It’s early September, the calendar insists fall has nearly arrived, but the weather? Not so much. Rather than crisp air and golden leaves, the end-of-summer into fall transition has offered prolonged bouts of heavy, humid heat, punctuated only occasionally by the fleeting mercy of cooler days. It’s that in-between space where dressing becomes a daily negotiation. And it’s the annual ritual my closet and I know all too well. So how do you nod to fall without sweating through your outfit by noon?

The answer lies in smart transition pieces. These are items that bridge summer’s ease and fall’s polish. This year I’ve pinned down my versatile staples that play both sides of the season. You can find them all on my SHOP page. And below are the 10 MVPs I’m relying on right now:

The Boxy Tee

When it comes to simple white tees, my search for the perfect one is anything but simple. I’m especially particular about this piece because the wrong tee can completely undermine a look’s foundation. Shape, fabric weight, neckline, and sleeve length all factor heavily into the equation. And a simple boxy tee like Buck Mason’s Field-Spec Boyfriend Crop Tee can be the anchor of any transitional wardrobe. Minimal, unfussy, but shaped enough to pair with more dramatic pieces.

The Longline Bermuda Short

Think of them as summer’s final word on tailoring. A pair like Aritzia’s Dossier Short that cuts just below the knee, keeps the silhouette elevated and breathable while offering more coverage than a classic short.

The Slim Sneaker with Personality

The statement sneaker moment isn’t going anywhere, but fall asks for subtle sophistication with slimmer silhouette sneakers taking over in pops of vibrant color. Try the Adidas Tokyo sneaker in blue suede. It has just the right mix of a classic silhouette in an unexpected, elevated material and color.

The Slouchy Suede Tote

Fall textures belong in the accessories first. The & Other Stories Large Suede Tote has that perfect, easy slouch and buttery brown suede that immediately nods to autumn. There are countless brown suede variations of this style. The fabric and no-fuss silhouette feels so luxe but understated. Definitely, a fall favorite in my book.

The Oversized Button-Up

If you’ve been following along with my style, then you know by now that I love my Levi’s. And the Levi’s Halie Boyfriend Shirt is a chameleon piece, equally at home as a swim cover-up, a layering shirt, or a breezy standalone top.

The Barrel Pant

I’ve really fallen in love with the barrel pant as of late. Few silhouettes feel as modern right now as this cut. The gentle curve at the leg offers structure without stiffness, and in twill, its ease makes it a natural alternative to denim when the heat lingers. The GAP Mid Rise Twill Barrel Pant nails the balance: crisp yet relaxed, versatile enough to pair with a crop tee for late-summer ease or an oversized button-up when the breeze finally cools. It’s the kind of piece that doesn’t fight the weather, it adapts.

The Rollable Raffia Hat

Rag & Bone’s Jade Whipstitch Hat is practical sun protection while still hinting at cooler weather with its structured finish. This one comes in several versatile colors. Rollable, travel-friendly, and nonchalant in the best way.

The Fishnet Mary-Jane

Aläia may have sparked the trend, but Stuart Weitzman’s Arabella Mesh & Leather Mary Janes perfects the look: breathable enough for warm days, with a black finish that transitions seamlessly into fall wardrobes on a mindful budget.

The Strapless Cotton Dress

As September clings to its summer roots, a strapless dress becomes more than just daywear but a lightweight lifeline. Take Mango’s Strapless Pleat Front Dress. It’s one of those quietly elegant pieces that opens up new styling paths: you can add a strappy sandal and suede tote for daytime ease, or elevate it with a pointed toe kitten heel mule or flat and light jacket

The Oval Sunglass in Tortoise Shell

Brown tortoise shell is my favorite print for eyewear. It feels distinctly autumnal but still works with sunlit afternoons. And an oval shaped frame is one that keeps the mood retro and unexpected. This Prada pair features a fresh take and mod nod with a colored/non-black lens.

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You can shop my entire summer-to-fall edit, including all of the items mentioned here, on my SHOP page.