Happy fashion month to all who celebrate! The fashion industry's Super Bowl will soon kick off, and speaking for myself only, I am nowhere near prepared. My closet is still fully in white-tank-and-baggy-jorts mode (read: the factory setting its been in for the last three months) and has not been optimized for summer-to-fall transitional dressing—let alone elite runways and swarms of photographers.
Even if you don't have any fashion shows on your calendar, I'd bet you probably still have at least a few Feeld dates, outdoor weddings, or job interviews you need to dress for. And let's be honest, those events can be even more high stakes than a fashion week show. So, yeah, your outfit had better be top-level.
But don't worry if you feel underprepared. In order to ease my own outfit anxiety, I dug deep into the NYFW street style archive for cute September outfits for every type of occasion.
Shorts and a Blazer
I refuse to part with my beloved Bermuda shorts, no matter what the calendar says, so I've been on the hunt for ways to wear them into the fall season. As it turns out, my blazer collection is the key. Just pop one on with a luxe silk scarf and a pair of strappy sandals.
A Black Tank and White Skirt
This outfit has reigned supreme the past two summers and it's not slowing down anytime soon. A black tank and voluminous white skirt looks chic and elegant for any occasion—but if you want a more casual vibe, finish with a pair of sneakers.
A Fall Color Scheme
Girls will be like "I need this," and it's just an all-brown outfit and a lavender latte. Fall is within sight, so dust off your favorite autumnal hues—starting with mocha shades favored by Sabrina Carpenter and other celebs.
Leather, Summer-ized
It's not quite leather season yet, but that won't stop us from trying. Try your tiniest dress and a pair of boots to make your favorite fall texture feel appropriate for the last weeks of summer.
A Button-Down and Jeans
Allow me to introduce you to my emotional support outfit—the one I throw on when I'm feeling lazy and uninspired, but still want to feel cool and fashion editor-y. The equation is as follows: baggy jeans + perfectly-oversized graphic tee + bright striped button-down + a pile of mismatched necklaces.
A Tent Dress and Sneakers
In the world of fashion, Ganni is never wrong. Channel their trademark look with a poofy dress and sneakers when you need a casual-cute look that you can walk around in all day long.
Band Tee and Jeans
The secret to making this classic combination look elevated? The accessories. Reach for your absolute slay-est designer bag and a pair of statement shoes to give your most-worn jeans and tee a high-fashion kind of feel.
An Unexpected Sweater Moment
On days when you're dying to dip into your sweater reserve but the weather just won't let you, I recommend knotting one around your waist. Grab one in a contrasting color to add to the eclectic vibe.
A Sheer Tank and Jeans
Pivot your most summery tank top into almost-fall territory with a pair of matching jeans to ease your way back into full-coverage dressing.
Denim and Khaki
Rejuvenate your favorite khaki pants with the addition of several denim add-ons. The two hues may seem kind of random, but wear shockingly well together.
A Rugby Shirt and Micro-Mini
The baggy shirt + micro skirt look is one that's gotten me through more than a few Saturday brunches. A rugby-style top adds an extra dose of prep/tennis vibes.
The First Plaid Dress of the Season
Few things hit harder than the first plaid of the fall season. But since the weather probably won't hit Real Fall™️ temps for another couple months, go for a little plaid dress in a lightweight fabric. Leopard print shoes will make the classic print feel undeniably fresh.
A Breezy Button-Down and Midi Skirt
Now's the time to shift from teeny-tiny skirts to midi and maxi. Try styling with a loose-fit button-up and loafers to make an A-line skirt feel more office-appropriate.
A Short Shorts and Long Jacket
Get a few more wears out of your shortest hemline by layering it under an ankle-length duster jacket for a bit of additional coverage. Go for knee-length boots rather than flats to balance out the cheeky cut.
A Button-Down and Track Pants
Reunited and it feels so good! Finally, your beloved Adidas track pants can return to the fashion lexicon once more—and you won't be separated from them any time soon. Style them for work with a dress shirt and slingback kitten heels.
Kelsey (she/her) is a freelance digital fashion editor and writer with a knack for turning top-performing content into top-selling content. She has extensive experience in editorial and e-commerce strategy, having worked in both divisions during her years at Seventeen and Bustle. With more than a decade of experience in digital media, she also offers creative and social media consulting, as well as copywriting services. She enjoys cheeseburgers, traveling, and vintage hauls. Follow her on Instagram at @klstieg.
