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Fall Fashion Lookahead: A One-and-Done Dress, Comfy Pants and More Transitional Staples

Ease into fall with these stylist-picked pieces.

It might not feel like it outside, but fall will be here before we know it. Personally, I can’t wait for the seasons to change, because in my book, there’s no better time of year for fashion.

If you’re not quite in the “pumpkin spice” mood yet, consider this your soft launch into fall fashion. To share pieces that can take you from the final days of summer into the early days of fall, stylist and fashion expert Jasmine Snow paid a visit to Jenna & Sheinelle, bringing with her new trends and tried-and-true staples alike. From lightweight outerwear to a one-and-done dress, you can begin to incorporate these pieces now and transition with them into the new season.

Shall we get excited about the impending sartorial shift? Just keep scrolling to shop Snow’s full roundup of the best fall fashion.

Fall fashion favorites seen on TODAY with Jenna & Sheinelle

Yousify Casual Lightweight Hooded Windbreaker

According to Snow, windbreakers are trending big time. The outerwear makes for the perfect transitional layer in her book, because it’s lightweight enough for late summer but gives you a little coverage once it starts to get cooler in the fall.

“There’s so many ways to style this look — we’re seeing people wear these zipped all the way up, almost like a top, which makes the jacket itself the fashion moment,” Snow says. “Pair it with a wide-leg pant or jeans to make it feel less ‘gym class’ and more ‘street style,’ or pair with leggings for a sportier look ... Such a fun option for football season, fall sporting events or running errands. I love the neutral shades, or use it as an easy pop of color.”

Snow styling the Yousify Casual Lightweight Hooded Windbreaker in White
Snow styling the Yousify Casual Lightweight Hooded Windbreaker in White Courtesy Jasmine Snow

H&M Tie-Detail Shirt Dress

Who doesn’t love a one-and-done outfit? This polished shirt dress is exactly that, creating the illusion that you put a lot more effort into your look than you actually did. A true transitional piece, Snow says you can wear it now with sneakers or a flat sandal, then add loafers or boots and layer with a sweater or jacket once fall arrives.

Snow styling the H&M Tie-Detail Shirt Dress
Snow styling the H&M Tie-Detail Shirt DressCourtesy Jasmine Snow

KBB by Kahlana Women's 'The Hourglass Button-Down Shirt'

H&M Women's Cotton Peplum Shirt

The classic white button-down shirt is getting a makeover this season! Instead of oversized and boxy silhouettes, Snow says she’s seeing more waist definition with peplum shapes and hourglass tailoring. While it’s still a versatile closet staple, the result is that the modern-day staple feels softer, more feminine and much more flattering.

“I love pairing it with something slightly looser on the bottom, like relaxed denim or wide-leg trousers to balance the silhouette — the contrast keeps the look cool and modern,” Snow explains. “I always love a classic with a twist — and these styles still give you the versatility of a classic white shirt, with details that make it feel much more special. Wear to work, to dinner or for an everyday look.”

Halara High Waisted Wide Leg Baggy Casual Pants with Pockets

Old Navy High-Waisted Satin Track Pants

Snow is calling it now: the “it” pants of the season are anything in earthy colors and wide-legged satin fabrics, which feel elevated enough for work but comfortable enough for everyday life.

“These track pants are a more polished take on the sporty look — the satin finish instantly elevates them, so you can wear them with a tank and sneakers for a more casual look or dress them up with a crisp button-down and heels or flats,” Snow suggests. “They are lightweight, which is exactly what you want during that in-between period when the calendar says fall but the temperature still says summer — you can wear now and swap in a button-down, sweater or blazer as the weather cools.”

Snow in the Old Navy High-Waisted Satin Track Pants in Toasted Almond
Snow in the Old Navy High-Waisted Satin Track Pants in Toasted AlmondCourtesy Jasmine Snow

Divanne Buckle Suede Mule Loafers

QIY Mule Loafers

Snow’s pro styling tip? Swap your sandals for a loafer mule, and your summer outfits immediately start to feel more like fall. For the upcoming season, Snow says the biggest footwear trends are “all about flats that feel more refined.” Loafer mules and pointed-toe slides like these fit the bill, making any outfit look more polished without sacrificing comfort.

Snow in the QIY Mule Loafers (left) and Divanne Buckle Suede Mule Loafers (Right)
Snow in the QIY Mule Loafers (left) and Divanne Buckle Suede Mule Loafers (Right)Courtesy Jasmine Snow

More expert-approved fall fashion

Doublesoul Low 3-Pack Basic

Remember the great crew-versus-ankle-sock debate of 2024? While we debated the topic internally at the time, we’re ready to put the argument to bed once and for all: Shop TODAY officially claims team ankle socks. The cushy staple exposes a flash of your lower leg that brings balance to shorts, capri pants and skirts, all of which we’ve been rocking on repeat as summer draws to a close.

Los Angeles Apparel Baby Rib 3/4 Sleeve Boatneck Top

If you feel like you’ve been seeing this classic style of top everywhere lately, your eyes don’t deceive you — according to Google Trends data, searches for “boatneck top” and “3/4 sleeve top” have spiked in the last few months. I think the essential makes for the perfect transitional piece, since it can be worn on its own now and layered up when temperatures drop.

Zara Cotton Button-Up Sweatshirt

A polished piece that secretly feels like sweats? Sign me up. This cardigan-esque layer is truthfully more like a sweatshirt than a proper cardigan, but it hardly looks that way to outsiders.

H&M Chunky Sneakers

Another comfort-forward trend, Snow co-signs the chunky sneaker craze. This pair she likes from H&M even marries two trends in one, given that butter yellow has been on the rise in the last few years.

Zara High Waisted Wide Leg Jeans With Darts

I previously dabbled in the skinny jean trend, but if I’m being honest, my heart just wasn’t in it. For me, the baggier the pants, the better. These high-waisted, wide-leg jeans are constructed almost like trousers, offering a roomy fit with a polished pleated look that feels like a step up from your typical slouchy, baggy denim.

Mango Double-Breasted Micro-Houndstooth Jacket

Asos Design Power Shoulder Double Breasted Blazer

Consider this staple your instant outfit upgrade to channel big boss energy. Featuring exaggerated shoulders and a double-breasted design, these blazers are your one-stop shop to get in on the “power dressing” trend that’s been going strong for a few years.

Meet the expert

Our team features a range of qualified experts and contributors in our broadcast segments to reveal the latest in trends, remarkable sale events and all things shopping across a variety of categories. Products were independently chosen by members of the Shop TODAY team, along with Jasmine Snow.

How we chose

The Shop TODAY editors and writers search the internet to find the best products out there. We interview expert sources, comb through customer reviews and even use our own personal experiences to make shopping easier for our readers.

As an editorial team, we independently create content and determine coverage based on research, reporting and what we think TODAY.com readers would like to read about. The goal of our content is to provide a service and inform readers on the hunt for the latest products to help improve their lives. Items are sold by retailers, not TODAY. Pricing and availability are accurate as of publish time.

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