I might be a fashion editor, but I'm also only human. So, I’m not afraid to admit that sometimes I struggle with dressing while we transition through the seasons. After all, I live in New York City, where during the month of September, it can range from 26 degrees and sunny to 15 degrees and rainy, which doesn’t exactly make getting dressed easy. It's a constant guessing game—do I stuff an extra layer into my tote bag? Or do I stick to breezy cotton pieces to avoid breaking out in a sweat?
This challenge becomes even more pronounced when it comes to dressing for the office, where you want to look put together and polished but still comfortable. If you can be ready to leave in under 10 minutes—even better. I'm also not a morning person.
As autumn is fast approaching, I decided to scroll through my Instagram feed and hunt for chic summer-to-autumn transitional outfits that are low-effort but still polished enough to wear to work. Think smart tailoring, sharp accessories and quietly luxurious colour palettes. I ended up with a handful of seriously stylish looks that check all of my boxes, and which I plan on recreating while we transition into the coming season.
Keep scrolling to see the six summer-to-autumn office outfits that I haven't stopped thinking about.
1. Black Midi Dress + Flat Shoes
Style Notes: A good black midi dress is the backbone of my office wardrobe. It's seasonless, dressy enough, and such an easy piece to style. For transition from summer to autumn, I'm styling mine just like Elsa Hosk did above. With the perfect pair of flats, plus a tote bag since I'm heading into work.
Shop the Look:
I wear my Le Specs year-round.
A dainty addition to any look.
COS is my go-to for affordable dresses that feel luxurious.
This heel feels low enough for all-day wear.
Roomy enough for everything you need—and then some.
2. Boat Neck Tank + Leather Belt + Jeans + Ballet Flats
Style Notes: I wore this outfit on my last day at the office. It's the perfect simple, easy, yet stylish outfit to wear to work in between seasons. If your office gets cold (like ours does) feel free to throw a good cardigan in your work bag.
Shop the Look:
A basic with a twist.
It's all about the details.
I always think dark-wash denim feels more formal—and more autumnal.
A reliable watch is a 9-5 essential.
3. Sleeveless Turtle neck + Jeans + Heels
Style Notes: It doesn't get more summer-to-autumn appropriate than pairing a knit sweater with an open-toed shoe. This outfit is admittedly quite simple, but with the right styling, it feels very modern and chic. I'll definitely be recreating this one come September.
Shop the Look:
The ultimate layering piece.
Often the simplest pieces are the most impactful.
I love the wash of this pair.
So many editors I know swear by Demellier for long-lasting work bags.
You can still get away with strappy sandals for the time being.
4. Button Down + Bermuda Shorts + Pumps
Style Notes: Now this outfit, I love. The satin button-down feels relaxed yet still formal enough to wear to work and the bermuda shorts are undeniably fashion-forward. The pumps add an extra something special, too.
Shop the Look:
Simple but oh-so classy.
The only shirt brand you need to know.
Beautifully tailored—I'd expect nothing less from The Frankie Shop.
Suede accessories are one of the first signs of autumn.
I always recommend these affordable slingbacks.
5. T-shirt + Trousers + Sandal + Leather Belt
Style Notes: This outfit is compiled of all of the basics you already own and adore. A great T-shirt and trousers outfit should not be underestimated, especially paired with the right belt and shoes. I'm certain I'll be copying this outfit for work ASAP.
Shop the Look:
A stylish change from your plain gold hoops.
The relaxed fit will bring a sense of ease to your work wardrobe.
Expect compliments from all of your colleagues.
Trust me, you'll reach for these almost daily.
These sandals have entered icon territory.
I've had my eye on this bag since last year.
6. Jersey T-Shirt + Maxi Skirt + Shoulder Bag
Style Notes: This look combines sporty elegance with office-ready style. Pair a jersey T-shirt with a matching jersey skirt for a cohesive, monochromatic outfit. Elevate it with a structured shoulder bag in a contrasting colour or texture for added sophistication. Complete the look with minimal jewellery and sleek loafers for a polished finish or, if you're after maternity fashion like Monikh, nothing says comfort quite like thong sandals.
Shop the Look:
Depending on your dress code, this casual staple can easily be dressed up.
That's right, linen can work for autumn, too.
This colour is divine.
An elevated take on the flip-flop.
This story was published at an earlier time and has since been updated.
-
I’m Already in Autumn Mode: 7 Elegant Outfit Ideas I’ve Just Added to My Mood BoardI'm counting down the days.
-
Basic Jeans Aren't Out, But This Denim Trend Feels Way More 2025Hint: it's not blue, black or white.
-
8 Autumn 2025 Trends That Are Already It-Girl ApprovedNew season loading.
-
Still Over Skinny Jeans? This Elegant Denim Trend Is Making a Major Comeback for AutumnGet ready.
-
Hold the Basic Jeans—This "Dated" Denim Trend Is on Its Way BackGet ready for this comeback.
-
It's Already Autumn at H&M—Chic, Organised People Will Snap Up These 9 Buys Before AugustI'm in autumn-mode already.
-
As Seen in Paris: The Two Colour Trends Everyone Will Wear Together This AutumnDua Lipa approves.
-
I've Mastered the Art of Chic Office Dressing—These Are the Pieces That I Always Rely OnYour 9 a.m. meeting is about to get a lot more stylish.
