Just like that, we’re heading into fall and I couldn’t be more excited to step into a brand new season. For me, it marks a new time to try out some trends I spotted on the F/W 20 runways and that I finally have an excuse to start wearing boots again (yes, they’re my favorite shoe style). Having attended fashion week in Milan for the first time last season, I’m particularly excited about what I saw firsthand from the shows there, so it should come as no surprise that a few of the earliest fall trends I’m adding to my wardrobe are rubber boots inspired by the looks at Bottega Veneta or polished bags as spotted at Gucci.
It's not limited to those, though, and there are plenty more early fall trends I’m already trying out. Here, get a look at the transitional outfits I’m wearing now as we head into the new season and ideas for how to style them in the coming months.
Leather Bermuda Shorts
Leather Bermuda shorts are one of my favorite transitional pieces to wear at the moment, but also in the months ahead. Right now, I love the idea of styling them with an oversize button-down and puffy heels. Once fall arrives, I'll be swapping in ribbed knit sweaters and tall thigh-high boots to tuck underneath the shorts.
This pair is actually one I ordered at the beginning of the year but the trend is gaining even more momentum, so they're definitely a smart, versatile buy for fall. I love that they instantly read as polished but are also super comfortable and easy to style in a number of ways. Look for shorts that are loose but tailored and cut in a long length. I'm especially gravitating toward rich, versatile neutrals like camel, butter yellow, and black.
Shop leather Bermuda shorts:
Spotted in the F/W 20 collections of designers like Bottega Veneta, Prada, and Versace, rubber boots were one of the most surprising trends designers put on the runways. But, as practical fashion is winning out as we head into fall, it's no surprise that the Wellington boot trend is already picking up steam.
Right now, I've been pairing classic Hunter boots with cutout slip dresses and breezy, cottagecore pieces that act as the perfect counterpoint to the traditional countryside shoe. As we move into fall, I'll be taking some inspiration from the runways and wearing them with long dresses or leather skirts.
Shop rubber boots:
Spending more time at home, my contacts have been getting a break and glasses have become my most essential at-home office accessory. Ready for an upgrade to some old plastic frames that feel dated, I was eager to update mine to a more fashion-forward pair. Since glasses are such a personal buy that often comes down to face shape, I was hesitant to take my chances on a style I hadn't tried out in person.
That's when I learned that Chanel recently launched eyeglasses on its site, designing a process that mimics an in-store experience as much as possible with recommended local opticians and virtual try-ons that allow you to test out their 300 styles straight from your phone.
When virtually testing out frames, I instantly spotted Chanel's oversize aviator-style glasses and knew they were perfect. It's a trend that has been spotted in the collections of every major designer including Bottega Veneta and Gucci recently, but they actually remind me of a pair my dad wore in the '80s, which is what really won me over.
Shop pilot glasses:
While tailoring isn't going away, we'll be seeing more relaxed silhouettes pop up for fall. I'm all about the looser, comfier takes on trousers that are replacing more fitted styles, and recently, relaxed trousers have become one of my most essential wardrobe staples. I love that they immediately make me feel pulled together but still comfortable.
Last month, I was wearing loose trousers with a tube top and flats, but heading into fall I've swapped in color-block boots and a structured, padded T-shirt. These pants from London-based brand Tove have been on my radar for months and I can confirm that they're just as stylish as they are cozy. In the coming months, I'll be tucking them into knee-high boots.
Shop relaxed trousers:
If the recent runways are any indication, vintage-inspired bags are making a major comeback. In the Prada S/S 21 menswear collection, models clutched sleek, minimal leather bags that are a throwback to the brand's popular styles from the '90s. Though these won't be released for a while, we can be confident it's a trend that will continue long into next year.
So where are they popping up this season? Gucci for one. One of the defining bags this season will be its Jackie 1961 hobo bag—a style originally named after Jackie O when it was first created five decades ago. And now, it's been reimagined with fresh colors like butter yellow and turquoise, as well as a new shrunken shape that taps into the mini bag trend that has been popularized in recent seasons.
To play down the sophistication of the bag, I paired it with a boilersuit and my favorite vintage kitten heels. I also imagine wearing the bag with the same shoes and a pretty powder-hued coat in the coming months. This is an investment buy that you can really count on having forever. (After all, it's been cool for almost 50 years.)
Vintage fashion is one of the things that inspires me most.
Shop polished bags:
If you've been reading some of my recent stories, you probably know that I won't stop talking about ribbed knits. To be honest, I'm not a huge sweater person, but I feel like these pieces are a cool, refined take on knitwear that I can get behind. The elevated basics are a great new-season take on basics that are endlessly versatile.
For my first foray into ribbed knits, I was drawn to this beautiful (and under-$100) strapless bustier top. Here, I'm wearing it with belted trousers and gold jewelry (to me, the perfect outfit transitional outfit to wear right now). For later this season, I would wear it tucked under a matching skirt suit with chunky Chelsea boots, or with Bermuda shorts and second-skin thigh-high boots. I'm already excited to try that last outfit idea once I order some form-fitting OTK boots.
Shop ribbed knits:
While I've definitely been leaning into looser silhouettes when it comes to suiting, I couldn't ignore the cropped blazers that were all over the F/W 20 runways at shows including Christopher John Rogers, Jacquemus, and Eckhaus Latta. Part of a larger trend of reinvented suiting, these new takes on classic blazers are about to be everywhere.
With sustainability in mind, I've been shopping for more vintage pieces recently, so hunted down an '80s (I'm guessing) Dior cropped blazer to try out the trend for myself. Paired with wide-cut jeans (the only denim silhouette I want to wear right now) and my favorite slingbacks, this is my ultimate outfit formula for an easy WFH look.
Shop cropped blazers:
Speaking of suiting, here's another version I'm obsessed with. I like to call these "back to basics" suit sets, as spotted in the F/W 20 collections of brands like Bevza, Olivia Theyskens, and Givenchy. While I clearly love the reinvented takes on suiting like the cropped blazers above, there is simply nothing as timeless or classic as a great tailored set.
For the new season, wearing these in a fresh way really comes down to the styling. On the runways, we saw jacket sleeves tucked into leather gloves, with turtleneck and sleek boots, blazers with nothing beneath, and sets worn with bra tops layered under them. Here, I took on the bra top version but I'm looking forward to finding fresh ways to wear this blazer set as the season continues.
Shop suit sets:
Shop the matching Wide-Cut Pants ($50).
Shop the matching Elvira pants ($234).
Shop the matching Pleated Pants ($80).
Kristen Nichols is the Associate Director, Special Projects at Who What Wear with over a decade of experience in fashion, editorial, and publishing. She oversees luxury content and wedding features, and covers fashion within the luxury market, runway reporting, shopping features, trends, and interviews with leading industry experts. She also contributes to podcast recordings, social media, and branded content initiatives. Kristen has worked with brands including Prada, Chanel, MyTheresa, and Luisa Via Roma, and rising designers such as Refine and Tove, and her style has been featured in publications including Vogue.com, Vogue France, WWD, and the CFDA. Before Who What Wear, Kristen began her career at Rodarte, where she worked on assistant styling, photo shoots, and runway shows, and at Allure, where she moved into print and digital editorial. She graduated from the University of Southern California, where she studied art history and business, and currently lives in New York.
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