11 Super-Chic Ways to Master Ladylike Dressing This Fall

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11 Super-Chic Ways to Master Ladylike Dressing This Fall

We first reported on this luxe new look last spring when polished ladylike jackets landed on the scene. And while the fitted jacket remains very much en-vogue, this season, it’s reimagined in a sleeker, more minimalist way. As of now, none is as beloved as Toteme’s collarless blazer, spotted on Vogue’s Executive Fashion Director, Lisa Aiken. Others like it include those from House of Dagmar to even & Other Stories. Styling-wise, complete the look in a preppy polo sweater, whether that’s Guest in Residence’s burgundy, sleeveless style or Miu Miu’s chartreuse choice, and an 1950s-inspired, A-line skirt from the likes of Tory Burch and Cos.

Then, there is the modern midi dress, which perfectly encapsulates our dressing mood for fall 2024: mature, stealth, and functional. With refined, flattering silhouettes and luxe materials leading the charge, options include Bottega Veneta’s two-toned wool dress, Altuzarra’s leather shirtdress, and Reformation’s corseted midi in a cool khaki color. Meanwhile, scarf-detail tops from Another Tomorrow and Khaite offer up a similar sophisticated vibe without the commitment of an all-in-one-outfit dress.

Lastly, no ladylike look is complete without an heirloom-in-the-making handbag. Coach’s top-handle tote is poised to be a fall hero buy, while styles from Staud, Savette, and Veronica Beard are just as luxurious. For more prim and proper accessories, find retro-inspired sneakers, kitten heel pumps, simple belts, and dainty jewels all for the modern woman. Below, 11 forever-chic ways to master ladylike dressing for fall.

Collarless Blazers

Our biggest style takeaway so far this fall? Collarless blazers are on everyone’s–and we mean everyone’s–wish list. Like the preppy lady jacket that dominated our spring shopping carts, the collarless blazer is a slightly sleeker version, complete with a clean-lined silhouette and rounded collar that shows a hint of clavicle. Toteme’s classic black choice is hard to beat, while cream, chocolate, and grey options from House of Dagmar, Loulou Studio, and Aligne pack a more playful punch. There’s even an under-$300 option from & Other Stories that offers up the same effortless polish without the price tag.

Toteme

wool-blend grain de poudre jacket

Another Tomorrow

belted padded satin jacket

House of Dagmar

collarless wool-blend blazer

Aligne

Daphne long-waisted blazer

& Other Stories

cropped collarless blazer

Modern Mididresses

No one can deny the eternal closet appeal of the shin-grazing, mididress. This fall, though, the style staple is getting a modernist, some would even say minimalist revamp. Draped delights from Bottega Veneta and Victoria Beckham dazzle from commute-to-cocktail, while Altuzarra’s leather shirtdress wins in both the sophisticated and practicality categories. Sleeveless styles from Reformation and Massimo Dutti are must-haves in any transitional capsule wardrobe; and same goes for Loulou Studio’s ribbed knit dress, which would look great with knee-high boots.

Altuzarra

Paulina belted leather midi dress

Victoria Beckham

Gathered wool-blend crepe midi dress

Loulou Studio

Hobas ribbed wool and cashmere-blend midi dress

Kitten-Heel Pumps

Give your ladylike look instant polish with a kitten heel. Prada’s two-toned block heels or Khaite’s crystal-embellished pair are perfect for the evening, while J.Crew’s animal-print sling-backs offer some welcome edge for day. T-strap styles from J.Crew and Neous are classic with a twist, playing well with everything from worn-in blue jeans to midiskirts.

Mango

slingback heeled shoes with buckle

Prada

brushed leather cut-out pumps

Khaite

Roosevelt crystal-embellished slingback pumps

Prim and Proper Midiskirts

Last season, we had Bottega Veneta to thank for bringing the 1950s-inspired midiskirt back into the picture. Fall’s slightly more updated versions include A-line midis from Prada and Cos to faux-leather finds from Tory Burch, J.Crew, and Toteme. Bonus points if you style yours with an aforementioned kitten heel or preppy polo shirt.

