7 Fabulous Fall Transition Pieces

Labor day has past and the official start of fall has begun. As those temperatures begin to sneak down we know that you, like us, are starting to think less about jean shorts and more about…well, jeans.

Right now is the perfect time to take inventory of your wardrobe and what key pieces you need from what’s been trending for fall. Maybe you’ve been a tad indecisive until now because you like what you see but aren’t 100% on how to style it?

Ladies, we got you. Our editors have identified seven great staple pieces that your fall wardrobe is craving. And just to give your inspo a much-needed push in the right direction, we’re also showing off some great ways to wear them!

Ready to fall in love with Fall?


Windsor, Classic Vibes High Rise Boyfriend Jeans $42.90

No big surprise, but since lockdown and the rise of comfort clothes, the era of the skinny jean seems to be coming to a close. Truth be told, baggier and loose jeans are giving our legs a well-deserved sigh of relief. The major front-runner to date is a fantastically updated 90s style loose-leg. Things to look for: a good high waist keeps the silhouette defined, a medium wash color easily works with casual and dressy, and while some destruction is still in vogue, the full-on torn knees look appears to also be heading towards the back of the closet.

Wondering how to style it? Here’s a combo that hits the right note of cool factor. Start with a super crisp white button down, like this one from Good American, and give it an edgy half-tuck in the front. Next, hit up some serious statement pieces like Krewe’s hand crafted sunglasses and some serious draping drop earrings from Baublebar. Round things out with a pair of stacked heel clogs, like these rich cognac ones from Beek.

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Windsor, Twist and Stun Knot Back Sweater $36.90

In what may seem a counter-intuitive move, negative space sweaters are showing up strong in fall. Leading the pack (no pun intended) is the open back sweater. The appeal is obvious – a simple enough look from the front until you turn and bam! goes the sexy. Things to look for: a solid color works best as it doesn’t distract from the attention of that negative space, don’t go for a low front and back (unless this is an evening look, in which case have at it) and definitely find some extra detailing around the back, like our find here from Windsor with a wonderful eye-catching knot.

Feeling a little intimidating on this one? Here’s a great way to style this for daytime – First, we need a bra that can keep you supported in this open back sweater without ruining the gorgeous view. Jezebel’s backless convertible bra will tackle that challenge with ease (plus it can be modified to fit all sorts of top types). Next we go bold with a fabulous plaid pant that adds a nod to sportswear with a cool grosgrain stripe and cuffed hems. Those cuffed hems are just begging for some amazing shoes and Windsor’s block heel booties do not disappoint. Last, we add a little whimsy with Tous’ punky take on their iconic bear. Bonus, it’s also an asymmetrical twist on standard silver hoops.

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Windsor, Go With It Ribbed Knit Crop Top $22.90

Let’s be honest…cropped has pretty much taken over the known universe at this point. So while you’ve probably been rocking your uber-cute cropped tees all summer, you may not have realized that you can easily take this look well into fall. Crops are so mainstream now that they can even be office-friendly…with a few rules ‘natch. Don’t believe us? Take this adorbs burgundy-brown beauty we found on Windsor. If you’re office is creative and casual (i.e. not super corporate) you could easily turn this into a fit that slays. Oh, and bonus – we’re also going to do a little one-stop-shop to make it even easier.

The secret to pulling off this look? It’s all about textures and proportions. Adding a cute, high-waisted mini skirt in a warm fuzzy plaid instantly makes the cropped sweater more peek-a-boo and less midriff baring. Then we get really creative by taking a full button down mini shirt dress, un-buttoning it completely and wearing it as an outer layer blouse-y jacket. Genius! Top the texture with some faux-suede knee high boots and really the only other thing you need is a good statement necklace. Like, say, the padlock necklace…which has been crushing the ‘gram for months now. Ta-DA! A fantastic fit from just one place. You’re welcome.

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adidas, Stan Smith Shoes $85

By now everyone has at least one pair of chunky trainers. They’ve been dominating the fashion scene since 2017. Major fashion houses sport their own versions and of course, the main stream brands have happily been churning out thicker versions of their steadfast sneaks. As with all things fashion however, the chunky trainers are starting to take a back seat, in favor of a return to sportier and retro inspired sneakers. Think of them as your NY street slice versus the previous season’s Chicago deep dish.

