30 Looks To Help You Master Fall’s Top Trends

Any other year, September’s arrival would signal the beginning of New York Fashion Week, and therefore, an endless array of outfit inspiration from street style. Alas, it’s 2020, and with NYFW promising to be a lot different this year, we now have to look elsewhere for stylish outfits to try this month. Add to that the fact that September weather is confusing and erratic, many Americans are still spending the majority of their time indoors, and young people are reluctantly heading back to school, and chances are, everyone is in for a tricky month of dressing. 

But hope for fall dressing isn’t all lost. In fact, from the look of our Instagram feeds, people are getting more creative with their outfits. Sundresses in fall shades of orange and red, lightweight button-downs with slouchy trousers, and back-to-school trends like loafers, pleated skirts, and sweater vests are all experiencing a rise in popularity as we transition from summer to fall. Clothes are comfier, but all the more stylish, and looks are becoming more authentic to peoples’ individual styles rather than being influenced by the pressures of dressing for fashion month.


Ahead, find 30 pieces of proof that September style still triumphs.

1 of 30
Big, tie-dye button-downs and slouchy pants are the fall quarantine combo we've been waiting for.
2 of 30
It's fashion month — and, even if nothing about fashion looks the same, September's arrival is the perfect excuse to get all dressed up.
3 of 30
We're soaking up the sun and wearing as little clothing as possible for as long as the weather permits.
4 of 30
September's number one quarantine trend: matching your hair color to your dress.
5 of 30
When in doubt, throw on a cowboy hat.
6 of 30
We might not yet be heading back to the office, but that doesn't mean we can't dress up like a boss.
7 of 30
The case for PJs as real clothes has been made — and this look proves that the verdict is in our favor.
8 of 30
Fact: every outfit needs a pair of tinted shades.
9 of 30
Who's seriously excited for puffer coat season?
10 of 30
Check, mate!
11 of 30
The goal here was to fit every trend of the season — button-downs, baguette bags, socks with loafers, and athletic shorts — into a single stylish outfit. Mission accomplished.
12 of 30
We weren't wearing denim this quarantine — until we saw this look.
13 of 30
Plaid for fall isn't exactly groundbreaking. Clashing plaids for fall, however, feel fresh and new.
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Puff sleeves: check! Headscarf: check! Floral print: check! This look proves that one look really can have it all.
15 of 30
Cue the Crazy Town's "Butterfly."
16 of 30
This slideshow is a lesson on how to make sports bras a fashion staple in seven takes.
17 of 30
This handknit cardigan-and-denim midi skirt combo is a '70s dream I don't want to wake up from.
18 of 30
This look is about as soothing as a cup of warm oatmeal on the first chilly fall day.
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Take a seat — the master of fall dressing has arrived.
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Even better than matching your hair to your dress is coordinating your makeup.
21 of 30
Summer vacation isn't over until we say it is.
22 of 30
If this isn't the most perfect shade of orange, I don't know what is.
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It's called cottagecore, haven't you heard of it?
24 of 30
Who else is feeling the sudden urge to buy a leather blazer and patterned, '70s bell-bottoms after seeing this look?
25 of 30
Spotted: an orange Loewe elephant bag (and a pair of matching glove shoes).
26 of 30
Can we all agree that woven beach totes should be seasonless from now on?
27 of 30
The 2020 US Open started on Monday, which means it's time to pull out your best pleated tennis skirt.
28 of 30
When you have nowhere to go, there's no such thing as being overdressed. So, go ahead and wear your fanciest gown. What's stopping you?
29 of 30
Platform flip-flops, Bermuda shorts, and sparkly handbags — the '90s are back, and we're here for it 100%.
30 of 30
Tiny, sweater shorts are the ultimate summer-to-fall transition piece.
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