80+ Pieces of Transitional Clothing to Tackle the In-Between Season in Style

Nili Lotan

Kedem leather-trimmed suede jacket

$2995

MODA OPERANDI

The Row

Hubert cotton wide-leg pants

$1350

H&M

suede driving shoes

$90

H&M

Banana Republic

Sabbia oversized Italian trench coat

$350

Proenza Schouler

Moore glossy leather midi skirt

$2990

Khaite

Roosevelt crystal-embellished slingback pumps

$1380

KHAITE

Staud

Siren scarf-detail sweater

$450

‎

Fashion’s Gone Out West!

Just in time for apple-picking season, plaid shirts (and more Western wear) have officially gotten the high-fashion seal of approval, from the street style scene to the runways as seen at labels like Bottega Veneta, Toteme, Róhe, and more. Styling-wise, sport your flannels with a sleek black jean, pair of pointed-toe mules, and a day-to-night clutch for a playful vibe shift that channels the best of summer and fall.

Róhe

Checked cotton-flannel shirt

$350

Re/Done

studded high-rise flared jeans

$395

The Row

Mel leather clutch

$1450

Bottega Veneta

Lewis block-heel pumps

$1450

Toteme

wool-blend grain de poudre jacket

$1040

Madewell

x Alexa Chung mini skirt

$298

Loewe

Campo leather knee boots

$2300

Reformation

Clara cashmere cardigan

$198

‎

The More Modern the Midi, the Better

No one can deny the eternal closet appeal of the LBD. This fall, though, the style staple is getting a modernist, some would even say minimalist revamp. Take this model-off-duty, for example. On the cobblestone streets of NYFW, she slipped into Proenza Schouler’s cowl-neck, belted version. A pair of lug-sole boots toughens up the look, while the latest It bag keeps it right on trend. Layer in an oversized khaki trench coat on days when the weather dips below a tepid 60 degrees.

Proenza Schouler

Yoko midi-dress

$1290

Banana Republic

Italian leather boots

The Frankie Shop

Mavis twill trench coat

$345

Chloé

studded leather shoulder bag

$4600

Victoria Beckham

hooded leather-trimmed wool coat

$2590

J.Crew

wide-leg corduroy trousers

$148

J.CREW

&Daughter

argyle wool cardigan

$580

Coach

soft Empire carryall bag 40

$695

COACH

‎

How to Master Fashion-Forward Layering

Transitional weather is notoriously hard to navigate. One day you can expect warm, humid temperatures that rival mid-summer and the next, there’ll be a breezy, chill in the air that calls for your coziest sweater or lightweight jacket. Here, follow this street styler’s suit and drape a boxy, camel-colored blazer over your shoulders (or arm!) just in case—you can never be too prepared, after all. Otherwise, the look includes a striped button-up shirt, pair of straight-leg style blue jeans, and a chunky suede loafer to ground the look with fall elements.

Derek Lam 10 Crosby

Wesley striped shirt

$325

REFORMATION

Val 90s straight-leg jeans

$168

Gucci

horsebit ankle boot

$1270

GUCCI

Banana Republic

Siena slim wool blazer

Toteme

embroidered scarf jacket

$1130

Massimo Dutti

suede leather midi skirt

$449

MASSIMO DUTTI

Khaite

Cate bag

$4800

KHAITE

Simkhai

Burke draped jersey midi dress

$595

MODA OPERANDI

‎

Keep it in the Color Family

Splashy hues aren’t necessarily synonymous with the minimalist movement, however, this industry insider proves it can be. Sport a light pink button-up with a classic pair of blue denim and to add some welcome coverage, drape a chunky, mauve-colored crewneck over your shoulders. A pair of pointed-toe black wedges keeps things feeling sophisticated.

Loewe

belted shirt

$1850

LOEWE

Veronica Beard

Taylor double-seam jeans

$378

VERONICA BEARD

Staud

Aura ribbed wool-blend sweater

$325

Toteme

Wedge suede slingback pumps

$660

Alex Mill

Chiltern Street jacket

$325

ALEX MILL

Aje

Resonance denim midi skirt

$425

Altuzarra

Grady argyle cable-knit wool turtleneck sweater

$895

Banana Republic

studded leather belt

$140

‎

Not Your Everyday Leather Jackets

It’s jacket season! And what better way to celebrate than with an oversized moto jacket or a cropped leather version? Vogue’s executive fashion director, Lisa Aiken, took to the fashion week streets in the elevated essential, which she layered over a ribbed tank dress and pair of sporty Adidas sneakers. On the other side of the sartorial spectrum, Vogue’s senior fashion market editor, Madeline Fass, wore hers with a sheer midiskirt, gray cashmere crewneck, and a pair of ’90s-inspired heeled thong sandals. Shop Aiken’s look, below.

