October 2, 2023


Unique & Classy

9 Transitional Outfits That Carry Over to Fall Fabulously

4 min read

All these and more transitional outfits that will bring you into the new season with elegant ease, below.

The Autumnal Maxi Dress With a Transitional Trench Coat

Esse Studios organic cotton-poplin maxi dress

We’re not asking you to give up on your summer wardrobe entirely. Case in point: this bustier-inspired maxi dress from Esse Studios. For fall, style the staple with Massimo Dutti’s full-length trench coat and a simple pair of fashion flats from Vince. The Row’s Half Moon bag is a perfect match, while dainty jewels from Joolz by Martha Calvo and Lié Studio will shine all season long.

Massimo Dutti trench coat

Vince Leah leather ballet flats

Esse Studios organic cotton-poplin maxi dress

The Row Half Moon leather shoulder bag

Joolz by Martha Calvo Libre 14kt gold-plated necklace

Lié Studio The Julie gold-plated earrings

The Suit Vest Staple With a Quietly Luxurious Loafer

J.Crew slim-fit tuxedo vest in city crepe

The suit vest sensation is carrying over into fall–and we couldn’t be happier. For a take on modern workwear, style the It item with Hill House Home’s black maxi skirt and a pair of Mary Janes from Mango. Hereu’s two-toned tote makes the perfect work bag; and these everyday treasures from Ben-Amun and Jenny Bird delight and dazzle.

Hill House Home The Delphine Nap skirt

Mango elastic satin ballerinas

J.Crew slim-fit tuxedo vest in city crepe

Hereu Calella cotton-canvas tote bag

Ben-Amun 24K gold-plated necklace

Jenny Bird Puffy Faye knockers

The Lightweight Leather Jacket With a Mesh Ballet Flat

Pixie Market Nash oversized leather bomber jacket

The key to mastering any wardrobe transition is a piece of lightweight outerwear. Enter Pixie Market’s leather bomber jacket. Styling-wise, the rest of the look is kept cool and casual with a pair of baggy jeans from Agolde and By Malene Birger’s timeless tank. The pièce de résistance, of course, is this pair of crystal-embellished, mesh ballet flats from Khaite. Need we say more?

Loulou Studio Limba ribbed organic cotton tank

Agolde low-rise organic boyfriend jeans

Pixie Market Nash oversized leather bomber jacket

Anderson’s textured-leather belt

Khaite Marcy ballet flats

Loewe Puzzle Fold Mini leather tote bag

The Must-Have Matching Set With a Sleek Shoulder Bag

Posse Isabela ruched jersey tank top

Like an all-in-one-outfit dress, a matching skirt set has a similar closet appeal. From Australian-brand, Posse, this chocolate brown set is masterfully minimal and incredibly stylish. Finish off the look with a pair of suede loafers from Emme Parsons and Savette’s sleek shoulder bag.

Emme Parsons Danielle loafers

Posse Isabela ruched jersey tank top

Savette Tondo large textured-leather shoulder bag

Sophie Buhai Ball Drop earrings

Aire Capricornus sunglasses

The Clean-Lined Denim Skirt With a Minimalist Mary Jane

Zimmermann Luminosity denim maxi skirt

No fall capsule wardrobe is complete without a clean-lined denim skirt—and this one from Zimmermann, to be exact. Other prized pieces of this transitional outfit include Staud’s striped shirt, Mary Janes from Aeyde, and St. Agni’s ivory crossbody bag. Earrings from By Adina Edin are not to be ignored, either.

Zimmermann Luminosity denim maxi skirt

St. Agni soft crescent bag

By Adina Eden solid chunky drop stud earrings

The Fall Tailoring Essential With a Quietly Luxurious Loafer

Tibi Hopper checked wool and cashmere-blend blazer

Blazers are forever in style regardless of the season. This upcoming fall, Tibi’s cashmere-blend blazer checks all the boxes. For everyday, wear with Vince’s plain, but perfect white tee, chic cargo pants from Cos, and a pair of quietly luxurious loafers from Tory Burch. Meanwhile, J.Crew’s suede shopper ties the entire ensemble together.

Vince essential crewneck top

Tibi Hopper checked wool and cashmere-blend blazer

Tory Burch classic loafers

J.Crew Berkeley bucket bag

Bottega Veneta gold-tone earrings

The Sleeveless Knit Dress With a (Fall) Fashion Flip-Flop

Polo Ralph Lauren pleated charmeuse midi dress

Knit dresses are a fall fashion favorite for a reason—and this fall, we’re sporting (and shopping!) Polo Ralph Lauren’s sleeveless style. Dainty, yet delightful accessories include Toteme’s cream-colored tote bag, a pair of thong sandals from Zara, tortoiseshell sunnies from Celine, and statement gold jewels from Jennifer Fisher.

Zara rubberized flat sandals

Toteme fold-handle leather bucket bag

Polo Ralph Lauren pleated charmeuse midi dress

Celine Eyewear Triomphe oval sunglasses

Jennifer Fisher Lilly gold-plated hoop earrings

Petit Moments Cher chain necklace

The Denim Delight With a Pleated Maxi Skirt

Each season, there are those closet classics we return to time and again. Somehow, delightful denim always seems to outshine the rest, like this jean jacket from Tory Burch. To style, wear with Reformation’s pleated midiskirt, Vince’s power shirt, and a pair of Adidas Decon sneakers. Meanwhile, basket bags are perfectly appropriate for fall, like this one from Dragon Diffusion.

Adidas Originals Samba Decon sneakers

Dragon Diffusion Triple Jump small woven-leather basket bag

Lexxola Jordy square-frame tortoiseshell sunglasses

The Cozy, Yet Chic Cardigan With a Cargo Pant

Loewe Anagram Intarsia cardigan

For chic, yet cozy coverage, find Loewe’s printed cardigan this pre-fall. Styling tip? Wear it with Vince’s caramel-colored cargo pants and ballet flats from Le Monde Beryl. Fit for fall, finish the look off with Manu Atelier’s suede shoulder bag.

Le Monde Beryl Regency silk-satin slippers

Loewe Anagram Intarsia cardigan

By Alona Luca tiger’s eye & 18kt gold-plated necklace

Panconesi Blowup earrings

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