With summer well and truly behind us, t’s time to start thinking about the best autumn outfits. We drew inspiration from street style to make putting outfits together a little easier. Here, you’ll find plenty of transitional outfit ideas to carry you through those in-between summer-to-fall days. (Pro tip: Layering is key.)
Whether you’re wondering how to keep your favourite poplin skirt in rotation or increase the shelf life of your long-line denim shorts, these tips and tricks are just plain smart. Plus, you’ll see how to incorporate autumn’s biggest jacket trends (lots of suede and tailoring, for starters) and all those runway-ready shoes, such as riding boots and satin slippers, just in time for those first few leaves to fall. Ahead, the nine best autumn outfits to ensure you feel your very best all season.
Minimalism with a twist
Stick with the staples, but with stylish tweaks. Trade your trusty straight-leg jeans for a pair of bootcut denim, and wear them with a white T-shirt and collarless blazer – a standout jacket trend for autumn. Mesh flats and a work-ready tote bring a cool downtown attitude to this everyday outfit.
Mango tailored suit blazer
Agolde Kick bootcut jeans
Reformation Britt ballet flats
Suede simplicity
Upgrade your barn jacket to a suede version to face the cooler months. It will provide that extra dose of warmth you need on chilly days, plus it looks ultra-sleek when styled with a cardigan, wrap skirt, and walkable riding boots (one of this season’s biggest shoe trends). Don’t forget the suede handbag, either.
Nour Hammour barn suede jacket
Cos twist-detail midi skirt
The Row Nobilis riding boots
Tory Burch Romy suede hobo bag
Black-and-brown combos
Mixing black and brown is no longer a fashion faux pas; we actually encourage blending them together. To do it right, play with modern silhouettes and texture. Style a collarless jacket with a woven or pleated skirt and pair it with of-the-moment accessories like slingback pumps, a cord pendant necklace, and a suede handbag.
Jonathan Simkhai Marlowe jacket
Massimo Dutti long flowing pleated skirt
Now 46% Off
Toteme croc-embossed slingback pump
Heaven Mayhem Julia necklace
DeMellier London the New York shoulder bag
Transitioning shorts from summer to autumn
If the hot and cold days of autumn have you wondering what to wear, layering is the key. Long-line denim shorts are an unexpected saviour in transitional outfits. Wear them with your favourite oversized blazer, a trend-forward lace-trimmed top, and knee-high boots to perfect the look. Shed the layers as needed if and when that afternoon heat hits (fingers crossed).
Gap long-line denim shorts
Now 50% Off
Staud Wally leather knee boots
JW Pei Orla weave handbag
Mixing in menswear
Plaids, tweeds, checks—they’re everywhere. Nothing feels more quintessential than these prints at this time of year, and with pencil skirts being back in a big way, we recommend grabbing one in a traditional suiting fabric, like glen plaid or tweed, for a sharp, polished look. It looks so crisp when worn with a white button-up shirt, kitten-heeled pumps, and bold earrings.
Banana Republic white boxy cotton poplin shirt
Cos draped checked midi skirt
Jenny Bird Sundra earrings
Madewell Shopper tote bag
The statement coat
Update your outerwear game with one investment coat that can be worn over everything. A suede topper is a wise choice; it has a soft and luxurious look and feel for fall. As noted earlier, don’t be afraid to mix brown and black, and play with texture in your look, such as with faux leather trousers.
Massimo Dutti long suede trench coat
Now 45% Off
Theory wool crewneck sweater
Whistles black ultimate leather trousers
Now 25% Off
Aeyde Helia nappa leather black heels
Cos mini Studio bowling bag
Western chic
Lean into the western trend that we saw throughout the summer months into autumn. Style your favourite plaid shirt with a pair of chunky moto boots and a denim tote bag.
A.L.C. Hazel faux-fur jacket
Marant Etoile Yalisa plaid cotton flannel shirt
Levi’s high-rise slit skirt
Now 22% Off
Play with poplin
Your white poplin skirt doesn’t need to be tucked away, even when the temperatures turn. As seen here, you can extend its life through the season and style it with a long-sleeved turtleneck and peacoat. Add modern accessories, such as a very on-trend day heel and co-ordinating handbag, to keep the skirt in rotation well into the autumn.
& Other Stories navy pea coat
Commando Butter turtleneck
Aligne Natalie elasticated cotton midi skirt
Now 14% Off
Khaite Cecilia leather pumps
Freja New York mini Chrystie shoulder bag
Remixed basics
A trench coat, a button-up shirt, and jeans are the makings of a foolproof autumn outfit. However, with the help of a few stylish add-ons, you can make this combination even better. Add a pair of ballet flats in satin instead and a suede top-handle bag for more texture. It’s a classic and cool look without trying too hard.
Uniqlo relaxed trench coat
Rag & Bone Maxine button down shirt
Essentiel Antwerp cotton cropped barrel-leg jeans
Dolce & Gabbana My Sicily handbag
Now 24% Off
