Style Stop
By Linda Peavy
End-of-summer sales are here, but before you fill your shopping cart with deeply discounted sundresses, swimsuits, and sandals that may only get another few weeks of wear, think ahead.
Late summer is a great time to shop strategically. Look beyond the price tag and search for versatile pieces that you can wear during these final warm days and transition effortlessly into fall. The key is choosing colors, fabrics, silhouettes, and layering pieces that work across both seasons.
Here are 10 pieces worth looking for as you shop the end-of-summer sales, and two ways to wear each one.
- The Crisp White Shirt

Few pieces work harder in a wardrobe than a crisp white button-down shirt. Look for one with enough structure to look polished but enough room to layer comfortably.
Wear It Now: Roll up the sleeves and wear it open over a tank or camisole. Pair it with a colorful maxi skirt, cropped trousers, or your favorite denim.
Wear It This Fall: Button it up and layer it underneath a blazer, cardigan, or jacket. Let the collar and cuffs peek out for a classic, pulled-together look.
2. The Colorful Maxi Skirt

Don’t assume that a colorful maxi skirt is strictly a summer piece. Look for prints that combine brighter shades with deeper colors such as burgundy, chocolate, navy, rust, olive, plum, or deep green.
Wear It Now: Pair it with a lightweight solid-colored top, tank, or white shirt and your favorite sandals.
Wear It This Fall: Pull one of the darker colors from the skirt and pair it with a sweater, cardigan, or blazer. Add loafers, flats, or boots to completely change the mood.
- The Lightweight Cardigan or Shrug

A lightweight cardigan or shrug is one of those pieces you’ll be glad you bought when temperatures start changing. It also solves the problem of chilly restaurants and overly air-conditioned buildings right now.
Wear It Now: Layer it over a sleeveless dress, tank, or camisole when you want a little extra coverage without adding too much weight.
Wear It This Fall: Wear it over a blouse or dress, or pair it with trousers and denim. Choose a neutral or rich color that coordinates with several pieces already in your wardrobe.
4. The Denim Jacket

The denim jacket has earned its place as a year-round wardrobe staple. If you find a great one during the summer sales, grab it, especially if the fit and wash are right.
Wear It Now: Throw it over a maxi or midi dress for cooler evenings, or wear it with a skirt and lightweight top.
Wear It This Fall: Pair it with fall trousers, maxi skirts, dresses, and deeper seasonal colors. Try denim beyond traditional blue, too; black, cream, olive, or another neutral can make the jacket feel completely different.
- The Lightweight Blazer

A blazer instantly makes an outfit look more intentional. For transitional dressing, avoid anything too heavy and look for breathable fabrics and a comfortable fit through the shoulders and arms.
Wear It Now: Push or roll up the sleeves and wear it over a tank, camisole, or lightweight tee with a skirt or trousers.
Wear It This Fall: Layer it over your crisp white shirt, blouse, or lightweight knit. Pair it with jeans or trousers and add a statement necklace, scarf, or brooch.
- The Midi Dress

A great midi dress doesn’t have to disappear when summer ends. Pay attention to the print and color palette. A dress containing both neutral and deeper hues can transition beautifully between seasons.
Wear It Now: Keep it simple with sandals, jewelry, and a summer handbag.
Wear It This Fall: Add your denim jacket, lightweight blazer, cardigan, or shrug. Trade the sandals for loafers, flats, or boots and introduce a fall handbag.
- The Statement Blouse

End-of-season racks can be a great place to find beautiful blouses. Instead of automatically reaching for neutrals, consider a bold print, an interesting sleeve, a rich jewel tone, or a distinctive detail.
Wear It Now: Let the blouse be the star. Pair it with a simple skirt, lightweight trousers, or denim.
Wear It This Fall: Layer it under a blazer or cardigan, letting the color, print, collar, or sleeves add interest to your fall basics.
- The Wide-Leg Trouser

Look for lightweight wide-leg trousers with enough structure to carry you beyond summer. Neutral colors are versatile, but don’t overlook chocolate, olive, navy, camel, or other deeper shades.
Wear It Now: Pair them with a sleeveless blouse, tank, or crisp white shirt and sandals.
Wear It This Fall: Add a lightweight sweater, blazer, or cardigan and switch to loafers, flats, or boots. Your summer trousers suddenly become part of an entirely different outfit.
- The Neutral Oversized Handbag

Summer sales aren’t only about clothing. A beautiful handbag in a seasonless neutral can be one of the smartest purchases you make.
Wear It Now: Carry a roomy bag in cognac, camel, chocolate, cream, black, or another versatile neutral with your summer dresses and separates.
Wear It This Fall: Use the same bag to pull together your deeper fall colors, jackets, sweaters, denim, and boots. A substantial handbag can instantly make a lightweight outfit feel more appropriate for the new season.
10. The Lightweight Scarf or Wrap

A beautiful scarf or wrap gives you color, texture, and versatility without requiring an entirely new outfit. Look for prints that mix summer shades with richer fall tones.
Wear It Now: Wear it loosely over your shoulders with a sleeveless dress, tie it around your neck, or even use it to add color to your handbag.
Wear It This Fall: Layer it over your blazer, denim jacket, cardigan, or dress. Pull one of the deeper colors from the print into the rest of your outfit to create a more autumnal look.
Hot Summer Sales
Try these hot summer sales on the featured designs:
Shop the Sale, but Think About Fall
A 60% or 70% discount isn’t a bargain if the piece hangs in your closet for the next nine months. As you browse the end-of-summer sales, ask yourself a different question: Can I wear this now and style it differently when fall arrives?
Look for transitional fabrics, layerable silhouettes, versatile neutrals, and prints that incorporate deeper hues. Think about what you already own, a great blazer, denim jacket, cardigan, handbag, pair of boots, or crisp white shirt may be all you need to transform a summer piece into a fall look.
The best end-of-summer purchase isn’t necessarily the one with the biggest markdown. It’s the one you’ll still be excited to wear when the temperature starts to drop.
