Already have an account?
Get back to the

Valentine’s Day Clothes for Older Women

Fall in love with our Valentine's Day fashion picks!


Woman's World has affiliate partnerships. We receive compensation when you click on a link and make a purchase. Learn more!

Looking for the perfect Valentine’s Day clothes? Whether you’ve always gone all out getting dressed up for the love holiday or are looking for outfits for a special occasion, we know finding the right fits can be challenging, especially for women over 50.

Women’s World has curated some of the best Valentine’s Day styles for older women, from kitten heels to versatile denim jeans, dresses, and even pajamas. Create your look with our hand-picked ideas below!

Lisa Red Kitten Heels with Pearl T Straps and Bows

Red Kitten Heels for Older Women

Buy from Bella Belle Shoes, $365

These kitten heels provide just enough height and come with enough padding to keep you comfortable no matter how long you’re wearing them! Perfect for a Valentine’s Day date any time of day, these kitten heels can be dressed up or down depending on your personal style.

Kitten Heel Specs

  • Heel Height: 2.5 inches
  • Upper Material: Silk
  • Lining Material: Leather lining

Trina Turk Sweetheart Sweater

Pink & Red Heart Sweater for Older women

Buy from Trina Turk, $288

This classic crewneck sweater features a red and pink knitted heart design that’s perfect for the Valentine’s Day season. Crafted with soft, breathable Merino Wool, this long-sleeved heart sweater pairs perfectly with your favorite denim or patterned trousers!

Sweater Specs

  • 100% Merino Wool
  • Ribbed cuffs and hem
  • Runs true to size

Bisou Cross Halter Bodysuit

REd Bodysuit for Older Women

Buy from Cosabella, $125

Elevate your wardrobe with this bodysuit from the Bisou Collection – a look designed to be seen. The line is a fusion of innerwear and outerwear that effortlessly transitions from day to night that are designed to empower you while providing comfort and confidence.

Bodysuit Specs

  • Luxuriously micromodal and cotton blend
  • Non-padded, revealing open front
  • Full coverage rear with snap closure
  • Cotton lined gusset

SKIMS Soft Lounge Long Sleeve Dress

Red Floor-Length Dress for Older Women

Buy from Nordstrom, starting at $62

A classic everyday style, this square-neck maxi dress in ribbed stretch modal from Kim Kardashian’s SKIMS collection. Pictured here in Brick, this dress will hug your body in all the right places!

SKIMS Dress Specs

  • 91% modal, 9% spandex
  • Slips on over head
  • Square neck

NYDJ Relaxed Slender Jeans

Jeans for Older Women

Buy from Nordstrom, $119

Loose through the thigh and straight from knee to hem, these stretchy jeans flatter with Lift Tuck® Technology! They’ll pair well with everything from blouses to bodysuits and beyond this Valentine’s Day.

Jean Specs

  • 30″ inseam; 15″ leg opening; 10″ front rise; 15″ back rise (size 8)
  • 67% cotton, 26% polyester, 5% viscose, 2% elastane

Quince 100% Washable Silk Skirt

Silk Skirt for Older Women

Buy from Quince, $60

This washable silk skirt (!!) will pair perfectly with just about every top you own. It’s super stylish with a bias cut. Plus, the silk fibers contain amino acids that make it amazing for skin nourishment, hypo-allergenic, and naturally thermoregulating to help maintain body temperature! Get it in Salsa or Burgundy (pictured) for the perfect Valentine’s Day outfit.


  • Crafted from washable, 100% mulberry silk in a satin finish
  • 19mm fabric weight for a premium drape and hand-feel
  • Hidden elastic waistband for an easy, comfortable fit

Ann Taylor Metal Heart Bracelet

Heart Bracelet for Older Women

Buy from Ann Taylor, $60

This goldtone heart bracelet is the perfect accessory to any Valentine’s Day look whether you’re going casual or dressy.

Bracelet Specs

  • 6 1/2″ length
  • 1″ extender

Kate Spade Heart Hardware Micro Flap Crossbody

Heart-Themed Purse for Older Women

Buy from Kate Spade, $140

This Valentine’s Day, hit the town with your important things and leave all the bulk behind with this Kate Spade crossbody bag. The heart detail closure makes it the perfect V-Day accessory!

Crossbody Purse Specs

  • 1.97″ W x 4.88″ H x 5.12″ D
  • Strap Drop: 22″
  • Zip closure

Adore Me Sammi Heart Purple PJ Set

Valentine's Day PJs for Older Women

Buy from Adore Me, $22

This heart pajama set is made from 100% recycled satin for a luxurious and soft feel and includes a long-sleeved button-down and matching shorts. The snarky Spank Me print features candy hearts that say things like: ‘spank me,’ ‘cute butt,’ ‘bite me,’ and ‘talk dirty’ — a fun, flirty sleep set perfect for V-Day!


  • 100% Recycled Polyester Satin
  • Collared long sleeve button down
  • Matching short

Want more Valentine’s Day inspiration? Keep reading!

Valentine’s Day Gift Ideas for Everyone in Your Life From Partners to Coworkers and More

5 Free Printable Valentine’s Day Cards That Aren’t Cliché or Boring

12 Valentine’s Day Gifts Your Husband Will Actually Want

Use left and right arrow keys to navigate between menu items. Use right arrow key to move into submenus. Use escape to exit the menu. Use up and down arrow keys to explore. Use left arrow key to move back to the parent list.