Modern Women's Fashion with Classic Ladylike Style

Yelena Johnson
Woman wearing white skirt and blue blouse

Building a Classic Wardrobe With a Modern Slant

Classic, ladylike clothing is one trend that will always be in style. When building a modern version of the classic wardrobe, get inspired by style icons like Grace Kelly and Audrey Hepburn. Many of the clothes they wore in their heyday can still be found on today's catwalks. By building a few of the classic pieces into your wardrobe, you gain a greater versatility as well as pieces that will never fade. Even better, you can mix and match the latest styles with all the following classics to create modern takes on a tried and true ladylike look.

Seen here, a classic button-down and a ladylike skirt offer timeless style that gets a modern touch with a statement necklace.

To learn more about the items in this gallery, click on the "More Details" link above each image.

Tuxedo ruffle top in polkadot silk
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Tuxedo Ruffle Top

This chic and stylish button down shirt (about $130 from J. Crew) is a seriously versatile addition to a lady's wardrobe. The soft shape and the ruffles give this top a decidedly feminine feel, and its classic shape allows it to be paired with skirts as well as pants. Thanks to the small-scale polka dot pattern it can be dressed up or down.

Ways To Wear It

  • Casual: Pair it with tailored jeans, a belt and leather ballet flats.
  • Work: Add a jacket over the top of the blouse and don a pair of work slacks with heels for a polished look.
  • Dressy: Roll up the sleeves, pop the collar, and pair with a chunky necklace and a-line skirt in a formal fabric.
Button-front skirt in double-serge wool
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Button-Front Wool Skirt

Not only is wool one of the all-time classic fabrics, but the silhouette of this button-front skirt from J. Crew (under $100) has undeniably stood the test of time as well. A knee-length skirt is very versatile -- it pairs beautifully with an array of different tops. The wool fabric is best worn from fall through winter, although chilly spring climates call for a nice wool skirt as well.

Ways to Wear It

  • Casual: Dress this ladylike skirt down with a tucked-in v-neck tee or a simple white polo with a ladylike peter pan collar.
  • Work: A silk crew neck shirt with flouncy sleeves, cute comfy heels and this skirt paired together is a great look for the office.
  • Dressy: Sky-high heels, a silky top and layers of pearls make a dressy outfit that is perfect for an evening on the town.
Eliza J Dot Mesh Bodice Fit & Flare Dress
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Dot Mesh Bodice Fit and Flare Dress

A fit and flare skirt and boatneck three-quarter length top make this dress (approximately $160 from Macy's) a consummate classic. Though the polka dots are a classic pattern, the large-scale print and mesh effect modernizes the dress.

Ways to Wear It

  • For fall and winter, add tights in a maroon or olive hue, black pointy-toed heels, and a cropped tuxedo jacket.
  • For spring, pair the dress with ladylike ballet flats or smoking slippers in a pastel hue and cardigan for warmth.
  • In summer, don a lightweight jean jacket on chilly nights and slip into a pair of peep-toe sandals to finish the look.
Dress the Population Maya Lace Fit & Flare Dress
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Formal Lace Dress

For formal events, choose a dress with a classic cut in neutrals. This Maya fit and flare dress is a vision thanks to the duality of the nude base and black patterned overlay. It's a beautifully modern take on classic shapes and colors that make it a go-to pick for dressy events. At just under $250 it's a bit of an investment, but a classic little black dress can last for a decade in your wardrobe.

Ways to Wear It

  • For very formal events, a classic fur stole or cropped jacket is a great way to keep this dress warm on a chilly evening.
  • Dress it down with a crew-neck cashmere sweater over the top, and add tights and boots to finish the look.
  • Layer a lace bolero over the top of this dress to cover up a bit of skin, or modernize it by donning a bohemian sheepskin jacket like a rockstar.
JS Collections Soutache Lace Midi Dress
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Modern Sheath Dress

For a bold modern take on the classic sheath dress, consider this pretty option from JS Collections for $350. A beautiful lace dress is modernized by the oversize geometric patterns and combination of blue and white hues.

