15 Ways to Style a Dress This Fall

My dresses do not get put away in September. I’ve tried. Every year I end up digging the silk slip back out by the second week of October, because 62 and sunny is dress weather and I don’t care what the calendar says. So this year I’m skipping the drama. A dress can go the distance from the first cool morning to the first frost, provided you know what to throw over it, under it, and on your feet. Fall is all texture: suede jackets, chunky knits, western boots, felt hats, and a seventies boho mood that has been drifting through runways and every Instagram feed for a few seasons. Layering is the whole point of the look, which means the dress you wore in August is a foundation, and everything you add is where the styling happens. If you’re still shopping for the dress itself, start with our fall dresses under $100 guide. Then come back here, because these fifteen looks already did the hard part. I’ve lined them up in order, from a sweater draped over the shoulders now to sheer tights on a November night out. Consider this your (very chic) weather forecast. Evie’s product selections are curated by the editorial team. If you buy something through our links, we may earn an affiliate commission, at no cost to you. We only recommend products we genuinely love. With a sweater over the shoulders Shop the look: Dress (Free People, $118) | Beanie (Free People, $30) | Sweater (Naadam, $98) | Sunglasses (Le Specs, $75) | Bag (Coach, $295) The first cool morning calls for the gentlest layer, and @amberdowty_ started with a slip made for bedtime: her exact Free People mini, silky, tiered and lace-trimmed, worn in daylight under a white sweater knotted over the shoulders and a crochet beanie. The brown hobo is her Coach Brooklyn 28. It’s 58 at breakfast and 75 by lunch, so the sweater handles the walk to coffee and comes off by noon. Get the look with a Free People crochet cap in antique ivory and Naadam’s white cashmere crewneck. Knot the sleeves low. With a plaid shirt jacket Shop the look: Dress (Cleobella, $214) | Shirt jacket (Frank & Eileen, $258) | Flats (Dolce Vita, $135) | Bag (Cuyana, $298) | Sunglasses (Meller, $49) | Earrings (Olive + Piper, $38) @matildadjerf keeps it Scandi-simple for the first week of September: a lace-trimmed white mini, an oversized mustard plaid shirt jacket worn open, sleeves pushed up, butter-yellow ballet flats, a cream leather tote, brown sunglasses, and pearl studs. The shirt jacket earns its spot: warm enough for a breezy morning, gone by the time the afternoon hits 75. Recreate it with Cleobella’s Nisreen babydoll mini, Frank & Eileen’s plaid shirt, Dolce Vita’s Ronen flats, Cuyana’s Classic Easy tote, Meller’s Binti sunglasses, and Olive + Piper’s pearl studs. Keep it unbuttoned so the dress still gets its moment. With socks and loafers Shop the look: Dress (Princess Polly, $64) | Socks (Eberjey, $28) | Loafers (G.H. Bass, $195) | Bag (Staud, $250) @emmaleger did the Manhattan-sidewalk version: a brown-and-cream check short-sleeve mini shirtdress, white crew socks, black penny loafers, a structured black leather shoulder bag, and wired earbuds (very 2005). Short sleeves and bare legs make sense while September still feels like summer, and the socks and loafers add just enough coverage to say fall is coming. Get the look with Princess Polly’s Motley brown plaid shirt dress, Eberjey’s ribbed crew socks, G.H. Bass’s black Whitney Weejuns, and Staud’s Ollie bag. Scrunch the socks so they sit low at the ankle. With a crisp white shirt Shop the look: Dress (& Other Stories, $179) | Shirt (Splendid, $97) | Tights (HUE, $20) | Boots (Mint Velvet, $180) | Bag (Cambridge Satchel, $105) | Earrings (Caitlyn Minimalist, $33.75) @deboraahmarie’s pinafore trick: a black-and-white houndstooth sleeveless shift layered over a crisp white shirt with blousy sleeves, sheer black tights, black knee-high boots, a small oxblood crossbody, and gold