Best Summer to Fall Street Style 2019

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Seasonal dressing is pretty straightforward. We can probably all agree that we don’t want to be wearing a cashmere sweater in 90 percent humidity, right? On the other hand, transitional dressing — that particular time of year when it feels like even my weather app and local meteorologist can’t prepare me for the extreme temperature variance — is confusing, but with that confusion also comes opportunity. Here, between the lines — or seasons, rather — things get more unpredictable, more playful. We don’t want to go straight from Summer sundress and sandals territory to a sweater dress, tights, and ankle boots, and we don’t have to. There’s room for ad-hoc layering, the freedom to wear a pantsuit with, say, slides and without socks; the sweet satisfaction of juxtaposing major Summer trends with classic Fall staples, and vice versa.

You wake up to outfit possibilities with every daily forecast — will a balmy 81 degrees turn to a downright chilling 64 degrees at sunset? You bet! So go forth and throw a blazer over that crop top or slip into high-waisted trousers and a sleeveless knit and mules. And if you’re struggling to get it together, all you need to do is mix it up — herein, 125 outfit ideas that’ll work when the weather starts to change and all you want to do is look and feel cute. We’ve got you covered.

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