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Fashion

End-of-Summer Outfits: Back to The City with Style

As summer fades, step back into the city beat with confidence. No matter what you’re dressing for, our guide to end-of-summer outfits will help you effortlessly transition your style.

As languid summer days carry on, it’s hard to imagine that colder weather is just ahead. Once vacations are over, we can’t help but long for a change from the lazy hazy rhythm of summertime. The good news is that you don’t have to wait for cooler temps to start transitioning your style for the fall; the change in setting as we get back into the groove of city life is enough to warrant a shift in how you dress. How do you know where to take your style in the time between seasons? It’s all about building the perfect end-of-summer outfit.

As you leave behind paradise and head back to everyday life, mix the best of both worlds to build the perfect dress code for the end of the season – back-to-the-city outfits that incorporate the relaxed air of a vacation look with cosmopolitan practicality. Striking a balance between comfort and style is the key to cute end-of-summer outfits. Let your bold colors and beachy prints melt into softer hues like the currently trending butter yellow perfect for a feminine office outfit. You can start to reintroduce color blocking when you get back on your block with timelessly chic, black-and-white looks. For busy days, sportswear in earth tones will bring the beauty of nature into your daily routine. Read on to uncover the best end-of-summer look that will help you take your style to the next level: the comfy-chic aesthetic, the endless summer vacation donning summer wears in the city, denim-centric street style, and sporty clothes for those of you aiming to get back in the workout swing.

Back to The City: Comfy-Chic Looks

This season is all about the comfy-chic look which can easily be adapted for the end of summer. This fall’s fashion trends take professional, workwear-inspired ensembles out of the boardroom and into the world, adapting them for any setting. This approach allows for both elegant and practical outfits for everyday life. When your schedule is full of meetings, errands, and the general hustle and bustle of the city, the comfy-chic aesthetic allows you to feel comfortable and well-dressed. How to build your outfit? Start from the ground up with a pair of low-top sneakers that can add a pop of color or render a workwear look a little more laid back, otherwise, you can go for a more feminine appeal with a pair of trendy ballerina-inspired shoes or timeless Mary Janes. A pair of wide-leg pants, like Palazzo trousers, provide comfort and give dimension to your silhouette.

Continue the comfort with an oversized button-up or flatter your figure with a bohemian-style blouse that has the same free-spirited nature as your favorite summer cover-up. A maxi dress can act as a one-stop shop for a cute end-of-summer outfit, but be sure not to select too heavy of a fabric. Complete the look by tying an oversized sweater around your neck or waist, or drape a cardigan over your shoulders and accessorize with a bag, like the trending Bauletto handbag, that is comfortable to carry and has space for all of your daily essentials like sunscreen (because protecting our skin is important all year long), hair clips, laptop, wallet, and more.

Model wears black top and maxi skirt with a focus on Lie Studio cuff bracelets and Proenza Schouler leather Mary Jane flats

Summer Clothes: How to Wear Them in The City

Before you put them away, try styling your favorite summer pieces for the transition to fall. Ideal for showing off your tan once you get back to the city, your summer sundresses can be styled for the concrete jungle. That long white dress that you styled for vacation? Make it office-ready by swapping out the raffia bag and sandals for a show-stopping shoulder bag–might we suggest Gucci–and a pair of sneakers, like the Adidas Gazelles. For a night out or a dinner date, wear a little black dress with a blazer draped over the shoulders and a slingback heel. As the weather gets cooler and your boots come out of storage, pair them with a flowy midi dress and tote bag for the perfect end-of-summer weekend look. Don’t be afraid to continue wearing your linen pants, like the iconic pairs from Cucinelli, well into September. Wear them with a t-shirt of the same color for a trendy monochromatic look–and don’t forget the sunglasses.