Mango

leather crop blazer

$400

MANGO

Róhe

ribbed cotton-blend bouclé maxi dress

$460

Adidas

Samba LT leather sneakers

$100

Alaïa

Le Teckel textured-leather shoulder bag

$2490

Frame

wool-blend cardigan

$480

The Row

Fleur pleated midiskirt

$1750

Madewell

April ballet flats

$110

J.Crew

long barn jacket

$398

J.CREW

‎

Mix-and-Match: The Textures Edition

Textures of all kinds thrive during the fall months, from corduroy and suede to fringe and even sequins! Vogue’s fashion market and collaborations director, Willow Lindley, combined two of our favorites for a look that’s a masterclass in contrast. Steal her style, below, starting with Madewell x Alexa Chung’s suede blazer, Loewe’s khaki green corduroys, and to polish it all off, a plain, but perfect white tank and pair of studded ballet flats from Tory Burch.

Madewell

x Alexa Chung double-breasted blazer

$498

Loewe

corduroy trousers

$990

The Row

Misty ribbed cotton-jersey tank

$670

Tory Burch

studded ballet

$498

TORY BURCH

Róhe

Scarf-detailed sweater

$600

Cos

paneled leather racer midi skirt

$450

Toteme

belted croco-embossed bucket bag

$1340

24S

Bottega Veneta

double-breasted shearling coat

$8900

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For Reliable Style Support, This Timeless Layer Always Delivers

The foundation of any transitional outfit is none other than a trench coat. Beloved for its versatility and lightweight coverage, Saint Laurent’s classic khaki style is a prized pick. Styling-wise, slip it on with Anine Bing’s cashmere tee, Tory Burch’s asymmetrical denim skirt, and a pair of leopard-print pumps.

Saint Laurent

oversized belted cotton-twill trench coat

$4650

Source Unknown

Nalita slingback pumps

$275

SOURCE UNKNOWN

ANINE BING

Jackson cashmere sweater

$400

Tory Burch

deconstructed denim skirt

$368

TORY BURCH

Róhe

lace slip dress

$670

RÓHE

Vince

leather bomber jacket

$1395

Dries Van Noten

leather sneakers

$475

The Row

Half Moon bag

$1520

FWRD

Uniqlo

striped cotton shirt

$40

UNIQLO

Toteme

pony hair skirt

$3000

TOTEME

AGOLDE

Jay cotton-jersey T-shirt

$100

Frye

Harness boots

$598

FRYE

Khaite

Lina shoulder bag

$1480

Khaite

Arden sandals

$1080

JW Anderson

tie-detailed knitted sweater

$790

Helmut Lang

Carpenter jeans

$445

shopbop

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Invest in New Knits

The new knits on the scene this season aren’t your everyday crewnecks and cardigans. Some of the small, but mighty details to note include tie-front details silhouettes, scarf-like tops, dramatic buttons, and new takes on cashmere tanks. Here, style yours with a dark-wash jean, strappy heeled sandal in a bold red hue, and a python-effect handbag.

Dries Van Noten

belted turtleneck midi dress

$1595

Staud

Wally flat boots

$495

Uniqlo

trench coat

$130

UNIQLO

Róhe

draped-sleeve armhole sweater

$530

Mango

check parka with contrasting collar

$200

MANGO

Max Mara

Gilly wide-leg corduroy trousers

$795

NEIMAN MARCUS

Staud

Canal top

$295

FWRD

Tory Burch

studded ballet flats

$498

TORY BURCH

The Frankie Shop

Lui oversized cotton shirt

$110

Proenza Schouler White Label

Rosalyn pleated skirt

$525

Staud

Cami boots

$550

Nili Lotan

Edmont double-breasted wool coat

$2095

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Striped Rugby Shirts Bring the Cool

Preppy, striped polos were a mainstay on the spring/summer 2024 runways with picks from Miu Miu, Dries Van Noten, and Loewe taking up prime real estate in our wardrobes. For fall, keep things sleek and simple by teaming up the menswear-inspired It item with a longline denim short, kitten heel, and minimalist handbag.

J.Crew

relaxed rugby T-shirt

$90

J.CREW

Agolde

Nolan shorts

$200

Toteme

Toteme leather thong sandals

$450

Toteme

belted naplack-leather bucket bag

$1340

TOTEME

Allude

cashmere sweater

$580

Ganni

twill suiting trousers

$295

Joseph

Joe cotton-poplin shirt

$335

Tkees

x Nili Lotan flip flops

$125

TKEES

Ralph Lauren

ruched wool maxi dress

$1795

Petar Petrov

The Criminal padded distressed leather jacket

$2750

Neous

Moriah heels

$780

SHOPBOP

Stella McCartney

denim midi-skirt

$750

Veronica de Piante

Gia embroidered grosgrain-trimmed wool-twill vest

$1995

Massimo Dutti

straight fit midi skirt

$449

MASSIMO DUTTI

Studio Amelia

Maverick croc-embossed leather boots

$650

MODA OPERANDI

Source Unknown

Geva faded lambskin bomber jacket

$745

SOURCE UNKNOWN

Stella McCartney

asymmetric draped top

$975

STELLA MCCARTNEY

Staud

Masonry pants

Khaite

Nevada leather ankle boots

$1550

Staud

leather Marino jacket

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Lessons in Layering

On days when the weather is crisp and cool one day and warm and humid the next, you’re going to need a strong starting lineup of layering essentials. Our favorites include lightweight jackets that can be easily taken off and put back on; knitwear that you can drape around your shoulders or tie around your waist, and crisp shirting that adds polish regardless of its closet cohorts. When it comes to transitional footwear, kitten heels are another must-have in our early-fall wardrobes.

