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From Summer to a Summer-Like Fall

It’s again time to say so long to summer and turn toward fall, knowing full well we’ll still have some scorching days in the forecast as we all yearn for a crisp autumn breeze.

Figuring out what to wear as one season transitions to the next is always challenging, but the turnover from summer to fall feels even more frustrating because everyone is so ready for chunky knits and boots and denim layers, but it’s just too darn hot out to fully dive into fall fashion.

Here are a few tips, tricks, some savior pieces, and outfitting ideas as we end summer but are still blazing in a summer-like fall.

First up, Bermuda shorts. The styling possibilities with a longer short make them an ideal garment for this time of year. You can go with a tank top and sneakers for a casual look when the highs are in the 80s. For days when the wind picks up and the feelings of fall are just at your fingertips, style them with a button-down cardigan combo and kitten heel. Lands’ End has a Women’s Classic 12” Chino Short in Navy, Chambray, or Light Stone. I’d wear the chambray in a more casual setting and save the navy for work. There’s also Gap Factory’s 9” Downtown Bermuda Short in Black and Khaki, which again can be worn with a tee-shirt and flip flops, just as easily with a blouse and ballet flats. Hot tip! When dressing up a pair of shorts, be sure to add a belt to define your overall silhouette and add some polish to your look.

If you’re ready to move away from shorts entirely this season, then consider barrel bottoms. This silhouette offers a fresh take on the straight and skinny leg pant, combining the laid-back vibes of summer with the coverage and practicality of fall. Old Navy’s High-Waisted Pull-On Barrel Jeans pair well with a fitted tee and Birkenstock-style sandals for the weekend. A definite outfitting option for any upcoming farm or foliage-related fall activities. Uniqlo’s Jersey Barrel Pant has more of a 9-to-5 style with a matching sweater set and belted. If you find the volume of this pant style intimidating, start with a smaller, less wide barrel leg.

Another “style hack” for this transitional season is switching out your summer white pieces for summer black versions. A black summer dress, such as WAYF’s Smocked Fit & Flare Sundress from Nordstrom Rack, makes for an easy outfit pre- and post-Labor Day. Wear it now with a thong sandal and woven bag, then ease into an autumn look with a denim jacket and cowboy boots as the temps start dropping. You can also swap your white poplin skirt for a black version like Loft’s Poplin Pleated Maxi Pocket Skirt. Pair it with a peasant blouse during these last days of summer, then, as the air slowly starts to crisp, wear this skirt with a turtleneck and blazer for an autumnal business casual outfit. If you’re not ready to let go of your summery white clothes just yet, style them with black accessories, such as shoes, belts, and bags, as a nod to the changing season.

Last fall, I finally embraced the rugby stripe trend with a sweater from Anthropologie, wearing it with cropped trousers and loafers. Rugby-inspired pieces speak to the back-to-school theme of this particular time of year and can serve you well into autumn, winter, and spring, depending on the stripe colors. For now, go for earth tones with bright contrasts, like J.Crew Factory’s Striped Rugby Shirt in a camel and red. Wear it with your Bermuda shorts to double down on your transitional look. As the holidays roll around, pair this knit with a brown corduroy skirt, tights, and boots. And since it’s (at the time of this writing) 39% off, pick up the same shirt in navy and stone for a casual spring look with jeans and a puffy vest. Another great source for rugby stripes is the men’s section, particularly in your local thrift store. An oversized shirt lends itself to a more casual look, so be sure to balance out the volume up top with a fitted bottom, like a skinny crop trouser or leggings.

Another styling trick to incorporate into your transitional season dressings are T-shirt dresses. From maxis to minis, these easy-to-throw-on garments can be dressed down or up and layered for these in-between times over the next month. Natural Life’s All Day Cotton Tee Dress in Black or Teal, with its twisted neckline and elbow-length sleeves, makes for a simple yet chic piece for cooler mornings and sunny afternoons. It’s especially versatile when layered with a striped V-neck sweater that can be thrown over the shoulders as the day warms up. If you’re looking for some patterns, check out the same brand’s Frankie Knit Cotton Tee Midi Dress in floral color ways of turquoise, pink, or cream. These tones and the delicate print give an expected moody vibe that fits into the darker romance that autumn brings. I see these working well into the season with cowboy boots and shackets, while now, pair with a chambray shirt and sneakers.

Speaking of sneakers, for my money, they are hands down the ultimate shoe for transitioning from summer to fall. I’m not talking about your ratty wear-without-socks yardwork or gym sneakers. But a sleek, clean, possibly slip-on version that provides function and comfort. Dr. Scholl’s Time Off Platform Sneaker fits the bill as they are actively supportive, while also being minimalistic to wear with jean shorts or with wide-leg trousers. However, if you want to go bolder with your seasonal transition style, check out Dolce Vita’s Notice Stitch Sneakers in various leopard prints. With a removable insole, these also support the foot while bringing a pop of print to your midi black dress or barrel pant and button-down.

With Labor Day in the rearview and eyes turning toward a bustling autumn, the weather may still feel summery, so until we get into the true fall forecast, hopefully, some of these outfitting ideas and pieces will see you well into sweater weather.