Model poses on a stool barefoot with hair in an updo. Wearing Tove silk satin long dress with Jil Sander small hoop earrings

Metropolitan Street Style: Denim That Conquers All

Summer is just long enough that by the time August rolls around we have started to miss our jeans. Luckily what is perhaps the most iconic streetwear look of all time focuses on our beloved staple. The combination of a t-shirt and denim has been the unofficial uniform of city dwellers for decades, and for good reason. An outfit composed of jeans that fit well and a comfy cotton tee can be elevated and adapted for just about any body type, personality, or setting. This fall, the denim trend that has captured everyone from celebrities to CEOs, is comfortable and figure-flattering wide-leg jeans with an aesthetic nod to the 80s and 90s. We have plenty of amazing options from RE/DONE, Mother, Bottega Veneta, and more.

On top, keep it simple with a black or white crew neck tee or, in higher temps, a ribbed cotton tank. For those who left their heart at the beach, we suggest adding a bohemian-style belt or a pair of flat leather sandals. This fall, jeans can be substituted for a fashionable well-structured denim skirt. Be it a pair of jeans or a skirt, denim is in good company with a lightweight jersey top, crisp poplin button-down shirt, or a wool crewneck sweater–to be draped over the shoulders until fall is in full swing. To make your entire outfit a stand-out look, try finishing it off with a cuff bracelet, chunky earrings, or a statement necklace. Depending on where you’re off to, you can select a more formal shoe like slingbacks and pumps, or stay spry in a pair of sneakers.

Model wears Carhartt WIP overalls, Adidas Original top, Jacquemus jacket, and Adidas sneakers. Accessorized with Max Mara beanie & Rabanne sequined bag

Office Outfits: Go Back to Work in Style

Returning to work after the summer holidays can be difficult, which is why the transition should be gradual, thus applies to your personal style and outfits as well. A new pair of shoes can get you excited to head back into the office and will inject some sense of newness into your staple workwear looks. This season’s must-have shoes are suede moccasins and décolleté heels. With these two shoe styles, there’s something for everyone. Explore different colors and details to find a loafer-style shoe that suits your style and heels in varying heights. Maintain summertime comfort levels with soft tailored suits which are the height of class but also extremely comfortable. Add dimension through layers with a supple silk blouse.

We recommend sticking to a classic and refined color palette of black, grey, navy blue, and beige for business environments. It’s important to find breathable fabrics for your work wardrobe at this time of year, including lots of cotton, lightweight wool, and linen. Gear up for the cold temps and start thinking about a long coat to be shown off on your commute and meetings over hot coffee. This year’s must-have pieces is a structured, long-length coat that makes for a great investment because of its cost-per-wear rate – think Burberry trench or wool overcoat. You can wear a long coat with just about anything underneath–sheath dresses, midi skirts and tights, cardigans and trousers, and more. For an off-duty look, sporty pants, a crossbody bag, and a contrasting scarf are ideal.

Model wears white wool suit from brand TOVE with Bally loafers, Simuero hoop earrings, and Isabel Marant suede clutch

 Getting in Shape with Sportswear Looks

After the leisurely summer period in which routine and healthy habits go by the wayside in favor of rest and relaxation, we return to the routine of daily life and pick back up our workout regime. Sometimes this takes a little push of encouragement from a new purchase. A fun and funky water bottle from 24 bottles? A new set to wear to the gym? You can get inspired by our selection of sports accessories that include ergonomic yoga mats, hand weights, baseball caps, and more. Our activewear selection has some of the most fashion-forward looks in breathable, quick-drying materials. Sportswear clothing is perfect for busy city days when you have to be everywhere from the gym to the supermarket to lunch with friends.

A Tory Sport tennis dress can keep you looking fresh and stylish while running errands, and don’t forget a cardigan on chillier autumn days. Another great transitional outfit with its roots in sportswear is a trendy tennis shoe with leggings, a graphic tee, and a blazer. Crossbody or tote bags pair nicely with sportswear looks, and you can even match the color of your bag to your gym shoes. This fall’s sportswear trends focus on colors inspired by nature. Let your days be colored by the introspective and soothing tones of the world around the city with stonewashed blues, forest greens, burnt siennas, and more. Let our collection inspire you to develop your end-of-summer looks by finding pieces to help you make the transition from summer to fall.

Model in sportswear look: Adidas crop t-shirt & Brunello Cucinelli tie over Dsquared2 striped polo, Adidas sweatpants, and sneakers

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