Nili Lotan

Paola cotton-blend jacket

$1150

Levi’s

low loose jeans

$108

LEVI’S

Aeyde

Perrine glossed-leather pumps

$435

Mango

leopard knit cardigan

$60

MANGO

Banana Republic

Luna cashmere sweater polo

$130

Jacquemus

La Jupe Tozzi zebra-print midi skirt

$2355

Bally

leather blazer

$2035

Aesther Ekme

Lune mini leather shoulder bag

$485

Proenza Schouler

Anneliese dress

$2690

PROENZA SCHOULER

Aeyde

Arla leather knee boots

$595

Cos

short trench coat

$170

Saint Laurent

leopard-print shoulder bag

$2990

FWRD

Banana Republic

oversized shirt

$90

Loulou Studio

wool wide-leg pants

$310

Nour Hammour

Drey leather jacket

$1555

NEOUS

Jumel leather sandals

$760

Slvrlake

oversized denim jacket

$470

Toteme‎

leather midi skirt

$1690

Victoria Beckham

Body Twist T-shirt

Maison Margiela

tan Tabi ballerina flats

$890

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Pre-Fall Flings

Thanks to pre-fall collections from Saint Laurent and Chloé, our dresses and skirts for fall are slinkier–and sultrier–than ever. Styling-wise, juxtapose the romance ever so slightly with a tailored button-up. Suede accessories end on a textural note.

Tove

Damita striped shirt

$645

DÔEN

Elowen lace-trimmed midi skirt

$330

Veronica Beard

Catherine leather mules

$350

VERONICA BEARD

DeMellier

New York suede bag

$756

La Ligne

Ben oversized silk, wool and cashmere-blend polo sweater

$295

The Garment

Tilda tailored wide pants

$375

Jeffrey Campbell

Yachting Day boat shoes

$148

FREE PEOPLE

Veronica de Piante

Kate textured-leather coat

$5795

Chloé

classic cotton gabardine trench coat with cape

$4090

24S

The Row

leather loafers

$1150

Dries Van Noten

asymmetric jersey tank

$215

Chopova Lowena

June carabiner midi skirt

$1210

ssense

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Sometimes Going Back to Basics Is Best

There’s a reason black ballet flats are beloved amongst all fashion girls. They’re the ultimate blank canvas, pairing well with everything from playful, patterned midiskirts to plain tank tops. Bonus points if you step into yours with a bright white crew sock.

Toteme

high-rise satin wide-leg pants

$600

Uniqlo

cotton shirt

$40

UNIQLO

The Row

Boheme MJs

$990

THE ROW

Comme Si

The Agnelli Socks

$30

COMME SI

Nili Lotan

Kedem waxed parka

Levi’s

501 original fit jeans

$98

LEVI'S

Anderson’s

black skinny oval buckle belt

$135

SAINT LAURENT

Aston suede-trimmed sneakers

$925

Polo Ralph Lauren

checked cotton shirt

$170

Cos

pleated A-line midi skirt

$190

STAUD

Becks suede loafers

$365

Staud

Corrine suede jacket

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Add Some Fashion Flare to Your Flats

Crystal-embellished flats are back and better than ever this fall, adding a playful pop to even the most pared-back outfits. Here, opt for a caramel-colored ladylike jacket, capris, and a roomy tote to tie it all together.

Veronica Beard

Lyssa collarless jacket

$598

VERONICA BEARD

FAIT PAR FOUTCH

Marie flared capri pants

$220

Alaïa

leather Mary Jane flats

$1290

Loewe

Puzzle fold leather tote bag

$1900

By Malene Birger

Tinley double-breasted sweater

paneled midiskirt

Cos

wool-trimmed car coat

$290

Le Monde Beryl

Patent-leather loafers

$595

Staud

Eiza dress

$395

Toteme

tumbled trench coat

$1350

Gucci

Horsebit ankle boots

$1270

gucci

Proenza Schouler

Slide suede shoulder bag

$790

Róhe

pailette midi-skirt

$760

Larroudé

Amal mules

$330

SHOPBOP

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How to Upgrade Your Denim Game

A straight-leg blue jean is one of those wardrobe essentials that truly stands the test of time. This fall, however, we encourage you to up your denim game with a few playful styling tips. Start by adding some sequin and shine by layering a sheer midiskirt over your jeans. Then, complete the look with a pop of red by way of a striped tee or kitten heel.

Madewell

Slub boxy-crop tee

$58

Cos

Arch jeans

$135

Gabriela Hearst

Highland lace dress

$3990

GABRIELA HEARST

H&M

leopard ballet flats

$18

H&M

Nili Lotan

Chesney denim jacket

$725

NILI LOTAN

A.P.C.

Elisabeth jeans

ssense

Róhe

wool and cashmere-blend sweater

$550

Haikure

studded denim skirt

$519

Khaite

Roth belted long trench coat

$2900

Dries Van Noten

leather loafers

$895