For better or worse, trends have a way of making their way back around. Some, we’re happy to see again; others, not so much. From strappy Mary Janes and cargo pants to knee-high boots, these five fall and winter 2023 fashion trends will look familiar. We’ve decided to embrace them. Will you?

Long denim skirts

Denim skirts are showing up everywhere in a wide variety of lengths, washes, and rises. For cooler weather, opt for midi and maxi styles, dressing them down with fashion sneakers and a favorite tee, or dressing them up with a pair of sleek heels and a fitted top. This month, you can easily fight both high-waisted and slow-slung designs, making it easy to find an option that suits your body type and preferred silhouette!

model in black top and denim midi skirt
This denim midi skirt, $80 at Abercrombie & Fitch, is available in two washes — light (pictured here) and black. The midi length is a great way to show off a favorite pair of boots! Image: Abercrombie & Fitch
model in black top and denim skirt
Maxi denim skirts lend a little cool-girl edge to simple wardrobe staples. This front-slit denim skirt, $138 at Anthropologie, looks great dressed up with heels and an off-the-shoulder top but could just as easily be paired with boots and a white tank. Image: Anthropologie
model in striped top and black skirt
This flattering black midi option, $69.95 at Gap, is fitted at the waist and snug on the hip. Image: Gap
model in white shirt and jean skirt
Our splurge pick for this trend is the Ulla Johnson ‘Bea’ skirt, $490 at Revolve. The square pockets and button-front closure offer a hint of ’70s appeal. Image: Revolve

Tall boots

Booties took top billing for a while, and they’re very much still in fashion, but tall boots are back on the scene in a big way. Understated Western styles and knee-high boots with flat or sturdy block heels are great for pairing with skirts and dresses or layered over slim-fitting pants.

black knee high boots
This Dolce Vita boot is available in black, off-white, taupe, or tan for $99. While it has Western elements, we wouldn’t quite call it a “cowboy boot.” That subtlety makes this pair a chic, versatile wardrobe addition. Image: Zappos
slouchy brown knee high boot
Slouchy tall boots like these, available for $150 at Free People | Image: Free People
tan foldover boot
You can expect to see lots of foldover boots this season! This pair of Nine West dress boots, $199, will bring a hint of sophistication to your favorite printed dresses. Image: Nine West
black riding boot
Riding boots are back in the mainstream! This structured pair of Franco Sarto riding boots, $215 at Nordstrom, is at home in this year’s “quiet luxury” trend. Image: Nordstrom

Sweater sets (reimagined)

Since COVID, we’ve seen an uptick in the availability of stylish matching loungewear sets, and this time last year, we saw the return of the cardigan sweater set. This year, retailers are leaning further into elevated sets that are not only attractive but comfortable, and they’re great for mixing and matching. We’re highlighting sweater sets here in the spirit of fall, but you should also keep an eye out for sets in dressier materials — think silky skirts and tops and sophisticated suit separates!

model in brown skirt and sweater
Gap is offering a wide range of mix-and-match sweater separates in their CashSoft “cashmere-like” fabric. You can pair this midi skirt, currently on sale for $63 (marked down from $79.95), with a pullover sweater, a cardigan, or a vest. Most separates are also available in black and gray! Image: Gap
model in purple skirt suit
Channel Jackie Kennedy with this classic skirt ($198) and sweater ($178) from J.Crew. Paired together, the set is eye-catching, but the blazer would also pair well with jeans or trousers. Image: J. Crew
model in striped matching sweater and pants
This striped set from Free People ($277) channels the comfort of a COVID-era loungewear set, but it’s elevated for everyday wear. The model is relaxed here in loose waves and Birkenstocks, but you could easily dress this set up with the right shoes, bag, and a sleek bun. Image: Free People

Cargo pockets

Talk of the return of cargo pants began early this year, and with fall and winter fashion hitting the racks, the proof is in the pudding. Whether you’re looking for relaxed streetwear options or a new take on trousers for dressier occasions, a cargo style can lend a little interest to your look.

model in black top, cargo pants, boots
This high-rise slim cargo jean from Banana Republic lends a subtly chic safari appeal to any outfit. Choose from four shades — whiskey (pictured here), black, olive, and white. Regularly priced at $90, they’re currently on sale for $45! Image: Banana Republic
model in black wide leg trousers
To shop this trend for dressier occasions, opt for a pair of wide-leg trousers like these by Favorite Daughter — available for $248 at Revolve. Image: Revolve
model in black top and cargo pants
A nod to ’90s fashion, these low-slung straight cargo pants from Madewell are available in three shades and are currently on sale for $69.99-$82.50 (regularly priced at $98). Image: Madewell
model in jeans and green jacket
You’ll also spot more jackets and vests sporting cargo pockets this season. This lightweight cropped cargo jacket, $129 at Nordstrom, is a more current spin on the popular utility jacket from past seasons. Image: Nordstrom

Mary Janes

Feminine Mary Janes are back in the mix, available in a fun variety of fabrics and heel heights! Last week, we paid homage to flats for fall and winter, so you saw some great Mary Janes selections there. Today, we’re celebrating a more comprehensive range of options. It’s incredibly easy to find Mary Janes in versatile neutrals at the moment, but if you prefer a pop of color or patterns, you’ll be in heaven.

model in purple pants and shoes
Perfect for fall and winter, these plum velvet Mary Janes with gold detailing, available at Draper James for $125, can be dressed up or down for a wide variety of occasions. You can even rock these for after-five occasions, thanks to the velvet finish and gold detailing. Image: Draper James
black patent leather mary janes
These Mary Janes by Larroudé, $330 at Bloomingdale’s, feature a shiny patent finish, a comfy block heel, and a pointed toe. A super versatile way to invest in this trend! Image: Bloomingdale’s
leopard print slingbacks
These leopard calf hair Mary Janes with slingback straps at J.Crew ($218) are a fun way to add a pop of pattern to an otherwise neutral or monochromatic outfit. Image: J. Crew
printed mary jane pumps
Our splurge pick for this trend is the Sarah Flint block heel Mary Janes ($695) in an emerald jacquard print. These were designed in collaboration with influencer Grace Atwood — there are several other patterns and colors available, too! Image: Sarah Flint

Shop these trendy picks all in one place below!

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About the Author
Alissa Harb

Alissa is StyleBlueprint's Managing Editor. She's a Tennessee native and a lover of travel, red wine, and unlikely animal friendships.