wear the right look in every situation by looking up what to wear when in How to Dress for Success in Midlife. Buy my book now.


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

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

midlife stylist wearing silver pants for V-Day at a sports bar
Dinner at a sport bar: Silver leather pants, Kieselstein Cord belt, statement snake tail buckle, GNW Luxe sweater, Puma sneakers, and India Hicks scarf c/o Tammy Gray


40+ woman in a red tulle skirt as example for what to wear on Valentine's Day
Going out dancing at a bar: Neo Tango shoes, Cuddle Doo top, BCGC belt, and 7 layers tulle skirt


style over 40 Woman in a Little Red Dress for Valentine's Day
Going to the movies in warm climate: eShakti Little Red Dress with floral silk scarf, collier de chien belt, and Calvin Klein pumps


fashion blogger in suede red skirt with lace under sweater


over 50 years old fashion blogger in V-day winter outfit Casual restaurant: Landsend cashmere sweater, silk scarf, Oliveo pleated leather skirt, Hermes collier de chien bangle, DIY bangle, gemstone necklace, pearl studs, upcycled boots, layering top (all own) and tights c/o Hipstik® Legwear


style blogger in sequin velvet semi-formal dress
Semi-formal dance event: Navy sequin black velvet sweater dress c/o AMICLUBWEAR, and own Very Fine Dance Shoes Latin dance sandals


Black Tie, Military ball, formal ball/event

Semi-formal event

maxi dress as an example of what to wear for Valentine's day at a resort
Vacation resort: Unbranded maxi dress (own) necklace c/o Happiness Boutique


See these beautiful Valentine's day outfit inspirations. #valentinesday Click To Tweet


P.S.: You may be interested in reading what mistakes to avoid when dressing for Valentine’s Day.

P.P.S.: Are you still looking for Valentine’s Day gifts? Check out my gift guide for inspirations.



Top of the World Style linkup No. 293

banner of the weekly Top of the World Style linkup party on Thursdays

Welcome to the Top of the World Style linkup party.

Darlene from Aquamarina Style in olive pants, navy sweater
Darlene from Aquamarina Style became the Top of the World OOTD Readers’ Fav. Photo from her post


Carrie of A Stylish Fit in puffer bomber, T-shirt and camo pants
Carrie from A Stylish Fit became the Top of the World OOTD My Fav. Photo from her post


Christine of Bon Chic Style in a LBD, sandals, jewelry
Christine from Bon Chic Style became Top of the World Style Winner. Photo from her post


Congrats Ladies! Grab your award buttons.


Click here to enter


See these awesome looks at the Top of the World Style #linkup party. #timelessstyle Click To Tweet

I invite all fashion and style bloggers to co-host the top of the World Style linkup party. Just send me an email. What to throw your own party?

Do you want to get a free feature at the party? Then apply to become a co-host by sending me an email.

Photos: G. Kramm

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