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Live the Gossip > Lifestyle > My Late-Summer Packing List Easily Transitions Into Fall Thanks to These 3 Style Staples — from $19
Lifestyle

My Late-Summer Packing List Easily Transitions Into Fall Thanks to These 3 Style Staples — from $19

Written by: News Room Last updated: August 29, 2026
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Including lightweight layers, flowy pants, and easy-to-throw-on shoes

Credit: Amazon (3) / People

Late-Summer Packing Essentials

  • Easy Everyday Pants: Gap Wide-Leg Linen Pull-On Pants, from $40 (orig. $70)
  • Up to 51% Off: Gap Poplin Big Shirt, from $34 (orig. $70)
  • $19 Pants That Feel Like PJs: Wiholl Smocked High-Waisted Harem Pants, $19 (orig. $30)
  • Cute Lightweight Layer: Gorglitter Sheer Knit Poncho Top, $39
  • Compared to Birkenstocks: Project Cloud Leather Cork Footbed Slide Sandals, $38
  • High-End Deal: Free People Classic Stripe Pullover, from $69 (orig. $98)
  • Ultimate Summer-to-Fall Shoes: Project Cloud Cork Footbed Clogs, $40 (orig. $45)

When September rolls around, I always want to break out cable-knit sweaters and drink piping hot pumpkin spice lattes, but the East Coast weather reminds me that summer isn’t fully finished.

I just took a late-summer trip to the Hamptons, where I had to plan for warm days and chilly evenings — a reality that will last now through early fall. In turn, I narrowed down my packing list to three key essentials: lightweight layers, long yet flowy pants, and comfy, easy-to-throw-on shoes. If you’re planning an end-of-season getaway or simply want to add practical staples to your in-between weather wardrobe, browse through my list of essentials from Gap, Free People, Puma, and more featured in Amazon’s fashion department.

Pack: Lightweight Layers

Gorglitter Sheer Knit Poncho Top

Credit: Amazon
Credit: Amazon

$39 at Amazon

Ponchos were a staple in my closet as a kid, so I was very pleased to see their resurgence this year. This green poncho has been such a fun addition to my late-summer wardrobe; it’s made from a sheer, lightweight knit that’s breezy enough to wear during the day, yet substantial enough for cooler evenings when I want something over my shoulders. I’ve layered it over tees, tanks, and dresses, and it always adds a fun, polished touch to my outfits.

Gap Poplin Big Shirt

Credit: Amazon
Credit: Amazon

$70 $34 at Amazon

Free People Classic Stripe Pullover

Credit: Amazon
Credit: Amazon

$98 $69 at Amazon

Related: A Style Expert Revealed the No. 1 Fall Shoes That Have More ‘Staying Power’ Than Dated Picks — from $40

Pack: Flowy Pants

Gap Wide-Leg Linen Pull-On Pants

Credit: Amazon
Credit: Amazon

$70 $40 at Amazon

These Gap linen pants have also been a workhorse in the last two months — and I’m not putting them away quite yet. I tend to run hot, so a breathable fabric like linen or cotton is a must for me. These airy pants — which look so similar to a pair we just saw on Anne Hathaway — have a light feel, but their long, wide-legs provide coverage from both the blazing sun and chilly breeze. They also have an elastic waistband with an adjustable drawstring that makes them feel like loungewear, all without sacrificing a polished look. 

Wiholl Smocked High-Waisted Harem Pants

Credit: Amazon
Credit: Amazon

$30 $19 at Amazon

Levi’s 94 Baggy Wide-Leg Jeans, $36 with coupon

Credit: Amazon
Credit: Amazon

$85 $36 at Amazon

Pack: Throw-on-and-Go Shoes

Project Cloud Leather Cork Footbed Slide Sandals

Credit: Amazon
Credit: Amazon

$38 at Amazon

I practically live in my Birkenstock sandals and clogs at this time of year, since I don’t want to rely on flimsy flip-flops but am not quite ready to break out boots. Luckily, I spotted discounted styles from a more affordable brand that multiple reviewers compare to the pricier big-name. 

These sandals, for instance, have a similar cork footbed, tractioned rubber outsole, and thick, wide toe band with an adjustable buckle. One reviewer who dubbed them “extremely comfortable” shared, “They look just like my Birkenstocks, and the quality is impressive for the price… These have a soft, cushy footbed rather than the firm, contoured one you get with Birkenstocks.”

Project Cloud Cork Footbed Clogs

Credit: Amazon
Credit: Amazon

$45 $40 at Amazon

Puma Speedcat Og Lace-Up Sneakers, $95 with coupon

Credit: Amazon
Credit: Amazon

$100 $95 at Amazon

Related: Taylor Swift’s Dreamy $798 Ruffled Dress Sold Out Instantly (Of Course), so We Found Inspired Styles from $36

I spotted so many late-summer and early-fall style staples for travel and everyday wear in Amazon’s fashion hub. Beef up your closet with pieces from $19 now. 

We independently evaluate all recommended products and services. If you click on links we provide, we may receive compensation.

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