Fall fashion may already be arriving, but summer isn’t over. The case for dressing for the season you’re actually in—and letting September exist somewhere in between.
By late August, I feel a sense of whiplash. The temperature still says summer, but seemingly everything else has decided we’ve moved on.
Fall collections fill the stores. Boots replace sandals in our feeds. Pumpkin-flavored everything begins its annual takeover. Suddenly, we’re being told to start thinking about sweaters while many of us are still checking the forecast for our next beach day.
I was reminded of just how absurd the timeline has become recently when I needed a new bathing suit.
It was the middle of August. Surely, I thought, if anything, this would be the perfect time to find one on clearance.
Nope.
Summer had essentially been cleared out and shipped away. In its place? Halloween.
Halloween. October 31. More than two months away.
There I was, still very much planning pool and beach days, looking for a bathing suit while retail had apparently decided I should be thinking about pumpkins and costumes.
The funny thing is, I genuinely love fall. I’m a seasons person. I don’t need endless summer or year-round paradise. I like the distinction between one season and the next: the first crisp day, the changing leaves, pulling out a favorite coat after months away. Even winter has its place.
Which is exactly why I don’t understand the desire to skip ahead.
There will be plenty of time for fall. For now, I’m dressing for the season—and the weather—I’m actually in.
Dress for the Weather, Not the Marketing Calendar
Fashion loves a new season. By August, fall has already arrived at retail even if it hasn’t arrived outside your window.
But interestingly, the actual fashion conversation is more nuanced than the merchandising calendar suggests.
Pre-fall doesn’t demand an overnight wardrobe change. Transitional dressing is exactly what its name suggests: pieces that can live somewhere between seasons. Denim, white, lightweight knits, dresses that can take a layer, transitional jackets and pieces that work differently depending on how they’re styled.
That’s much closer to how I actually dress.
I’m not packing away my summer wardrobe because September appears on the calendar. If it’s warm, I’m still taking advantage of the way crisp whites and bright colors pop against the last of a summer tan. I’m still wearing sandals because you certainly won’t find me trying to make open-toe shoes happen in the middle of a New York winter.
Linen pants aren’t suddenly irrelevant. Neither is a great crochet piece. Denim becomes even more useful. Breezy knits start entering the rotation. A jacket, cardigan or blazer gets thrown over something that, a few weeks earlier, stood perfectly well on its own.
Denim is particularly good at this because it doesn’t really belong to one season. A pair of jeans can sit beside a tank in August and a knit in October without feeling out of place. Lightweight knits accomplish something similar, bringing texture and a suggestion of what’s coming without requiring us to dress for temperatures that haven’t arrived yet.
And as for the old prohibition against white after Labor Day? We’ve moved well beyond that.
I’ll happily keep wearing mine.
Let September Be September
Labor Day has somehow become an unofficial expiration date for summer, but September doesn’t have to choose a side.
In New York especially, it can be 80 degrees one afternoon and cool enough for a sweater by dinner. Rather than treating that unpredictability as a wardrobe problem, I think it’s one of the most interesting times to get dressed.
This is when summer pieces start mixing with the first hints of fall. Keep the white trousers, but swap the raffia bag for leather. Wear the dress again, this time with a cardigan. Pair linen with denim. Add a lightweight knit when the evening calls for it. Sandals stay in rotation until the weather—not the calendar—says otherwise.
For me, that’s what transitional dressing should actually mean: transition, not replacement.
It also means you don’t need an entirely new wardrobe just because retailers have moved on to the next season. Some of the best transitional pieces are probably already hanging in your closet.
And the same applies beyond fashion. September can hold onto the last beach afternoon while giving us the first cool evening. We can eat outside while the weather still allows it and look forward to foliage without pretending it’s already here.
The in-between isn’t a season we need to hurry through.
It might actually be one of the best parts.
Maybe September Is the New Summer
Perhaps nowhere is our arbitrary definition of summer more obvious than travel.
For generations, July and August have represented the quintessential European summer vacation. Which is exactly why they’re also the most crowded, the most expensive and often the least relaxing version of the destinations people are chasing.
Now travelers are increasingly questioning whether peak summer is actually the most desirable time to go.
September changes very little about a place and potentially quite a lot about the experience of being there. The Adriatic doesn’t cool down on September 1. The cafés in Dubrovnik don’t get less charming. What can begin to disappear are some of the conditions that make peak-season travel exhausting: extreme crowds, intense heat, impossible reservations and the sense that an entire destination is operating beyond comfortable capacity.
Of course, September isn’t universally the “best” month to travel. Weather and seasonality vary enormously by destination, and as shoulder-season travel becomes more popular, some of its traditional advantages may shrink.
But it does challenge an assumption worth reconsidering:
Who decided the best part of summer has to end in August?
Maybe the smartest trip isn’t always the one everyone else is taking at exactly the same time.
Fall Will Come. Let It.
Soon enough, there will be a morning when the air genuinely feels different.
And I’ll be excited about it. I’ll want the sweaters, foliage, boots and everything else that makes fall feel distinctly like fall. The sandals will naturally move to the back of the closet, the coats will come out, and none of it will require a date on the calendar—or an Instagram trend—to tell me it’s time.
Until then, I’m keeping summer.
Because come March, after months of a New York winter, I know exactly what I’ll be wishing for: a warm afternoon, dinner outside, bare shoulders, a swim, sunlight that lasts well into the evening.
The very things that are still here now.
Maybe one of the quieter luxuries of life is simply letting each season finish its sentence before we start writing the next one.
