20 “summer into autumn” appropriate vintage dresses

One day the sun has you reaching for the shade a parasol provides, the next nippy winds and spitting rain have you diving under your umbrella. Capris seem appropriate one moment, yet seconds later you’re wishing for flannel lined jeans. Not entirely summer, but not quite full on autumn either. Eager to get a precocious start out of the gate, signs of fall sometimes appear as early as late August or the start of September, yet it generally takes a few more weeks for all elements of summer to vanish entirely.

During this indecisive time it can be tricky to select what to wear each morning. Too light an outfit and you risk freezing both indoors and out (especially if you’re in a highly air conditioned building), too heavy and you might suddenly feel like it’s July again. The key to dressing for this “in between” season is to pick medium weight fabrics, pieces that layer easily (cardigans, twin sets, etc), light to medium weight hosiery, pieces with elbow length or longer sleeves, and dresses with more substance to them than summer frocks but not so much bulk that they could keep January’s chill entirely at bay.

Loving dresses as passionately as I do, this post is going to focus on end of summer-slash-start of autumn appropriate frocks. Naturally the weather and climate of your own part of the world will factor into what kinds of clothing choices work best for you during this fickle time of the year, but in general I find that for the unpredictable nature of a Canadian climate (where snow in October is certainly not an unheard of occurrence), the following kinds of dresses can really work well throughout September and into early October.

The selection of frocks below are all either genuinely vintage or contain elements that lend them a telltale sense of vintage style. When looking for such types of dresses yourself, be sure to hit vintage stores, thrift shops, and consignment boutiques at this time of year, as autumn appropriate wear begins to be cycled into such stores stock. The sooner you start your hunt, the more likely you are to find great dresses before the masses have begun yearning for autumnal pieces, too.


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{Move over summer, autumn might just be the new hottest season in town with sultry body hugging frocks such as this sweet-as-chocolate brown number! “Heartbreaker Fashion Brown Knit Super Spy Dress”, currently available in sizes XS and XL, $59.95 (US) from Babygirl Boutique.}



{This long sleeved dress looks immensely contemporary, yet, according to the seller, hails from the late 1930s or early 40s. Sporting a cheekily fun pattern of leaping deer and flowers, this olive and purple hued silk frock could easily be worn on its own or paired with tights and a light coat to take you into the cooler days of fall. Silk print, keyhole neck dress vintage dress, fits up to a 29” waist/34-36” bust, $125.00 (US) from Viva Vintage Clothing.}



{With its built-in capelet and knee length A-line skirt, this classy and classic 1940s inspired dress would be wonderful for a diner date, night out on the town, or cocktail party. Black “Eva Bow Dress”, available in sizes small through to 3X, $138.00 (US) from Unique Vintage.}



{During the 1940s and into the 50s, a popular style of dress that was often seen in catalogues (think Sears) and fashion magazines was the coat dress. Styled like a fitted ladies coat, but made from lighter fabrics and intended to be worn on its own or under a coat, this style was both feminine and often a lovely way to stay warm on breezy fall days. This slate grey vintage coat dress is made of a lightweight wool, fits up to a 32” waist/41” bust, and is adorned with two decorative silver hued buttons near the lapel. I adore this style of frock and could just image how lovely a piece this would be to wear all autumn long. $135 (US) from Vintageous.com.}



{Cute as a button! This longer length dress with built in bolero style sleeves and ruffled hem is so sweetly beautiful. It’s cheery red pallet instantly calls to mind thoughts of candy apples and crisp maple leaves blowing down the sidewalk. “Red Plaid Belted Lucy Dress” available in sizes 36 to 46 (which are akin to 4-6 through to 18, according to the site’s sizing chart), $39.95 (US) from Chic Star (note, this same style of dress is also available in a black and white version).}



{A tranquil pallet of wonderfully autumnal hues adorn this classic 1950s shirtwaist dress, making it so easy for you to pull colours from this pattern for use with shoes, cardigans, handbags or accessories. Vintage striped “Toni Todd” dress, fits a 28” waist/38” bust, $65.00 (US) from etsy seller Timon Michelle.}



{This dark blue and green dress, simple as it may appear at first glance, is in fact captivatingly beautiful and ripe with wonderful details such as buttons all the way up the front and feminine tailoring. Vintage 50s “Lucy Plaid” dress, fits 26” waist/36” bust, $89.00 (US) from Planet Claire Vintage.}



{Classic tailoring (that calls to mind many 1940s styles) and figure flattering ruching combined with the rich coffee brown hue of this ¾ length sleeve dress add up to create the sort of frock you’ll happily reach for year after year. “Julian Taylor Ruche Waist Dress”, currently available sizes 6, 8 and 14, $57.77 (CND) from Overstock.com.}



{A strikingly lovely rust-meets-pumpkin hue colours this long sleeved, full skirted, button front frock in the perfect shade for September, October and November. Vintage faille shirtwaist dress, fits 28” waist/38” bust, $145.00 (US) from Couture Allure.}