hoops. It’s the first early-fall evening that asks for tights, and the shirt gives a sleeveless shift its sleeves back while the boots handle the rest. Recreate it with & Other Stories’ houndstooth dress, Splendid’s Reese button-down, HUE’s black tights, Mint Velvet’s Harley boots, Cambridge Satchel’s Pushlock, and Caitlyn Minimalist’s Anine hoops. Size up on the shirt so the sleeves billow. With burgundy booties Shop the look: Dress (FARM Rio, $280) | Boots (Dolce Vita, $240) | Bag (Teddy Blake, $370) @emilyreavess went long for September: a fluid paisley maxi in rust and olive, pointed burgundy ankle boots, and a brown leather shoulder bag. Long sleeves handle the cooler evenings, while the lightweight fabric keeps warm afternoons from getting sweaty. The boots do the seasonal heavy lifting, pulling a summer silhouette into fall. Recreate it with FARM Rio’s Borbofly maxi, Dolce Vita’s burgundy Danity booties, and Teddy Blake’s brown suede bag. Pick a boot a shade deeper than the print’s warmest color so it all reads as one outfit. With a leather bomber Shop the look: Dress (Red Dress, $92) | Jacket (Mint Velvet, $350) | Heels (Valentina Rangoni, $210) | Bag (Mansur Gavriel, $525) | Sunglasses (Meller, $49) | Earrings (Olive + Piper, $52) @styledsara wore ivory satin to Brandon Maxwell at New York Fashion Week: a bias-cut slip midi with a lace hem, toughened up with an oversized black leather funnel-neck bomber, black pointed pumps, a slouchy black bag, tiny cat-eye sunglasses, and crystal cluster earrings. Get the look with Red Dress’s satin lace slip, Mint Velvet’s funnel-neck bomber, Valentina Rangoni’s Fiona pump, Mansur Gavriel’s Mini Candy bag, Meller’s Oza sunglasses, and Olive + Piper’s crystal studs. Zip it halfway. With a fringe coat Shop the look: Dress (FARM Rio, $104.50) | Coat (Sam Edelman, $139.99) | Hat (Gigi Pip, $146) | Boots (Durango, $99) | Bag (DONNAIN, $50.66) @thedailymadl took the western thing seriously. Over a black maxi with rust and amber florals, she draped her Sam Edelman fringe shawl-collar coat, added a grey-tan rancher hat, burgundy western boots, and a little suede crossbody. For a September weekend that starts warm and ends with a sunset chill, the coat sits on the shoulders first and goes on properly once the sun drops. Get the look with FARM Rio’s Black Lili maxi, Gigi Pip’s Monroe rancher, and Durango’s Shyloh boots. With slouchy knee boots Shop the look: Dress (Spell, $349) | Jacket (Böhme, $118.50) | Scarf (Böhme, $16.75) | Boots (Steve Madden, $169.95) @tijanserena’s rust paisley maxi is Chloé-coded, and the styling backs it up: an oversized dark chocolate suede jacket, a printed scarf knotted at the neck, and slouchy kitten-heel knee boots. By late September the boots do real work, covering the gap between hem and ankle that a breeze loves to find. Recreate it with Spell’s Damask button-through gown, Böhme’s Lovelyn suede jacket and Brenna bandana, and Steve Madden’s Lennox boots in brown suede. Scrunch the boots down. With jeans underneath Shop the look: Dress (12th Tribe, $88) | Jeans (AGOLDE, $238) | Jacket (Petal & Pup, $129) | Sunglasses (Le Specs, $109.99) | Earrings (En Route, $32) Gigi Hadid, via @thecoolhour, turned a sheer ivory lace maxi into a tunic by tucking it into horseshoe jeans, then added a slouchy tan suede jacket, oversized black sunglasses, and gold hoops. It’s the October daytime trick: the dress keeps its romance, the jeans add warmth, and the curved leg stops the proportions from going prairie. Recreate it with 12th Tribe’s lace maxi, AGOLDE’s curved-leg jean, Petal & Pup’s copper faux suede shacket, Le Specs’ sunglasses, and En Route hoops. Tuck loosely so the hem blouses a little. With a matching knit skirt Shop the look: Sweater (Princess Polly, $75) | Skirt (Edikted, $14.40) | Heels (Billini, $85) | Bag (Cambridge Satchel, $145) | Sunglasses (Quay, $80) | Earrings (BaubleBar, $38) @styledsara’s Milan look is the dress-adjacent