Stylists share the wardrobe upgrades worth buying during end-of-summer sales

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End-of-summer sales always catch me at a, shall we say, vulnerable time. By the last week of August, I'm tired of dressing for 90°F weather, but it's far too early to buy a wool coat. Meanwhile, every store is waving clearance prices at me as if I will deeply regret leaving without a pair of lace-trimmed shorts.

The problem is that many of the steepest discounts are attached to clothes whose season is nearly over. So yes, while something may be 70% off, that does not make it a bargain if it goes directly from the shipping box into storage. The smarter move is to seek out pieces you can start wearing now and continue working into outfits once fall arrives.

So how do you separate a useful wardrobe upgrade from clearance-rack bait? We asked personal stylists what they recommend buying from end-of-summer sales, and how they keep a tempting markdown from making the decision for them.

Premium denim tops the list for stylist Shabrina Kara because retailers frequently mark down a wide range of cuts and washes. Rather than buying a highly recognizable trend that may feel dated by next year, she recommends looking for a darker wash that can carry you through fall and remain useful well beyond it.

This is also a good opportunity to replace the jeans you wear constantly but no longer love. A comfortable straight-leg or relaxed pair can work with the sandals and lightweight tops in your closet now, then make the switch to sweaters and boots as temperatures drop.

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Cashmere and jackets are probably not the first things you're itching to buy when it's still hot out. But Kara says late-summer sales are a good time to get them for less. You may not need them today, but that first cool morning will come eventually.

Personal stylist Lilly Beltran recommends choosing a layer that works with at least five pieces you already own. A versatile blazer, for example, will earn its place in your wardrobe far more quickly than a dress bought for a hypothetical party that never makes it onto your calendar.

This does not mean you need to start wearing heavy layers in August. A lightweight cardigan can come along to an aggressively air-conditioned office or restaurant, while an unlined jacket can make a summer outfit feel more appropriate once the calendar turns to September.

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Banana Republic Stretch Twill Classic Blazer

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The sundress section may have the most dramatic markdowns, but buying something with only a few weeks of useful weather left is not always the win it appears to be.

Kara recommends looking instead for transitional dresses that are made from heavier cotton or offered in darker prints. Wear one with sandals while it's still hot, then add boots and a jacket later in the season. The right dress should work in both instances without requiring an entirely new supporting wardrobe.

Tops may not feel as exciting as a new dress or pair of shoes, but Kara considers them one of the most useful sale categories. They are also frequently the reason certain pants get worn while others remain buried beneath the laundry you intend to fold eventually.

Her rule is to have at least three tops that work with every pair of jeans, trousers or other bottoms you wear regularly. You don't have to follow that formula exactly, but it can reveal what's missing. If you own great pants but never know what to wear with them, another pair probably won't solve the problem. A breathable button-down works on its own now and under a sweater later, while a short-sleeve knit gives you a little more coverage now and will work in the fall as well.

When shoes go on sale, it's easy to buy another black pair because you know they'll match existing outfits. But Kara recommends taking advantage of markdowns to explore equally versatile shades such as tan, chocolate or burgundy .

Those colors still work with many wardrobe basics, but they can change the feel of outfits you've already worn dozens of times. Rich brown and burgundy are especially useful heading into fall, when they pair easily with darker denim and seasonal prints.

A matching set can be a smart sale purchase, provided you would wear both pieces separately. Personal stylist Jenni Smith recommends looking for comfortable fabric that resists wrinkles, along with a cut that works for your body.

Smith suggests wearing the top with jeans, then pairing the bottoms with a tee and jacket. If both pieces work with clothes you already own, you will get much more mileage out of them.

The trendiest items are frequently the first to receive deep discounts, and that's not necessarily a coincidence. Kara points to balloon pants and lace-trimmed silky shorts as examples of pieces that may feel very specific to summer 2026. "If you only wear something for one season, it's not a bargain," she says.

Her broader sale philosophy is just as straightforward: "Never let the discount make the decision for you." Before buying anything, she recommends seeing whether you can make three outfits with it using clothes you already own. If nothing comes to mind quickly, it may spend the next year in your closet with its tag attached.

That doesn't mean every purchase must be a sensible, neutral basic. If you love a trend and can already picture yourself wearing it next year, the sale may be your moment. Just make sure you want the clothing more than you want the satisfaction of seeing how much you saved.

The most useful wardrobe upgrade may already be hanging in your closet. Beltran says people often overlook tailoring, even though improving the fit of an existing piece can make it far more wearable.

She also cautions against assuming the lowest-priced basics will save you money. Check the fabric and construction before buying. A shirt that pills after a few washes or loses its form almost immediately isn't much of a deal if you need to replace it before the next end-of-summer sale rolls around.