{Shades of purple and green take on a muted tone in this classic long sleeved shirtwaist style dress. I could easily imagine pairing this frock with cardis and coats in shades of cream, brown, green, purple, and camel for days when you needed a hint more warmth. Vintage 1950s dress, waist 26”/bust 36”, $52.00 (US) from etsy seller Jewels 4 Pandas.}



{A wonderfully classic cap-sleeve, fully lined sheath style meets an autumnally appropriate shade of crimson in this lovely dress, which would be great for everyplace from the office to a candlelit supper just for two! “Jessica Belted Dress” available in sizes 6 to 18 (in petite and average sizes), $69.99 (CND) from Sears.ca (same style also available in black).}



{Looking fantastically like a piece that could have come right off the stage of Mad Men (not to mention this season’s catwalks where houndstooth is currently in vogue again), this vintage black and tan dress is unlined, but could easily be worn with a slip beneath and a cardigan or lightweight coat over top. Early 1960s cotton houndstooth dress, fits a 38-40” waist/44 to 46” bust, $50.00 (US) from Viva Vintage Clothing.}



{Two classic hues comprise this charming lightweight corduroy 1950s dress that sports generously sized pockets, a stand-up collar (which can be worn flat, too), and a cute little matching slim width belt. Red and navy blue corduroy dress that fits a 29” waist/37” bust, $89.00 (US) from Vintageous.com.}



{A little alluring, wonderfully timeless and entirely gorgeous, this dress looks as though it could have been worn on the back of a 30s or 40s Hollywood starlet, yet is a modern frock with a hint of stretch to ensure it hugs your figure just right. “Curves Ahead” dress available in sizes XS to XL, $137.99 (US) from ModCloth.com.}



{A pattern of quintessentially fall foliage adorns this lovely tie waist, button front dress complete with a swooping fully skirt and shirtwaist style tailoring. Vintage “Autumn in Paris” dress, waist 32 to 36”/bust 42”, $34.00 (US) from etsy seller Nod to Mod Vintage.}



{Imagine that this pretty model isn’t wearing gladiator-esque shoes, but rather t-strap or d’Orsay pumps and the 1950s bombshell (think Marilyn or Jane) appeal of this light grey dress instantly jumps out at you as being a great early autumn piece (thanks to its longer sleeves and becoming pleated hemline). Fully lined “Paloma Belted Dress” available in sizes 14 to 30, $128.00 (US) from Igigi.com.}



{A subdued, classic plaid pattern in blue and grey covers this schoolgirl inspired dress, which features dolman sleeves and four large buttons up the front. 1950s “Prep School” dress, waist 28”/bust up to 40”, $42.00 (US) from etsy seller The Greedy Seagull.}



{Called the “Joan” and looking every bit as though it could have come from this stylish Mad Men vixen’s closet, this brown herringbone plaid dress with matching belt would hug all your curves yet still be office appropriate all autumn long. “Joan Dress in Profession”, available in sizes 0 to 12 (though at the time of writing, only size 2 is in stock), $89.99 (US) from ModCloth.com.}



{The moment you spy this two tone frock, you’re stuck by the fact that it clearly telegraphs a distinctly vintage vibe befitting a woman who loves styles from the mid-twentieth century. Grey and black “Diamonique” crepe dress available in sizes extra small and small (it’s currently on clearance, so hence the lack of a greater selection of sizes), $86.70 (US) from Plasticland.}



{A rich array of green and brown autumn inspired hues adorn this beautiful 1950s wiggle dress, whose long skirt, elbow length sleeves, and conservative neckline would make it perfect for those cooler fall mornings when you want to feel covered up but aren’t quite ready to dig out the winter coat yet. Vintage “novelty print” dress, 35” waist/43” bust, $34.00 (US) from etsy seller Timon Michelle.}


When selecting dresses for this time of the year, as the examples above help to illustrate, it’s wise to look for pieces that have at least one element (lining, longer skirt and/or sleeve length, heavier fabric, higher necklines, etc) that sets them apart from sun dresses, so that they’ll be able to help carry your wardrobe from autumn into winter (and/or be appropriate for spring weather as well).

However that said, do keep in mind that some summer frocks can still work into the fall if you layer other pieces under (turtle necks, button down skirts, blouses, etc) or over them (such as cardigans, boleros, shawls, shrugs, stoles, and lightweight coats). I personally find that if I have to opt between being a little chilly or being a tad warm, I’d take warm anytime. It’s easier to fan yourself with your pocketbook while waiting for the bus than it is to have to stomp your feet and shuffle from foot to foot (all the while blowing hot air onto your hands to keep them from turning blue) in an attempt to warm up.

Always more of a fan of cool weather dressing than summer styles (gorgeous as many summer looks can be), I for one am tickled pink about the arrival of September and the need for “in between” season dresses and pieces of all sorts. I’ll be keeping my eyes peeled for bargains on dresses that fit into this category over the next few weeks, while toping my existing frocks with cardigans and pairing some styles with blouses and turtlenecks underneath.

What kinds of dresses and other types of wardrobe items do you love to sport during these lovely weeks when summer gives way to autumn’s arrival?