Summer to Fall transitional Outfit Inspo

Who here has ever been in shorts and flip flops at school or the office, hot AF outside but freezing your butt off inside?

It’s not every year we’re graced with a gradual transition from August to September. But this year, rain showers and cool breezes are guiding us gently into autumn, and I’m sooo excited to share some transitional August 31 to September 1 outfit ideas to match the weather!

I’m going to do a little series of transitional looks starring one new look every week until September.

Starting with today’s look: Gladiator sandals and a puff sleeve dress.


This Express puff sleeve dress goes well with a cinch, too. I’ve worn it on vacations in warm weather, and belted with thigh-high boots in Fall!

This puff sleeve, diamond-pattern dress is lightweight and breathes when you’re outside. That’s how I’ve gotten so much use out of it last Spring in South Korea and this summer. But the sleeves add the perfect cover and style to pair it with leggings or boots when the cold weather blows in. My favorite fall style with this cute dress is belted at the waist and paired with over-the-knee boots (flat, no heels).

Psst! This Free People puff sleeve dress is also super cute and autumnal~


I hate my toes but LOVE these shoes. I’ve worn them ALLL summer, and can’t wait to experiment with more fall looks.

Okay, once a season I find ~the shoe~ The one that I end up wearing day after day, with everything, because they’re a) comfy as hell and b) cute as hell. This summer, these leather lace-up gladiator sandals, purchased on a whim at a UO seasonal sale, are ~the shoe~

These shoes are super breathable for your feet, plus the thin sole is great for walking because there’s no unnecessary pressure when you take a step—like walking barefoot (except with protection from the scorching pavement). I’ve worn “comfort” shoes that are less comfortable than these.

Pro Tip: during Hurrican season (starting now) these can withstand puddles and dry out quickly. You know, in case rain boots or galoshes don’t match your outfit.

Next time, I’m trying knee-high gladiator sandals.


Nothing says fall like a palette of reds and browns. Burgundy, the color of these barn doors, is always fashionable in the fall. Photo (C) Amanda Song 2018.

My handbag is a fall must-have, and also transitions nicely. In the summer it can be a little heavy (dark browns are more a fall/winter palette) so I dressed it for summer with a bright flowy dress and strappy sandals. Now, I can take it right into the colder weather by simply adding a leather jacket!

This vintage buckle purse is my mom’s from decades ago, but since they’re so trendy this fall, I’ve found you a similar vintage buckle bag. Just grab it before someone else does!


Shop the look:
Asos puff sleeve shirt dress or Forever 21 trumpet sleeve dress.

Urban Outfitters leather lace-up gladiator sandals or the Asos high leg gladiator sandals.

Poshmark vintage Mexican leather purse.

Thanks for reading as always, and be sure to like + follow for more XOXO