Step confidently into fall in tall boots, midi skirts, and luxurious outerwear. By Lisa Armstrong

Portrait of Tammy Strobel

From top: Christian Dior fall/winter 2019; Chloé fall/ winter 2019; Gabriela Hearst fall/ winter 2019 

Is there a correct number of new-season pieces to buy to keep your signature look fresh and on point without your closet spilling over into SOS Marie Kondo territory? In an era when mindful consumption is increasingly becoming an urgent aspiration, you should think in terms of what will make the most impact, then strategise your spending accordingly.

This fall, I’d start with the feet because those cute ankle booties that have been your go-to for the past half decade may have just been nudged into the second row by taller boots. You can now channel après-ski in Chanel’s furry option that hits around mid-calf, or country-house chic with slim jeans tucked into CELINE’s cosy over-the-knee shearling-lined boots.

The thing about tall boots is that they won’t just retune your standard sartorial setting—they’re also a gateway to an alter ego. Consider, for example, Victoria Beckham, who used lipstick-red and leopard-print peep-toe thigh-highs to catapult her ladylike midi skirts and romantic blouses into an alternative universe where Nancy Pelosi borrows Beyoncé’s props. A glossy pair with a chunky heel can inject a hitherto conservative little skirt suit (Akris) or a grunge-acious fringed blanket skirt (Salvatore Ferragamo) with a dose of attitude. Conversely, tall boots confer some modesty in skin-baring situations, so Saint Laurent’s puffball shorts and mile-high hemlines and the barely decent minis at Longchamp and Max Mara start to seem viable.

Yes, skirts are back. In addition to the above, they come high-waisted and curvy, paired with fitted blouses at Burberry, or three-quarter length and worn with adorably prim little scarf-neck wool-and-cashmere knits at Dior. Gabriela Hearst’s bell-shaped midi skirts managed to be swishy, springy and unbelievably deluxe. Inspired by her rodeo-crazed mom, they’re bias cut and probably 200-ply alpaca. Nothing looks more elegant and relaxed with a pair of flat riding boots and a slouchy sweater. If you’ve missed the versatility of separates, this is the season to get back together with them. “I categorically refuse to design or wear anything that you can’t run or lie down in,” Hearst told me as we lounged on a cashmere sofa in her Paris showroom. 

My Reading Room

Chanel fall/ winter 2019 

If you’ve missed the versatility of separates, this is the season to get back together with them. 

My Reading Room

From left: Prada fall/ winter 2019; Salvatore Ferragamo fall/ winter 2019; Dolce&Gabbana fall/winter 2019; Alexander McQueen fall/ winter 2019; Givenchy fall/ winter 2019 

“I categorically refuse to design or wear anything that you can’t run or lie down in,” Hearst told me as we lounged on a cashmere sofa in her Paris showroom.

Even dresses are now required to behave like separates. Cut to skim and float around the body, many are expressly designed to glide under or over sweaters as well as work with jackets. At Chloé, Natacha Ramsay-Levi colour-coordinated them with fine-gauge turtlenecks, turning them into a kind of carefree dress suit. Donatella Versace unbuttoned her fluttery shirtdresses over pencil skirts and under silky corsets.

If you’re concerned that tailoring is taking a backseat, let me take you momentarily behind the scenes a few days before the Alexander McQueen show, where Sarah Burton was poring over 18 separate toiles, which is probably half the number it took her to perfect the label’s new squared-off shoulders. At just over 40cm from tip to tip, they’re assertive rather than aggressive. “That word doesn’t feel right anymore,” said Burton. “What’s nice is hearing so many of the models this season say how strong but also how comfortable they feel when they put on the clothes.” True strength doesn’t need aggression. Memo to angry tweeters everywhere.

“The shoulder is everything; it completely determines how a garment hangs,” Clare Waight Keller said backstage after her Givenchy show, which shone the spotlight on slender suits with high-waisted pants and belted jackets. High waists are everywhere, which is good news for those with short legs as they’ll look longer. Balenciaga is 100 percent behind the pantsuit too, playing with gender-fluid silhouettes and contrasting silk shirts. If that sounds tame for this label, there were more of those disruptive peaked shoulders (like Waight Keller, Demna Gvasalia has a shoulder fixation).

Rest assured, the jacket is still very much a cornerstone of your closet. Don’t get hung up on single- or double-breasted, either—go with whatever works for you. It’s the wide, arrow-shaped lapels and sharp shoulder that make a jacket feel modern. If you already own checks, try a flame-throwing colour (Balenciaga), a fabrication that borrows from military uniforms (Prada), or a shiny satin texture (Brandon Maxwell), any of which will boost its day-to-night capabilities. Utilitarian fabrics, luxed-up and sometimes embellished, are another facet of the flexi-dressing approach. At Dior, Maria Grazia Chiuri told me, “I try not to make things too precious. Even Dior customers want clothes that feel practical.”

This is not, you may be gathering, the season for twee prettiness. Not that florals have withered and died; from Prada’s big, ballsy blooms to Givenchy’s blurry clusters and Dolce&Gabbana’s drunk-on-life carnations, references have gone goth, as have the backgrounds they’re framed against. “The great thing about a black background,” Wayne Lee, one-half of the sibling duo behind the cult dress label Les Rêveries, explained to me, “is that you can wear them over dark hose.” Goth and pragmatic. Choose a substantial shoe such as Givenchy’s jolie laide platform loafers. If you must wear a kitten heel with a dress, make it a pair with dagger sharp heels like Miu Miu’s.

Finally, you should invest in a good cape, a blanket coat, a capelet, or an opera cape. Marc Jacobs went crazy for them all, as did so many other labels including Chanel and Prada. Some came with sleeves, some with belts (you’re going to need a wide one), while others were more like a cape-trench hybrid. And they’re ridiculously desirable. One-size-fi ts-all. One piece covers all eventualities. If you’re heading to Siberia, you could throw one over a coat. This multitasking exemplifies fashion now. Buy less. Buy clever. And may all your choices deliver a power punch. ■

Lisa Armstrong is head of fashion at The Telegraph (