Same Same But Different: How We’re Dressing for Transitional Weather

Welcome to Same Same But Different. As Gen Z and millennial fashion editors, respectively, we know a thing or two about shopping—for all ages, and especially our demographics. As we find the best products for you, we can’t help but do a little shopping for ourselves and build our personal (age-appropriate) wish lists. And now, we’re sharing them with you. Ahead, check out what’s in our hearts and in our carts lately.

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Dale Chong: Somehow, I breathed and the end of summer was here. And while I do lament the feeling of missing out on all that is warm and carefree (my definition of the season, if you will), I can’t say I’m mad about fall looming. Maybe it’s the fact that I’m over the balmy, sticky, and exhausting heat (my other definition of the season), but I love it just as much as I love summer. That said, the transition between the two—more specifically, dressing for the transition between the two—is a task that typically makes my head tilt. How does one style herself when the temperatures range from the mid-60s to the 90s in one day? Or when one is dealing with the frigid A/C? Or, I don’t know, when one craves breaking out the lug-sole ankle boots but still wants to don her best camisoles and call it a day? Asking for a friend here, obviously. Any thoughts, Meg?

Meg Donohue: I knew I couldn’t be the only one dumbfounded by how fast this year is flying by—glad to hear you’re equally amazed. That said, I’m more miffed about fall’s early onset than you seem to be. I’ve declared (to no one other than myself) that this year I will celebrate summer until fall officially starts on September 23. I typically consider Labor Day weekend the end of summer, but I simply haven’t gotten my fill of the season yet. So I’m bringing summer into September. Who’s with me?

DC: It appears we have a bit of a standoff for this month’s SSBD.

I feel you though; there is always a handful of weeks in September that feel sweltering before fall weather officially rolls in. Until then, I’m incorporating the fall season with an autumnal color palette. At the moment, that takes form in this sheer, textured top from Leinwande—which, to be frank, is a little unexpected for me. Light enough to wear without weighing me down, I’ll be throwing this over a knit tank paired with elevated denim shorts. Pair it with my new favorite sandals and a tiny shoulder bag and I’m good to go.

How will you be pulling all your summer wares into fall?

MD: To recap: you’re bringing fall into summer while I stretch summer through fall. I get it. It’s funny you should mention sheer tops, because I’m thinking it’ll be a big trend in my fall lineup, too. For instance, I’m obsessed with this black midi skirt I recently picked up. You can’t really tell that it’s see-through unless you see it in a certain light or at a specific angle. I think it’ll be key in my crusade to drag out every final summer moment. The color black might not scream summer, but showing a little skin definitely does. I’m also looking for summery silhouettes and color schemes in otherwise cool weather styles. Lastly, you know I love my wedge flip-flops, and I happen to think they’re very well-suited for transitional outfits.

DC: I LOVE those flip flops; they make me think of some I had when I was in middle school, and I’m happy to see them make a return. And on the note of sheer fashion, I have to say, in my humble opinion, it is the ultimate transitional weather look. I mean, just look at how sheer flats have been the unsung hero of the latest shoe trends!

I’d love to know what you have planned for when the temperatures start to drop. As someone who can’t shut up about quality knitwear, I’m eager to start wearing my cozier sweaters again. But, it seems it won’t be cooling down to the 40s any time soon. And as someone who tends to be on the colder side (woe is me), I’m opting for a denim jacket I can easily throw on when the A/C is blasting. I’m taking the opportunity to incorporate fall-esque accessories with my warm-weather staples. In this case, it’s a baby tee (they’re all I’m currently wearing) and a slip skirt with comfortable, investment-worthy boots—and let’s be real: chunky ankle boots are a staple no matter what time of year it is.

MD: I hear you. September always has a few hot days, and I plan to be prepared with the perfect Goldilocks outfit. All summer, I’ve been enamored with this short playsuit that can be dressed up or down. (I’ve even worn it on hikes!) Because it’s black, it will phase seamlessly into autumn styles, but I also envision reaching for this striped button-down to wear as an open-faced layer. Dua Lipa flawlessly showcased how this shirt can be worn for summer, but the lines between late summer and early fall are blurred, so I think I’ll be able to match it to September’s crisp, preppy vibe.

Finally, I know I’m being a bit of a renegade here, but I vote we hold onto the crochet trend just a little while longer. Summer never fails to see raffia and straw bags galore, and why should that end after Labor Day? Call me crazy, but I’ll be using my favorite knit tote throughout September. Care to weigh in?

DC: Despite my crusade for fall fashion now, I am admittedly a fan of embracing summer trends for colder weather. Crochet is a great example. I personally feel the same about the fashion “rule”—which, let’s be honest, there are no rules in fashion these days—about not wearing white after the September holiday. I’m also a fan of fall and winter whites. Sue me!