September is here and with it comes what I would argue is one of the trickiest months to get dressed for. The calendar says Fall! The weather often says absolutely not!
As soon as I am back from Italy I know I will personally be very ready for sweaters, suede, loafers, boots and all the delicious textures and hues that come with Fall dressing, but September requires a bit more restraint. (That won’t stop me from switching over my closet though…one of my least favorite activities and yet an inevitable form of seasonal torture 2x per year with my NYC closet situation).
All that being said, September’s edit of outfits are much more focused on transitional dressing rather than full on Fall since it’s currently 80° in NYC and plenty of other places. 🙃
(Don’t miss the August installment, especially if you have any final warm-weather trips on the the horizon!)
And because September also marks the unofficial beginning of Fall shopping season, I’ve updated my discount codes with the latest offers from many of the brands I regularly shop and share. Definitely worth a peek before you place any Fall orders!
Jenni Kayne: MEGHANDONO10
Freda Salvador: WITWHIMSY10 for first orders
M.M. LaFleur: WIT&WHIMSY20 for first orders
La Ligne: MEGHAND10 for first orders
Aurate: MEGHAND20
Sarah Flint: SF-MEGHAND15 for first orders
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Sweater + shorts weather is one of those magical little windows I wish lasted longer! I love the juxtaposition of a cozy oversized knit with bare legs and woven flats — especially in this tonal palette that feels Fall without being too heavy handed. For extremely warm days, just throw the sweater over your shoulders.
Also, I’m in love with Crown Affair’s hair products including these cute hair clips I’ve been using non-stop of late. Use code WITWHIMSY15 for 15% off!
Don’t miss: My Full Crown Affair Review.
This is essentially my Fall travel uniform: extremely comfortable pants that still look polished and a striped sweater from one of my favorite brands.
If you’re curious about La Ligne sweaters, I wrote all about them here (the review is freshly updated with the latest styles I’ve acquired!) but tldr worth every penny in my book. Use code MEGHAND10 for 10% off your first order!
My WFH outfits need to be comfortable, but I’m also infinitely more productive when I’m at least somewhat dressed for the day. Easy pants, an oversized tee, and a sweater to throw on when the AC gets cranking = ideal.
As a side note, these pants are perfect for traveling in. I wasn’t sure if the barrel leg look worked for me, but I’m happy to stand corrected! I recommend sizing up. I own the size 8.
I love how much more seasonal a simple striped shirt feels when you swap out denim for cotton poplin chocolate brown pants. Add woven flats while it’s still warm enough to wear them and this is exactly the kind of easy weekend outfit I want this month.
I love the idea of taking easy, relaxed separates and making them cocktail-ready with the right accessories and fabrics. A little sparkle + a great bag make silk taffeta pants feel appropriately elevated for a post-work drink. I know everyone talks about the Donni pants and while they’re fab, this pair from Reformation are a bit more budget friendly. I saw a girl wearing them in the chartreuse color on a recent trip and they looked so chic!
When it comes to sparkle Ring Concierge and Dorsey are my go-tos.
Don’t miss: My Dorsey Jewelry Review.
Can you tell I’m really leaning into brown for Fall? 😂 This is exactly how I want to wear it in September: with jeans, sneakers (under $150!) and a barn jacket you can add or remove depending on whatever the weather decides to do that day.
Also this brand has such a good selection of affordable bags, highly recommend perusing their site.
September is still a little too early for a full lounge set for grabbing coffee, so I like the option to wear shorts! Varley has a great collection of loungewear pieces you can mix and match.
Use my code MEGHAND20 for 20% off these everyday hoops.
Don’t miss: Athleisure Capsule Wardrobe
Personally, I am VERY ready for tall boots season but pairing them with a slinky dress is one of my favorite ways to start wearing them before it’s actually chilly out. And this green + suede + tortoise combination!? So, so good.
For cooler days, I’m a fan of throwing a sweater over my shoulders for a little added coverage. The La Ligne Ben Sweater is the perfect lightweight sweater for this. I also love this cardigan!
Don’t miss: The Best Sweaters for Spring and Summer.
This striped polo sweater immediately caught my eye — the brown! The navy! The cream! It feels like such a good September piece you can wear all through winter, too. Pairing it with cream denim and suede accessories lets you indulge in Fall dressing while still keeping everything lightweight enough for a warmer day.
I’ve been reaching for this lip balm constantly lately!
I love when a work dress does all the work for you and this one feels particularly special with its contrast trim and gold button detailing (and it’s from one of my favorite British retailers!)
And if you’re on the hunt for a new work tote this Fall, head to Cuyana. This bag is another style I’ve owned for many years and I like the versatility of the dual strap lengths.
Shop more Early Fall Favorites over in The Shop on w&w. It just launched for the new season 🎉
I hope you guys enjoyed this installment of monthly outfit inspo! Let me know if you end up getting anything from the edit - I’m always keen to hear your feedback!
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Hi Meghan! I tried your Jenni Kayne discount code but it didn’t work. Is it only for new customers maybe?