12 Cute Fall Outfits to Make Transitional Dressing a Breeze

It might still be summer, but mentally, we're in sweater-weather mode thinking about all the cute fall outfits to put together as we ease into cooler temps. Transitional looks reign supreme this time of year, making it a veritable fashion playground for mixing and matching pieces from various seasons into your wardrobe.

Not sure where to begin? Start by incorporating summer’s greatest hits into your fall fashion arsenal. A lightweight sun- or shirtdress is a perfect base for playful knits, while chunky footwear—think lug-soled boots or loafers—can instantly ground a long-sleeved midi skirt or dress. Once the forecast truly dips, you can go ahead and rework certain winter wardrobe staples for added contrast: A heavenly soft pullover looks on point when styled with a miniskirt and knee-high boots for going out, while a cropped puffer and matching sweatsuit remains a no-fail combo for days when you want to feel put together with minimal effort.

No matter what vibe you’re going for this fall, the key to building a successful cold-weather wardrobe starts with pieces that offer what fickle temps demand: layers, layers, and more layers—and we rounded up a list of cute fall outfit ideas to prove it. So whether you’re venturing out into an office again or maintaining your work-from-home status, here are 12 cute fall outfits to start planning—and shopping for—now.

Oversized Blazer + Flowy Jumpsuit

Our blazer-wearing days are officially back—and a loose-fit silhouette is a great intro to autumnal dressing. It adds subtle structure to your look, whether paired with flowy jumpsuits or maxi dresses. Beaded chokers keep you in a summer state of mind.

Babaton Agency Blazer

$248.00, Aritzia

H&M Linen Jumpsuit

$50.00, H&M

Anni Lu Weave Dancer Chips & Lemon Necklace

$100.00, Farfetch

Catbird Daisy Chain Necklace

$25.00, Catbird

Midi Dress + Ankle Boots

No need to pack up your favorite summer dress yet—just introduce it to some suede booties. These pieces plays perfectly well together, not to mention that a thick lug-sole is an objectively practical choice for navigating puddles.

Christy Dawn The Plum Dress

$288.00, Christy Dawn

Tory Burch Chelsea 50mm Lug Bootie

$378.00, Nordstrom

Deseda x Linda Baritski Galaxy Love Scarf

$195.00, Deseda

Oma the Label The Liv Hoops

$49.00, Oma the Label

Neon Blazer + Blue Jeans or Black Jeans

A statement blazer is great for dressing up wardrobe basics you already have in your closet. Neon colors, like hot pink, reign supreme this season—and look best worn over cropped white T-shirts and straight-leg denim.

Zara Flowy Straight Cut Blazer

$119.00, Zara

LeScarf No.42 Monogram-Print Silk-Twill Scarf

$90.00, Matches Fashion

X Karla Hanes The Crop Tee

$30.00, Amazon

Levi's Ribcage Straight Ankle Jeans

$80.00, Amazon

Neon Coat + Wide-Leg Jeans

Speaking of retina-burning hues, Granny Smith apple is having a major moment among cool girls and celebs. (You can thank Hailey Bieber's stylist Maeve Reilly for convincing us we need to be wearing our greens, not just eating them.) Reserve the bold tone for coats, blazers, and knits, which you can use to play up the more casual items in your repertoire, like wide-leg denim and white tank tops.

Staud Shoko Colorblock Sweater

$165.00, Nordstrom

Free People Blissed Out Scoop Neck Tank

$28.00, Free People

Agolde Crisscross Jeans

$188.00, Shopbop

New Balance 608v5

$70.00, Zappos

Bomber Jacket + Button-down Shirt

Button-downs and jeans have now entered the chat. This classic pairing will instantly make you feel like your best self—and it's a fall look you can wear on repeat by switching up your styling game. Opt for a bomber jacket with flats if you're headed to brunch with girlfriends. Otherwise, reach for a padded blazer and kitten heels for a sophisticated but low-key date-night look.

