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Learn the Art of Modern Ladylike Dressing

Duchess Catherine, Grace Kelly—channel the style icons of many generations with these tips.

Let’s be honest, we all have a pin or two (. . . or 300) of Kate Middleton on Pinterest. The modern-day royal has revived the art of ladylike dressing. Along with the Duchess, classic and feminine style icons such as Jackie Kennedy, Grace Kelly, and Audrey Hepburn prove that the term ladylike doesn’t have to mean frumpy, uptight, or dated. No matter what trends are dominating the runways or magazines, classically feminine style remains timeless.

The same feminine elements that make Kate’s outfits as well as the outfits of starlets of the fifties and sixties so classic are easy to replicate. By incorporating just a few ladylike elements, you too can exude elegance.

The Basics

modern ladylike style fashion classic feminine dressing outfit inspiration Kate Middleton

Photo Credit: Kelly West

To bring out your classy, conservative side, start with a few basic silhouettes. They serve as a great starting point from which to pick your clothes.

1. Half sleeves: Half or three-quarter-length sleeves have an elegant vintage vibe. Although Audrey Hepburn may be most remembered in a sleeveless black dress (you know the one), she was often seen in longer sleeves—even turtlenecks. Opting for more arm coverage is flattering for the figure, as it highlights the elegant lines of your arms.

2. Well-fitted: Settling for an ill-fitted dress is never a good investment. Find a tailor near you, and experiment with different styles until you know what shapes work best for your body type. You don’t have to go as far as sewing weights into your hem to prevent windy-day wardrobe malfunctions, as the royals allegedly do, but when your wardrobe is full of tailored dresses that look like they were made for you, you will feel more comfortable and confident in your outfit choices.

3. Knee-length or just above the knees: A dress or skirt that skims the knees or goes a couple inches above is universally flattering and really emphasizes your feminine silhouette, highlighting the graceful lines of your legs. Pencil skirts especially highlight your curves in a modest and modern way. The late Princess Diana often wore this silhouette. The key is to find a pencil skirt that fits you perfectly and is made from quality material; you want to avoid the too-tight, see-every-bump spandex look.

4. Heels and ballet flats: Sleek ballet flats or heels dress up any outfit with a delicately feminine touch. If you love Audrey Hepburn’s style, invest in a pair of black ballet flats pronto! To modernize this classic staple, try a bold color or print; you can often find me in a pair of bright red heels or flats with a quirky print.

Go Fancy at Night

modern ladylike style fashion classic feminine dressing outfit inspiration Kate Middleton

Photo Credit: Phillip Van Nostrand

When dressing for a special event or a party, you don’t have to expose a lot of skin to make a statement. I opt for making my outfit memorable in a different way—such as intricate lace detailing, an embellished belt, or a great color or print. Adding a little whimsy to your look, such as a flouncy tulle skirt, lends a playful and flirty element without being over-the-top. Classic style icons are known for dressing with modesty but still showing their personality. I find that the key to feminine and ladylike dressing is in the refined subtleties; embellishments, lush fabrics, or beautiful prints will make an impact without being excessive.

  1. Sparkle details: embellishment or oversize jewelry
  2. Bold color or print: stripes or pastels
  3. Statement shoes: metallics or print
  4. Fancy fabric: lace or tulle detailing

Business Professional

Photo Credit: Phillip Van Nostrand

Photo Credit: Phillip Van Nostrand

Most of us have a business casual office policy, which is the perfect setting for a more refined style. The easy option is to go for a pencil skirt—it’s an easy way to make a casual look a bit more feminine, especially if you find one in a floral print or a funky color. I often will pair a pencil skirt with an eyelet lace top and pointy heels or flats. This way, I’m comfortably casual and can take this look from my day job to running errands.

  1. Fun fabric: eyelet lace
  2. Classic accessories: leather purse or statement jewelry
  3. Updated pencil skirt: floral print or funky colors
  4. Statement shoes: pointy toe or bold color

Casual Day Off

modern ladylike style fashion classic feminine dressing outfit inspiration Kate Middleton

Photo Credit: Brittanny Taylor

For an even more casual look, I often wear a denim-on-denim look—a pencil skirt with a masculine chambray button-up. Sounds pretty casual, right? But when I add feminine details to the denim skirt, such as jeweled embellishments, this adds some sparkle without being over-the-top. Bold red flats really brighten up the outfit and go perfectly with an equally bold red lip. The overall look is one that’s streamlined and still simple.

  1. Feminine details: embellishments
  2. Casual fabric: denim
  3. Bold color: red shoes
  4. Feminine makeup: red lip
Photo Credit: Kelly West

Photo Credit: Kelly West

If dressing this way is completely foreign to you, but it’s something you want to try, remember that ladylike style doesn’t necessarily mean you have to embrace Kate’s fascinator hats or matching setsfeminine elements can be as bold or as subtle as you choose. Whether it’s swapping an elegant slingback heel for a cooler strappy statement heel or forgoing pants for a fitted pencil skirt, you can add small doses of femininity in ways that feel right for you. I believe in dressing in a way that reflects who you are so that you feel comfortable and confident. There’s nothing more ladylike than that!