19 Early Fall Outfits Perfect Looks for the Seasons Start 2026

Fall is here, Early Fall Outfits Perfect Looks for the Season-sand it’s time to switch from flip-flops to booties and enjoy cozy fashion. The stylist has experience with many seasonal trends and has worked with both celebrities and regular people to create the best early fall looks.

Oversized Sweater and Leggings

Wearing this classic combo gives both comfort and style, like a warm hug. Adding ankle boots makes it perfect for activities from pumpkin picking to Netflix marathons.

Leather Jacket and Jeans

This timeless duo creates an edgy look while staying casual. It’s perfect for grabbing a pumpkin spice latte without any judgment.

Midi Skirt and Turtleneck

This outfit combines a turtleneck with summer skirts for a sophisticated fall look. It keeps you warm while still holding on to summer style.

Plaid Blazer and Straight-Leg Jeans

Wearing a plaid blazer with straight-leg jeans gives a stylish fall look that feels effortless. It’s great for work or catching the attention of someone special at a coffee shop.

Sweater Dress and Knee-High Boots

Wearing a dress with boots creates a cozy and stylish fall outfit. It feels like a wearable blanket and is perfect for strutting through fallen leaves.

Denim Jacket and Maxi Dress

Wearing a denim jacket over a maxi dress gives summer dresses a fall-ready look. It adds instant autumn vibes while keeping your summer style alive.

Chunky Knit Cardigan and Slim Jeans

This cozy and stylish outfit is perfect for any day when you’re not sure if it’s sweater weather it always is.

Trench Coat and Ankle Boots

Wearing this classic outfit gives a detective-inspired look. It’s perfect for solving mysteries like missing summer clothes or sudden pumpkin cravings.

Flannel Shirt and Leggings

This cozy outfit gives a lumberjack-inspired look. It’s great for apple picking, pumpkin carving, or just pretending to chop wood.

Shacket and Mom Jeans

A shacket is a mix between a shirt and a jacket, perfect for layering. Wearing it with mom jeans gives a relaxed, cool look.

Utility Jumpsuit and Sneakers

This outfit combines style and practicality. It looks ready for anything, whether fixing a car or attending a fashion show.

Corduroy Pants and Crop Top

Wearing corduroy pants with a crop top creates a fall-ready look that still shows a bit of midriff. It’s stylish and seasonal at the same time.

Leather Skirt and Chunky Sweater

Mixing tough and soft textures creates a balanced look that’s both sweet and sassy. It’s perfect for days when you can’t choose just one vibe.

Turtleneck Bodysuit and Wide-Leg Pants

This sleek and chic outfit makes you look put-together. It’s perfect for looking confident, even on days when life feels a little messy.

Silk Slip Dress and Leather Jacket

Wearing pajamas as an outfit works for “I woke up like this” days when you still want to look stylish. Just make sure they’re not your bedtime PJs.

Knit Set (Top and Skirt)

Wearing a matching set feels like a cozy blanket while still looking stylish. It’s perfect for days when you want to be comfortable but put-together.

Puffer Vest and Long-Sleeve Tee

This outfit gives a casual outdoorsy look. It’s perfect for days when you might go hiking—or just to Starbucks.

Plaid Mini Skirt and Tights

Wearing this classic outfit channels a Cher Horowitz vibe, perfect for a fun, school-day-inspired look without the homework or drama. Altogether, these 19 early fall outfits give stylish, playful, and cozy ideas for the season, letting you enjoy autumn with confidence and creativity.