Places to Wear It

  • Baby showers, bridal showers and luncheons are begging for this dress to grace them with its statement-making presence.
  • Date night is another perfect occasion to rock this one-of-a-kind number thanks to its demure, ladylike length and bold attention-getting pattern.
  • Cocktail parties are a great opportunity to show off your style. Even better, the pattern makes such a statement that no accessories are required -- getting dressed has never been easier.
Theia High-Low Ball Gown
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Velvet and Jacquard Ballgown

This velvet and jacquard ballgown by Theia (just under $1000) is the epitome of a modern classic. While silk and velvet fabrics are two very old-world textiles, the modern shape of the dress (complete with pockets) make it perfect for the forward-thinking, trendsetting woman.

Places to Wear It

  • Galas and Formal Fundraisers: You'll be the belle of the ball when you enter the room donning this stunner.
  • Black Tie Weddings: Just be careful not to upstage the bride.
  • Ballet or the Opera: Go all out for the opera in this unforgettable dress. You just may get your own standing ovation.
Eliza J Embellished Floral Jacquard Fit & Flare Gown
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Floor Length Embellished Floral Dress

Channel Grace Kelly in this floor-length classic dress by Eliza J. (approximately $280). As with the previous gown, this one features a traditional jacquard fabric. Though the cut is also more classic, the pearl-embellished neckline sets it apart and makes it a great pick for upcoming formal events. Thanks to the pearls around the neckline, you also won't have to worry about accessorizing -- simply pop on a pair of heels that will keep you comfortable all night beneath the sweeping skirt.

Eliza J Jersey & Metallic Faille Ballgown
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Ladylike Modern Ballgown

The classic ballgown skirt of this stunning dress (about $240 from Nordstrom) is modernized with the simple black three-quarter length top. The oversized bow and large-scale floral pattern are also contemporary takes on classic looks, bringing the look of this into the present day.

Though this dress is certainly formal, there are ways to dress it up or down via accessories and hairstyling. Wear your hair down with loose waves to embrace a less dressy air. Or, go ultra formal by adding bejeweled bangles, a pair of large sparkly earrings and a high-swept chignon.

Coach Lara Flat
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Floral Flats

These gorgeous floral Coach ballet flats (about $175 at Bloomingdale's) are the perfect complement to a ladylike wardrobe. A comfortable pair of flats are a total workhorse -- they go just as well with jeans as they do with a skirt or dress.

Ways to Wear Them

  • Ballet flats look lovely with a-line knee-length skirt and a button-down top like the ruffled tuxedo blouse.
  • Modernize the flats by wearing a simple t-shirt tucked into ripped boyfriend jeans with rolled cuffs. It's a look that exudes effortless-casual chic.
  • A sheath dress would also pair nicely with these floral ballet flats -- add a jacket or cardigan for an extra layer of interest and warmth.
Michael Kors Sabrina Ballet Flats
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Sleek Ballet Flats

While traditional ballet flats have an aura of sweetness (thanks in large part to the soft rounded toe and traditional bow), these Michale Kors ballet flats (about $125 at Bloomingdale's) take no prisoners with their sleek and assertive shape. They offer a serious, more modern take on the stereotypical ballet flat style, and help dress up whatever you are wearing on top.

Ways to Wear Them

  • These stylish beauties are the perfect pick for a long day at the office. They go great with work slacks and skirts alike, and have the formality of a high heel without the discomfort of the height
  • Pair these pretty flats with a modern leather sheath dress for a look that screams New York-chic.
  • A button-down top, fitted black jeans with frayed knees and these flats is a casual yet pulled-together outfit that can go almost anywhere.
 Ivanka Trump Carra Houndstooth Pointed Toe Pumps
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Houndstooth Pointed-Toe Pumps

Houndstooth is one of those classic patterns that has stood the test of time. What makes these Ivanka Trump heels (available at Bloomgindale's for about $140) so fun is that typically houndstooth is on clothing, not footwear. If the sheer wearability and the classic nature of these isn't enough reason to add them to your wardrobe, the heels are also a great value at under $150.