Cos

voluminous pleated cotton midiskirt

Bottega Veneta

paneled pleated wool-crepe midiskirt

Sophisticated Scarf Tops

Fashion’s favorite layering essential? A sophisticated scarf top. Sumptuous satin blouses from Another Tomorrow and Khaite look just as good tucked into a tailored trouser as they do peaking out underneath a workwear-approved blazer. Then, there’s Gucci’s sheer scarf top or Staud’s raisin-colored, sleeveless style–a.k.a. going-out tops to dazzle in ’til dawn. Scarf-detail sweaters from Cos and Róhe offer up a bit more coverage with no understated elegance lost.

Another Tomorrow

scarf-effect satin blouse

Staud

Canal merino wool turtleneck top

Gucci

tie-detailed silk-georgette blouse

Cos

scarf-detail wool turtleneck sweater

Heirloom-in-the-Making Top-Handles

Looking for a hero handbag to invest in this fall? One to pass down to your future children? Coach’s Empire carryall is a contemporary classic for a reason–capacious, expertly crafted, and already seen on the arm of many an industry insider this season. Others just as good include those from Khaite and Veronica Beard to Staud and Savette.

Coach

soft Empire carryall bag 40

Veronica Beard

large croc-embossed Dash bag

Savette

Symmetry Pochette glossed-leather tote

Staud

Harlow glossed-leather tote

Preppy and Polished Polos

No capsule wardrobe is complete without a roster of lightweight yet luxurious knitwear; a memo that rings just as true for the ladylike look. Preppy long-sleeved polos, like those from Le Kasha and Alex Mill are minimalist must-haves, while Miu Miu’s chartreuse choice and Loewe’s peplum pick are perfect for the fashion girl making her way down Madison Avenue.

Le Kasha

Fraga organic cashmere cardigan

Miu Miu

silk and cashmere cardigan

Guest in Residence

ribbed cashmere polo sweater

Loewe

mohair-wool blend polo sweater

Retro Sneakers

Fall fashion’s gone retro, with the spotlight on old-school style sneakers from Miu Miu, Dries Van Noten, and Adidas. And while a sporty sneaker may not immediately come to mind when thinking of ladylike dressing, these picks are as chic as they are versatile—and beloved by many a fashion darling.

Dries Van Noten

suede and leather sneakers

Mango

canvas sneakers with leather panels

Adidas

Japan suede-trimmed leather sneakers

Rag & Bone

retro mixed leather runner sneakers

Peacoat Perfection

According to the fall/winter 2024 runways and ladylike dressers from far and wide, a peacoat is the ultimate outfit topper. Saint Laurent’s navy take is pure perfection; the same can be said of Chloé’s always-a-good-idea camel coat. Options from the high-street mimic the mastery, with all eyes (and shopping carts!) on J.Crew’s speckled, relaxed-fit peacoat.

Saint Laurent

oversized double-breasted wool-twill coat

Mango

double-breasted virgin wool coat

Cos

double-faced wool peacoat

Proenza Schouler

Rowen double-breasted wool-blend felt coat

J.Crew

relaxed double-breasted blazer

Elegant Belts

An understated yet elegant leather belt is key to pull a look together. Go modern with Toteme’s skinny, croc-embellished belt, Khaite’s python-effect pick, Saint Laurent’s burgundy beauty, or Frame’s chain-link choice. For something true to the classics, options from H&M and Anderson’s won’t disappoint.

Toteme

embellished croc-effect leather belt

Finishing Touches

Dainty jewels, like a pair of Dorsey drop earrings or Ragbag’s pearl necklace, are sure to sparkle all season long. And for the ultimate sign of luxury, opt for Cartier’s timeless leather watch or David Yurman’s mixed-metal chain bracelet. Did someone say arm candy?

Ragbag

Odette pearl collar necklace

Lié Studio

The Diana gold-plated hoop earrings

Dorsey

Sabine lab-grown drop earrings

Cartier

Baignoire mini 18-karat gold and glossed-leather watch

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