Power houses like adidas are releasing rebirths of some of their most iconic sneaks. But true to form, these updated versions have a 2021 twist, with materials coming from recycled and upcycled sources. Perhaps one of the most coveted at the moment is the timeless Stan Smith sneaker.

So the million dollar question is will these sneakers rise to the status of their Rubenesque-soled cousins? Will women be pairing their business suits and evening dresses with them? Short answer? They already are.

Here’s a perfect styling take on the look. We start with a gorgeous, rust colored midi dress with a fantastic neckline and just the right amount of stretch for a body con look that you can move in. Take the whole look to next level with a proper fuzzy coat (another big trend this season). Slide on some Oliver Peoples mega shades and then hit up some major layering with necklaces from Eye Candy LA, Adornia and Rina Limor. This look is pure drip.

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Windsor, The One-Belted Flannel Shaket $49.90

What’s thicker than your average top but thinner than your standard winter coat? Well, that would be fashion’s current favorite hybrid – the shacket (aka shirt + jacket…get it?). What started as a bit of an odd concept in fall of 2020, the shacket’s pleasing, easy throw-on silhouette has been growing in cult status all year. Fast forward to now, and the shacket has officially made the list of “must have” fall fashion for your fits.

Now, as you can guess, the shacket pretty much lends itself to casual. Our example above would look fantastic with a black tee and jeans, but we thought it would be cool to show you how you can take this plaid perfection and turn it into upscale office chic…don’t believe us?

Start by thinking of the shaket like you would a great blazer. A shaket is a bit on the warmer side, so going for a sleeveless black turtleneck seemed the logical choice. We pair that with some wide leg camel pants and a fab business belt. All that’s left is some office-worthy jewelry (pearls are a great go to) and some block heel loafers.

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Circus by Sam Edelman, Darielle Boot $100

A funny thing happened as our addiction to all-things-chunky heeled grew. We weren’t satisfied with combat boots and gorpcore gone extreme. Our cravings grew larger and as such, designers began “super-sizing” all sorts of boot styles. While we can’t say how long these will stay in the top position, we can say that as of right now it’s the luggy Chelsea boot that is giving everyone major swoons. So you may want to grab a pair as they are going fast.

And while these would look amaz-balls with jeans and a tee, take a daring cue from the internet influencers and pair it with a body con mini + a cropped super-puffy. We’ve put together a great example below, starring a super cute colorblock knit dress from Windsor which looks spectacular paired Stella McCartney’s cropped puffer jacket (it’s a cool collab with adidas, BTW). Add some toasty brown tights (because it’s fall, y’all) and finally some beautiful bling from Beverly Diamonds.

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The Kooples, Zipped Nylon Jacket $385

Motos and puffs aside, one of the most “welcome back” contenders for your jacket consideration is the flight jacket. Otherwise known as the bomber jacket, this season there are a multitude of variations to choose from. College style is very popular, as is of course, the traditional dark green version. But if you’re really looking to 2021 freshen this look up, we highly recommend a bright color pop version. Bright colors (hues you would normally associate with spring) are really trending this fall. This beauty we found on The Kooples is a brighter, happier version of the more common olive green, and was one of the popular colors appearing at the A/W New York Fashion Week for 2021-2022.

Not positive what you’d pair this with? As the model in the pic above shows, a jeans + white tee combo is an easy win to wear. But let’s really kick this up a notch, starting with a show-stopping, high-rise, flared patchwork jean from Levi’s RE/DONE collection. Upcycled pieces of vintage Levi’s denim give each piece a one of a kind look. We’re talking serious 90s vibes. So while we’re channeling some of the coolest moods from that era, we’re pairing this with Mott & Bow’s deep black, cashmere turtleneck. Add in some sweet stompers from M. Gemi, some gold dangle earrings by Rachel Glauber. Last (but def not least) a classic deep red-brown from NARS called, appropriately enough, Audacious.

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