Ways to Wear Them

  • Tapered pants and heels are a leg-lengthening combination that flatters almost every figure.
  • An all-black outfit looks great with a pop of patterned heels, and this houndstooth pair is no exception.
  • For fall, try wearing these pumps with blue jeans and a cozy black sweater.
Ralph Lauren Tate Dome Satchel
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Sophisticated Dome Satchel

Ralph Lauren is known for their mastery of the classic ladylike look, including their accessories. This dome satchel (under $200 at Macy's) is oozing sophistication, yet still makes a modern statement with its bold red hue. Keep this purse as a background player in your outfit by wearing it with other rich fall and winter colors, or let it stand out and make its mark by contrasting it with black and white clothing.

Michael Kors Selma Medium Satchel
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Classic Satchel in a Modern Color

The classic satchel shape gets a modern update with a pop of blush pink. What works well with this handbag (just under $300 at Macy's) is that the simple shape paired with the feminine color creates a nice balance; it's not too girly, and not too business-like. Thanks to this, along with the handles that can be worn over the arm as well as across the shoulder(s), make this satchel an easy favorite.

Vera Bradley Quilted Tess Crossbody
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Quilted Handbag

A quilted satchel is one of those eternal handbag classics. The shape, color, and quilting in this Vera Bradley bag (about $200) are all classic. This purse can be worn daytime to nighttime with almost anything, and deserves a prominent place in any lady's handbag collection.

Maddie pant in bi-stretch wool
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High-Waisted Wool Slacks

Not only are these J. Crew pants a flattering cut and a classic color, but they also contain the holy grail of womenswear: two-way stretch. The usual reservations about purchasing wool pants (i.e. an uncomfortable fit) are thrown to the wind thanks to the Lycra blend from which these pants are constructed. The medium-high waist is another reason these pants are perfection - they are high enough to eliminate concerns about love handles without being so high that you feel constricted.

Ways to Wear Them

  • Dress these down with a pair of nicer sneakers (no socks) and a sweater for casual Fridays.
  • Up the polish of your look by donning a pair of ladylike heels and roll up the sleeves of a button-down shirt.
  • Go modern with a leather sleeveless crewneck top and black ankle booties.
Regent topcoat in double-serge wool
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Stylish Topcoat

Few coats are more classic than a wool topcoat, especially when that coat is in a beautiful camel color like this one from J. Crew (about $350). Describing what this coat looks good with is nearly impossible because the options are truly endless. A topcoat looks great worn open over a tee, jeans and Keds sneakers, but can be thrown over a ballgown as well without looking out of place. Of all the classic, ladylike items to have in one's closet, this ranks among the best of them.

Perfect-fit mixed-tape cardigan sweater
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Ladylike Long Cardigan

A long cardigan, like this J. Crew style for about $50, is a classic ladylike piece that has stayed relevant since the 1920s. It's extremely versatile, flattering and can be worn with so many different types of outfits that it has claimed its place in women's wardrobes across the Western world as a fall and winter essential.

Ways to Wear It

  • Layer a long cardigan over a tank top and jeans for a pulled-together casual look.
  • Sheath dresses look great with a long cardigan over the top; leave it open for extra movement and flow.
  • On cooler days, a cardigan makes a lovely addition to a button-down shirt. It's a perfect pick for days when you need to look polished.

Even if you prefer trendy styles, adding a few pieces that have an updated classic look and ladylike sophistication can help you expand your wardrobe with versatile, polished clothing for every occasion.

Yelena Johnson
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Modern Women's Fashion with Classic Ladylike Style