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Summer to Fall Transition Pieces: 37 Dresses, Knits & Accessories That Work in Both Seasons
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items Nashville doesn't really do a hard stop between summer and fall — it's more like six weeks of “is it still 90 degrees or not.” So I built this list around the pieces that don't care either way: linen and poplin dresses in colors that read fall, cardi...
Sections
5
Dresses for the In-Between
Knits & Layers
Denim & Outerwear
Shoes & Bags
Jewelry & Accessories
Dresses for the In-Between
Cotton, linen, poplin, even a little silk — the fabrics that don't know if it's still summer or already fall. These are the dresses I reach for on the days Nashville can't make up its mind.
The embroidery along the neck and hem makes this feel more special than a $110 cotton dress has any right to. Sandals now, boots and a jean jacket in October.
Women's Embroidered High-Neck Mini Dress | Women's Dresses & Jumpsuits
Smocked bodice so it actually fits without sizing up, and the puff sleeves keep it from reading too summery once it cools off. Under $40 is basically free.
Puff-Sleeve Smocked Mini Swing Dress
Prairie dresses are the easiest fall pivot — long sleeves, midi length, dark charcoal colorway that leans straight into September. On sale under $30 too.
Fit & Flare Prairie Midi Dress
The ultimate transition piece: over a swimsuit at the end of summer, under a cardigan the second it cools off. Medium wash keeps it from looking stiff.
Denim Mini Shift Dress
Linen through Labor Day, easy. The puff sleeves and ivory floral keep it soft, not beachy — I'd wear this to a September wedding without thinking twice.
Linen Puff-Sleeve Maxi Dress
Stonewashed beige might be the single most useful color for a fall wardrobe — it goes with everything I already own. Comfortable in 90 degrees, still works layered under a jacket in October.
Cotton Poplin Maxi Dress
The one piece on this whole list I'd actually wear to work. Pleats give it movement, the blouson fit is forgiving after lunch.
Stretch-Cotton Pleated Midi Shirt Dress
The dress for the first cool night out. Semi-sheer mesh over a slip, black floral so it reads more fall than summer garden party.
Mesh Tie-Neck Maxi Dress
Silk satin in a midnight polka dot is exactly what I reach for once the light starts changing here. Cap sleeves and a V-neck keep it from feeling too heavy for the warm days still ahead.
o.p.t Kasey Silk Midi Dress
Had to include this one — it's my name. A textured crochet-style mini that feels like the dressier cousin of everything else in this section.
Madewell The Sophie Mini Dress
Knits & Layers
The cardigans, sweaters, and lightweight tops that make layering possible before it's actually sweater weather.
Loose fit, ruffled v-neck, a cream that works with every other neutral on this list.
Loose Short-Sleeve Top
SoftAF fabric, cropped fit, a crew neck and buttons instead of a zip. My new go-to for throwing over a tank the second the AC gets aggressive.
Women's Sunday Shrunken Cardigan | Women's Tops
Cotton and extrafine merino blend, so it's not too warm yet. The intarsia floral placket makes it look far more expensive than a basic cardigan.
Rails - Mavie Intarsia Floral Cardigan (Women)
This brown is the color I keep buying in every category this season. Oversized enough to layer a tee underneath on cooler mornings.
100% Cotton Oversized Sweater
A sheer, crinkled knit polo that reads more “elevated top” than “golf shirt.” Fitted enough to tuck into the denim shift dress above.
Crinkle Knit Polo
Cotton poplin, pintucked, sleeveless — the kind of top that looks finished with just jeans.
Poplin Pintuck Shell Top
Cotton lawn with a peplum hem, which does a lot of work for tucking-in purposes. Lace trim keeps it from feeling too plain.
Square-Neck Lace-Trim Peplum Top
An oversized white poplin shirt with a tie neck — I wear these open over everything from May through November.
Organic Cotton Poplin Tie-Neck Shirt
Waffle knit gives it texture so it doesn't look like a basic tee. $15 and it'll be in constant rotation under cardigans.
Fitted Waffle-Knit Cropped T-Shirt
The button-down I actually reach for — neutral stripe goes with denim, trousers, layered under a sweater, all of it.
Classic Button-Down Shirt
Denim & Outerwear
The bottoms and jacket doing the heavy lifting once the mornings get cooler.
My current denim pick — relaxed through the leg, high rise, and the medium wash works with everything from sandals to boots.
Women's High Rise 90s Relaxed Jean | Women's Bottoms
Chocolate brown denim with a drawstring ankle hem — a little dressier than a basic jean and exactly the color palette I want for fall.
PAIGE Arellia Pants
Barbour waxed cotton is the classic layer for exactly this weather window — breaks in beautifully and works over everything above.
Barbour Erma Waxed Cotton Jacket (Women)
Shoes & Bags
Neutral leather and suede that carries every outfit above from September into November.
A low kitten heel mule is my favorite fall shoe — dressy enough for the shirt dress, comfortable enough for an entire day out.
Dolce Vita Cleo Pointed Toe Kitten Heel Mule (Women)
A jelly flat with a tortoise finish so it doesn't read as summer-only. Easy with any dress on this list.
Jam Tortoise Jelly Flats
Mary-jane flats are having a moment, and suede in dark brown is the most-worn shoe color I own come fall. These go with literally everything above.
REYES Dk Brown Suede Mary-Jane Ballet Flats
Raffia texture keeps it from feeling too summery-straw while still working with the lighter dresses in section one.
Elm Natural Cross Hatch Raffia Flats
Chocolate suede tote big enough for actual daily use — laptop, water bottle, all of it.
MARO Chocolate Suede Tote Bag
Jewelry & Accessories
The small stuff that makes an outfit look finished — and travels easily between warm and cool days.
Lightweight sculpted puff earrings I can wear all day without my ears complaining. High-polish silver goes with the gold pieces below too — I mix metals constantly.
JENNY BIRD Mini Paige Puff Earrings (Women)
A stacking set so you're not buying pieces one at a time. Twisted design catches the light without being loud.
Set of 2 Twisted Bracelets (Women)
Brass with a dual-tone finish — small enough for everyday, sculptural enough to notice.
Madewell Sculpted Illusion Earrings
Semi-precious stone beads in a deep chicory tone. The heart charm keeps it from feeling too serious.
Madewell Puffy Beaded Heart Bracelet
Tiger eye is such a fall stone — warm, a little glowy. These are the earrings I'd wear with everything neutral on this list.
Heaven Mayhem Luma Knot Earrings
A round red agate stone on a simple chain — the one statement piece here that still layers easily.
Heaven Mayhem Sol Necklace
Gold-tone with an enamel detail, small enough for daily wear.
Heaven Mayhem Solara Earrings
Ties on a bag, in your hair, or around your neck — the cheapest way to make any outfit above look finished.
rag & bone Floral Western Bandana
Colorful resin beads on a goldtone chain, a pop of color against all the neutrals in this list.
BaubleBar Jane Beaded Necklace (Women)