entry, a knit set that reads as one piece. At Max Mara she wore an olive brushed mohair V-neck sweater with its matching mini skirt, black pointed slingbacks, a burgundy top-handle bag, dark cat-eye sunglasses, and gold knot earrings. October daytime suits it: bare legs still work, and mohair feels like a treat. Recreate it with Princess Polly’s V-neck sweater, Edikted’s fold-over knit mini, Billini’s Ayla heels, Cambridge Satchel’s Mini Poppy, Quay’s Bad Habit sunglasses, and BaubleBar’s knot earrings. Match the shades so nobody clocks the seam. With knee-high boots Shop the look: Dress (Cara Cara, $495) | Sweater (Gap, $69.95) | Belt (Petal & Pup, $29) | Boots (Vince Camuto, $239) | Clutch (Loeffler Randall, $325) @simplicatedsteph’s crisp-afternoon formula: a corduroy shirtdress mini in a gold, rust and teal baroque patchwork print, a burgundy crewneck knotted over the shoulders, a brown belt at the waist, mahogany knee-high boots, and a toffee suede clutch. The dress, sweater, boots and clutch are all her exact pieces: Cara Cara’s Villena, Gap’s CashSoft crew, Vince Camuto’s Sangeti, and Loeffler Randall’s Corrine. The boots cover what a mini leaves exposed in October, and the belt gives a shirtdress a waist. Petal & Pup’s classic brown belt stands in for hers. With rain boots Shop the look: Dress (Petal & Pup, $79) | Cardigan (Böhme, $68.50) | Rain Boots (Hunter, $190) Apple picking has a dress code, and @hattycakes wrote it: a burgundy plaid puff-sleeve mini, a chunky cream knit tied over the shoulders, matte burgundy rain boots with white lace cuffs, and a wicker basket. Mid-October orchards are muddy, chilly in the shade, and full of people taking photos, so this covers every base. Recreate it with Petal & Pup’s Yaris plaid mini, Böhme’s Markie cream cardigan, and Hunter’s Original tall boots in dark red. Add a lace boot cuff; it softens the rubber. With a belted blazer Shop the look: Dress (Show Me Your Mumu, $178) | Blazer (VICI, $84) | Belt (VICI, $38) | Heels (Dolce Vita, $99.90) | Bag (JW Pei, $149) Office to dinner is the slip dress’s whole reason for existing, and @m.g._style proved it: a black satin slip maxi, an oversized black blazer cinched with a gold-buckle belt, gold pointed slingbacks, and a quilted mini bag. By late October the blazer stays on all day, and belting it turns a boyfriend shape into something with a waist. Recreate it with Show Me Your Mumu’s satin maxi, VICI’s blazer and gold-buckle belt, Dolce Vita’s gold heels, and JW Pei’s quilted bag. Belt at the natural waist so the blazer blouses. With a chunky knit on top Shop the look: Dress (Quince, $109.90) | Sweater (White Fox, $79.99) | Bag (JW Pei, $109) | Heels (Larroudé, $350) @anastasiagerrans did the smart thing with a bias-cut silk maxi once the first truly cold days arrive: she put a chunky burgundy sweater over it, tonal head to toe, with a gathered dark brown leather bag and burgundy patent pumps. The sweater covers the shoulders and arms, the silk keeps the hem moving, and the monochrome makes it look planned. Recreate it with Quince’s wine silk maxi slip, White Fox’s burgundy knit, JW Pei’s Bella bucket bag, and Larroudé’s Ines pump. Front-tuck the knit so the waist survives. With sheer tights Shop the look: Dress (Show Me Your Mumu, $178) | Tights (Swedish Stockings, $25) | Bag (JW Pei, $129) | Heels (Alohas, $170) The first frost, a November night out, and @gabyite still in a mini: a sheer plum chiffon high-neck dress with blouson sleeves, sheer dark brown tights, a glossy burgundy baguette bag, and dark burgundy pointed patent heels with buckle straps. Tights are the whole secret, adding a layer of warmth without changing the silhouette, and the long sleeves handle the rest. Recreate it with Show Me Your Mumu’s cranberry chiffon mini, Swedish Stockings’ sheer tights, JW Pei’s burgundy bag, and Alohas’ burgundy buckle slingbacks. Keep the tights sheer; opaque turns chiffon into a costume.