5 Effortless Outfit Ideas We'll Be Relying On Throughout September
From summer dresses paired with thicker wool blazers to poplin skirts worn with leather bomber jackets, here's what to wear in September. Scroll for editor-approved outfits.


Brittany Davy
No matter how long ago you left school, September brings with it that feeling of starting afresh. It's a good time to edit and fill in wardrobe gaps—perhaps a leather blazer or an Instagram-worthy handbag? Though we're not ready for a complete seasonal switch just yet (we're officially in that weird end-of-summer period), you can still wear your summer investments whilst introducing new autumn pieces too. I've scoured the latest outfits of some of our favourite dressers to bring you a little inspiration for what to wear this month. Keep scrolling for chic September 'fits to copy…
What to Wear in September
1. Leather Blazer + Tailored Trousers + Monochrome Accessories
Style Notes: Leather tailoring is stealing the show left, right and centre this autumn, and here's a case of styling a cool jacket with classt wide-leg trousers, and tonal accessories. It's an age-old formula, but if it ain't broke, why fix it?
Shop the Look:
These are a bestseller for good reason.
2. Bomber Jacket + Polo Sweatshirt + White Skirt
Style Notes: In case you hadn't noticed, white skirts were a winner yet again this summer, but to make them more autumn-appropriate, add a sweatshirt and leather bomber jacket.
Shop the Look:
3. Button-Down Shirt + Jeans + Mules
Style Notes: A button-down shirt is a winner no matter the time of year, and as Marilyn shows above, even your lightweight iterations can be repurposed for cooler weather with some clever styling. Simply swap out your linen trousers for some dark wash denim.
Shop the Look:
4. Wool Blazer + Midi Dress +
Style Notes: I'm very much in autumn mode, but even I'm not ready to say goodbye to my white summer dresses quite yet. To make them work for the colder weather, add a boxy wool blazer that will not only look incredibly chic, but keep you warm and cosy as well.
Shop the Look:
5. Long-Sleeve Top + Track Pants + Slingbacks
Style Notes: Is there a way to make comfy track pants look chic? Of course you can! The art lies in juxtaposing the baggier silhouette with sleek slingback heels and a fitted top. See Sabina's above outfit for all the styling inspo you could need.
Shop the Look:

Remy Farrell is a London-based fashion editor with 10 years of experience covering fashion, beauty and lifestyle. After graduating with a journalism degree and working on the fashion teams for titles such as Grazia, Elle, and British Vogue, she moved into the luxury e-commerce sector, working as fashion assistant at TheOutnet.com After expanding an assisting and styling portfolio that includes talent such as Gigi Hadid, Victoria Beckham and Miquita Oliver, she ventured into beauty, compiling reviews and diverse beauty content.
In her role as fashion editor at Who What Wear, Remy is interested in discovering new brands to share with the WWW UK readership, and loves uncovering hidden gems to make shopping accessible to everyone.
- Brittany DavyEditorial Assistant
-
How Métier Founder Melissa Morris Created an A-List–Approved Luxury Bag Brand
The secret? Intentional design, quality materials, and a timeless aesthetic.
-
I’m a Senior Shopping Editor—These Elevated Yet Affordable Nordstrom and Old Navy Fall Picks Have My Attention
Just about everything is under $100.
-
These Easy Outfit Formulas Make Even Fall's Most Polarizing Boot Trend Look Cool
See the inspiration inside.
-
Click Here for Proof That This Sophisticated Shoe Color Works With Both Jeans and Dresses
Versatile and chic.
-
How I Let My Many Personalities Flourish This Fashion Month
Here's everything I wore, from New York to Paris.
-
If You're Tired of Predictable Fall Outfits, Try This Styling Trick Instead
Bold and anything but basic.
-
I Live in NYC—These Are the 5 Essential Pieces I Rely On Every Fall
My favorite.
-
6 Fall Outfit Formulas I'm Stealing From Zoë Kravitz
Effortless, polished, and sophisticated.
-
5 Street Style Trends From Milan Fashion Week That Will Be Everywhere This Fall
Take notes.
-
Everyone With Good Taste Is Styling Jeans With This Specific Jacket Style Right Now
You probably already own it.