Valentine’s Day is the perfect excuse to show off your personal style, whether you’re going out for a romantic dinner, enjoying a fun night with friends, or just indulging in some self-love. But if you’re over 50, finding the right balance between trendy and age-appropriate can feel tricky. You want to look fabulous, but you don’t want to feel like you’re trying too hard or stuck in a fashion rut. So, what should you wear this Valentine’s Day, and what should you avoid? We’ve got the ultimate guide to help you navigate the season of love in style!
What to Wear: Chic, Sophisticated, and Playful Looks
Bold Red or Pink
Single Button Twill Blazer | White Button-Up | Flare Leg Twill Pants | Pink Strappy Sandal Heels
When it comes to Valentine’s Day, these colors are iconic for a reason. But if you’re over 50, it’s all about choosing shades that complement your skin tone. Think deep reds, berry tones, and soft pinks. A red dress or a pink blouse paired with a sleek skirt or tailored pants will give you a fresh, vibrant look. Try adding a pop of red lipstick for an extra touch of glam!
Flattering Silhouettes
Similar Sweater Dress | Longline Blazer | Pink Strappy Block Heels | Layered Coin Necklace | Large Gold Hoop Earrings
Gone are the days of squeezing into body-con dresses just to feel “on trend” _ – especially for Valentine’s Day. Choose styles that highlight your best features while offering comfort. A well-fitted A-line dress or a classic wrap dress can show off your curves without feeling overly tight. A midi skirt with a flowy blouse is another fabulous combo that offers elegance and movement.
Statement Accessories
Similar Multi-Strand Pearl Necklace | Lightweight Cashmere Crewneck Sweater | Mid-Rise Straight Ankle Jeans | Pearl Stud Earrings
Accessorizing is the key to elevating any outfit, especially on a special occasion like Valentine’s Day. Consider adding statement jewelry—think chunky necklaces, oversized earrings, or a bold bracelet. A sophisticated scarf or a metallic clutch can also take your look to the next level without being over the top.
Comfortable, Chic Footwear
Tweed Skirt | Pink Turtleneck | Denim Jacket | Metallic Handbag | Similar Pink Flats | Caviar Earrings | Caviar Bangle | Caviar Watchband
High heels can be painful, but that doesn’t mean you have to sacrifice style on Valentine’s Day. Opt for a classic pair of ballet flats or low-heeled pumps. Block heels are also a great option if you want the height without the discomfort. A pair of stylish boots can be a great choice if you’re planning a more casual Valentine’s celebration, pairing beautifully with dresses or trousers.
What to Avoid: Fashion Faux Pas After 50
Too Much Skin Exposure
While showing off a little skin can be sexy, it’s essential to avoid going overboard on Valentine’s Day. Think twice about ultra-short skirts or low-cut tops. Instead, focus on showing off one feature at a time—whether it’s your arms, legs, or neckline. A dress with a tasteful neckline, or a sleeveless top paired with a tailored jacket, strikes the right balance between flirty and sophisticated.
DO WEAR: Rib Boatneck Tee | Red Skirt | Similar Suede Pumps | Patent Leather Belt
Overly Trendy Items
It’s fun to try out the latest trends, but after 50, it’s important to choose what works for you. Wearing something because it’s trendy—like a cropped top or overly distressed denim—can sometimes feel more forced than fabulous. Stick with classic, timeless pieces that flatter your body shape this Valentine’s Day. A chic tailored blazer or a sleek monochrome outfit can never go out of style.
DO WEAR: Similar Pink Blazer | Similar Pink Trousers | Alternative Pink Sweater Shell | Similar Pink Pumps
Clothes That Are Too Baggy
While oversized clothes are on trend, they don’t always flatter every body shape. Avoid drowning in fabrics that hide your shape completely. A loose top can be beautiful when paired with slim-fit trousers, or a flowy skirt can look fantastic with a fitted top. The goal is to look relaxed yet polished—baggy clothing can often do the opposite, making you appear shapeless.
DO WEAR: Ann Taylor Cashmere V-Neck Sweater | Ann Taylor Sophia Pant | Dolce Vita Largo Flats
Excessive Sequins and Glitter
A touch of sparkle is great for a festive occasion, but when in doubt, less is more. Keep the sequins to a minimum and focus on luxe fabrics like satin, velvet, or silk that naturally have a shine. A shimmery bag or a metallic accessory can elevate your look without making you feel like you’re wearing a disco ball on Valentine’s Day.
DO WEAR: Washable Silk Tie Neck Blouse | Similar Faux Leather Pant | Hazel Pointed Toe Pump | Similar Mirror Silver Bag | Alternate Mirror Silver Handbag
Closing Thoughts
Valentine’s Day is about celebrating love, and the best way to do that is by feeling confident and comfortable in your outfit. Choose pieces that reflect your personality, whether that’s a bold red dress, a sleek suit, or a cozy chic sweater. After 50, fashion is all about embracing your age and rocking it with style, so don’t be afraid to experiment while still staying true to your personal taste. With the right choices, you’ll look and feel fabulous this Valentine’s Day—and beyond! Valentine’s Day is the perfect time to have fun with your wardrobe. So, are you ready to strut your stuff? What style will you be wearing this year? Share your Valentine’s Day fashion plans in the comments!
About The Author
Like I mentioned before, I love pink!
Me too, Sherry!
Nice options, Beth!
My Valentine’s outfit: A vintage red wool blazer (made in Hong Kong!) with bracelet-length sleeves in red silk trim, ever-so-slightly distressed jeans with embroidered flowers (red, pink, green) on one leg and either a pink or red crew-neck t-shirt under the blazer. Ugg black suede clogs (wood bottoms). Going to dinner at a nice Italian restaurant with my husband and best lifelong friend/husband from MI, who are stopping in NC on their way to FL to catch a Caribbean cruise.
Happy Valentine’s Day, Carolina Girl. Your outfit sounds perfect! Enjoy date night!
I LOVE the all pink outfit! What a statement!
And I appreciate the thoughtful tips regarding tasteful dressing after age 50. Wish I’d known sooner about wearing a fitted top with fuller pants or an oversized top with fitted bottoms. It really does make a difference.