Ganni Recycled Nylon Puffer Jacket

$295.00, Ganni

Everlane The Boxy Oxford

$75.00, Everlane

3x1 Kaya Skinny Split Jeans

$330.00, Shopbop

Urban Outfitters Beth Baguette Bag

$39.00, Urban Outfitters

Miniskirt + Knee-high boots

Is it really fall if you don't wear a miniskirt with boots at least once? Add a coat and tights if you have a chilly early morning commute, or swap the knee-length style for shorter, thick-soled booties for a grungier vibe.

Ba&sh Baylor Buttoned Cardigan

$295.00, Ba&sh

Wdirara Split Hem Mini Skirt

$21.00, Amazon

Vagabond Shoemakers Hedda Knee High Boot

$240.00, Nordstrom

Feisedy Vintage Square Cat Eye Sunglasses

$20.00, Amazon

Sweater Set + Statement Bag

A matching sweater dress set is a no-fuss way to make a statement, and you get double the outfit mileage when you wear these pieces separately. Square frames with light-tinted lenses add instant cool—no makeup required.

Reformation Circa Open Knit Two Piece

$248.00, Reformation

Free People Rosemary Sweater Set

$108.00, Free People

JW Pei Gabbi Bag

$80.00, Amazon

Le Specs Glo Getter Sunglasses

$68.00, Amazon

White Button-down + Linen Trousers

Kendall Jenner wore a similar black and white outfit earlier this year, and we totally get why: Between the combined nonchalance of the unbuttoned shirt and the loosely tailored trousers, this is a borrowed-from-the-boys look that's downright cool.

AYR The Deep End Oxford

$135.00, AYR

Leset Classic Margo Tee

$58.00, Revolve

Arket Elastic-Waist Linen Trousers

$69.00, Arket

& Other Stories Croco Leather Belt

$49.00, & Other Stories

Knit Bra + White Jeans

No T-shirt, no problem! Emphasize a deliciously soft cashmere bra with a relaxed open button-down and matching jeans. This kind of tonal outfit is perfect for minimalist tastes, with rectangular shades completing the look.

& Other Stories Oversized Shirt

$69.00, & Other Stories

Frame Le Italien Straight Blanc

$338.00, Frame

Favorite Daughter Sleeveless Crop Sweater Top

$98.00, Nordstrom

Butaby Rectangle Sunglasses

$21.00, Amazon

Sweater Vest + High-waisted Jeans

Humble grandpa knits made their way into our wardrobes last spring, and they're officially back for fall. Embrace texture with an oversized cable-knit: Not only does the tactile material look super cozy, but the sleeveless V-neck silhouette has infinite layering potential over printed mesh tops, turtleneck sweaters, and bodysuits. Style it with high-waisted denim (in a baggy or skinny jean fit) for a look that reads thoroughly modern.

Gap High Rise Barrel Jeans With Washwell

$80.00, Gap

New Balance 990 V5

$185.00, Bandier

Topshop Cable Knit Oversize Sweater Vest

$68.00, Nordstrom

Aurate Medium Chain Necklace

$130.00, Aurate

Cropped Puffer + Sweatsuit Set

On days when you want an outfit that's legit cute but also rain- and sleet-proof, a down puffer will come to the rescue. In a cropped style, this winter essential will serve as a cozy layer atop a matching hoodie-and-sweatpants or leggings set, while still offering aeration thanks to the shorter length. Utilarian and stylish? Say no more.

Entireworld Sweatshirt

$88.00, Entireworld

Entireworld Sweatpants

$88.00, Entireworld

The North Face 1996 Retro Nuptse Jacket

$280.00, The North Face

Le Specs Recovery Sunglasses

$78.00, Amazon

Trench Coat + Flip-flops

A long coat adds instant polish to whatever you're wearing—not to mention it's a fall style staple that transcends any seasonal fashion trends. Try a sleek duster or trench coat that hits just above the ankles for maximum impact and full-body cocooning. Bitter wind? Who's she?

Sezane Scott Trench

$305.00, Sezane

Pilcro The Column Straight Jeans

$128.00, Anthropologie

Buck Mason Pima Cropped Easy Crew

$35.00, Buck Mason

Ancient Greek Sandals Charisma Padded-Strap Leather Flip Flops

$255.00, Matches Fashion

Originally Appeared on Glamour