Buying Guide – Robb Report

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The sun is setting sooner, the temperatures are starting to dip, and a brisk air is slowly entering the atmosphere. This means that the dog days of summer are coming to an end—thankfully. Fall is just around the corner. The season of layering is almost upon us, and we need to dress the part. We need to put our best foot forward for the months ahead. 

This wardrobe change, of course, starts with our shoes. It’s time to start thinking about replacing our espadrilles, sandals, and other summer styles with options befitting cool environments and situations. This could be strolling in a park, basking in the ambiance of leaves turning red and golden yellow; cruising down an open road in a convertible, feeling the fresh air; heading to a gallery party, ready to mix and mingle with a fashion-forward crowd; or just taking our daily commute to the office. Indeed, there are footwear styles ideal for each scenario. Some are even so versatile that they’ll work for every and any activity we have on our dockets. 

Here to help spruce up our shoe racks is FARFETCH, the luxury platform that merges over 700 boutiques from 50-plus countries into one global marketplace. The assortment is vast and diverse: The site really does have every style available, from the chicest loafers to the sleekest boots. But we narrowed the list to five essentials, icons in the menswear space, designs that will stand the test of time and last for many autumns to come. 

Best Driving Shoe for Fall

Picture this: You’re driving on a deserted highway—perhaps overlooking the seaside at the Amalfi Coast or Big Sur—in your shiny convertible, top down, the sun shining and the cool autumn air hitting your skin. Your fit needs to match the vibe, and it starts from the ground up with a sleek pair of driving loafers from Tod’s. Indeed, the Italian label is synonymous with the style, engineering a piece of footwear that’s ideal for cruising. Called the Gommino, the sole of the shoe is covered with small rubber pebbles, a design that’s intended to relieve pressure when putting the pedal to the metal. Outside a vehicle, the Gommino instantly imparts distinction, perfect for taking leisurely strolls in a piazza or sipping on an espresso at your local café. It comes in a variety of materials and colors, but if you’re looking for the utmost versatility, this sweet beige option will work with every ensemble in your fall wardrobe.

Buy Now: $595

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Best Loafers for Fall

Another Italian footwear icon is Gucci’s horsebit loafer, a shoe inspired by the equestrian lifestyle, marked by a distinct metal detail on the throat. There are now endless iterations of the style, but the Jordaan is the OG, a shoe that has cemented its standing in the annals of fashion history, worn by too many style icons to list. Its reputation and longevity in the menswear space are a direct result of its unwavering design; the perfect-size heel and sleek contours, punctuated by the lustrous horsebit, continues to dominate. The Jordaan just works, no matter the occasion. It can be worn with jeans and a bomber or paired with a spiffy two-piece suit under a sharp Chesterfield coat. It can be worn with socks or without them. It really surpasses all style boundaries—especially in this classic black colorway. 

Buy Now: $920

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Best Ankle Boots for Fall

Of all the footwear styles available, the one most indicative of the fall season is the trusty ankle boot. From the length of the shaft to the durable closed toe, the design is simply ideal for the rain, wind, and the overall chill. Most importantly, it’s much sleeker and more versatile than other boot options: It can easily be dressed up or down, depending on what you have on your docket. When the environment is too cold and damp for loafers or when an event is too formal for sneakers, ankle boots are the safest bet. And if you’re in the market for the best pair among the many, many options available, look no further than the Elias from Jimmy Choo. With its square toe, streamlined contours, elegant zipper, and just the right amount of lift, the Elias absolutely exemplifies the phrase “well heeled.”

Buy Now: $1,295

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Best Sneakers for Fall

In the avenues of SoHo, the streets of Belleville, the open spaces of Deptford, or in any fashion-forward neighborhood across the globe, it’s evident that the footwear of choice is sneakers. Not just any sneakers, though, but grails, the kinds of styles that hypebeasts wait on blockbuster lines to attain, the kinds of styles with oomph. Understanding this more than most is Off-White, a leader in luxury streetwear, a brand that takes classics and elevates them. Case in point: this eye-catching update of Nike’s celebrated Air Max, festooned with exaggerated stitching, taped seams, and bright orange detailing. It’s a sneaker that drips swagger. Note: There are only limited quantities available, so it’s best to score them while they’re still up for grabs. 

Buy Now: From $555

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Best Combat Boots

When it comes to heavy-duty footwear, something that will really combat the elements, nothing beats, well, combat boots. It’s all there in the name. The style is distinguished for its sturdy lace-up closure, lugged sole, and tough leather exterior—characteristics that have made it the go-to style for punk icons, bikers, rockers, and those that smell like teen spirit. Indeed, combat boots have an air of rebellion about them, historically worn with leather jackets, deconstructed denim, or flannel. Lately, however, combat boots have become mainstream. As seen on many catwalks across the fashion capitals, brands are pairing the shoes with suits and refined daywear. And one shining example is Balenciaga, a label that pushes the boundaries of fashion, offering pieces with an unmissable edge—a sentiment that’s reflected in this pair. It features all the trappings of the OG but packs more of a punch with its worn-effect exterior. What’s more: It’s made under the guidance of Good On You (an agency that rates the sustainability of brands). Which means you can feel just as good as you look. 

Buy Now: $1,200

Shop Balenciaga

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