20 Summer Dresses You’ll Still Love Come Fall

Seasonal shopping is tricky. On the one hand, you want to allow for some summer indulgences while reaping the benefits of fewer layers, but on the other, colder temperatures are just around the corner – so how do you make it work? By investing in summer pieces that can carry you into the fall with just a few easy tricks, you’ll be able to splurge in the summer and love your purchases right through to the fall. Read on as we take you through 20 summer dresses that you can buy now, and still love later!

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Aritzia

1 / 20

The easy-breezy shirt dress

What could be easier on a stifling hot day than throwing on this chic little number? Come fall, wear this with some leather leggings and a great wool coat to create an ensemble that amplifies the look for the season!

Wilfred Free Radhika Dress, $95

Model wears a light blue denim shirt dress

Forever21

2 / 20

The denim shirt dress

Denim has become a year-round staple, and the denim dress is no exception. To make this mini a little more cold-weather friendly, do up all the buttons, tie a printed scarf around your neck and throw on some stockings, or thigh-high boots.

Forever 21 Denim Shirt Dress, $40

Club Monaco

3 / 20

The silk dress

Don’t be fooled by the fabric – the silk slip dress is a must-have wardrobe staple and will absolutely get maximum use in the fall. Anything goes under these slinky dresses, so pair yours with a crisp white tee, turtleneck, or even a fun detailed poplin blouse.

Club Monaco Elizabella Silk Dress, $249

Model wears a longer length floral dress by HM with red boots underneath

4 / 20

The floral dress

If you thought “wallpaper florals” were a thing of the past, think again! Flower power is back and bolder than ever. Runways for both summer and fall showcased florals for all seasons in head-to-toe ensembles. The length of this dress makes it an easy piece to transition, and we love the look with a bold red boot underneath!

HM Patterned Dress, $50

Zara

5 / 20

The midi wrap dress

Floaty, flirty and fun, this has been the go-to style for celebs and fashion bloggers this season, and it’s not hard to see why. Expect this style to stick around well into the fall and winter months, dressed up for the season with statement belts and sky-high boots in place of stockings.

Zara Crossed Midi Dress, $70

Model wears a navy blue pyjama-style shirt dress with piping

Joe Fresh

6 / 20

The pyjama dress

This year has been all about the sexy not-so-subtle homage to lingerie for day-to-day, so the pyjama trend taking off was something of a relief for those of us looking to tackle the style – without baring so much. This piped shirt dress feels like the slinky pyjama shirt of our dreams, and for the fall, we’re swooning over the thought of pairing it with an exposed turtleneck underneath.

Joe Fresh Piped Shirt Dress, $39

French Connection United Kingdom

7 / 20

The sheer dress

Bold floral prints, ruffle-tiered skirts and peek-a-boo details are the stuff summer dreams are made of… but can they work in the fall? Absolutely – and here’s where simple stockings and slick patent booties are your best friend. Play off of that summer-vibe by adding the contrast of colder-weather materials like patent leathers and wool stockings to create a look that’s totally fall-appropriate.

French Connection Allegro Poppy Sheer Dress, $238

Model wears a light blue print tea dress with ruffle details

BCBG

8 / 20

The tea dress

The “it dress” of the season has to be the tea dress. Form-fitting in all the right places and flowy in others; there’s a very vintage feel about this dress fit, and one that we are loving for the coming fall season as well. As these minis are typically made of lighter-weight materials, try tucking the bottom half into a pair of high-waist relaxed-fit jeans for a fall look that will keep you looking both on-trend and classic-cool.

BCBG Mabel Floral-Print Dress, $350

Oak and Fort

9 / 20

The layered slip dress

Don’t you love it when a store just reads your mind? Oak and Fort, designers of the ultimate in effortlessly-cool fashion for budget-friendly prices, strikes again with this simple dress, shown in a layered style that is summer and fall-friendly all in one. If it gets a little chilly with just the short-sleeve tee, swap it out for a cute mock-neck knit, some stockings and oxford flats, for that prep-school-chic look.

Oak and Fort Slip Dress, $34

Aritzia

10 / 20

The t-shirt dress

What’s cuter for the summer than an easy t-shirt dress with some tennis sneakers? Nothing! So we swooned when we saw this pretty little number with the bonus tie detail in front from Aritzia. Tip: when you spend a little extra on basics, that quality will carry you into other seasons more easily – but luckily for us, this luxe take on the basic style from Aritzia is a quality knit and super affordable at under $40. Pair it with leggings, sneaks and a great oversized denim or bomber jacket for a fall spin on summer athleisure.

Aritzia Bair Dress, $32

Anthropologie

11 / 20

The gingham dress

Gingham has been everywhere lately, and while we love it best in the summer months, this pretty print still works well in the fall. Play off of the black or white in the print with complimentary layers under and over for a vintage-feeling monochromatic look that will keep you warm – and on-trend.

Anthropologie Gingham Flutter Dress, US $158

Nordstrom

12 / 20

The ruffled satin dress

Ruffles and satin – what could be sweeter for summer? We love the rich hue and fresh slinky feel of this dress, but before you store it away come fall, try pairing it with thigh-high boots and a trench for a date-night style that will sizzle even when it dips below zero!

Nordstrom Ruffle Sleeve Satin Dress, $99

Model wears an orange-red shift dress with short sleeves and a front-tie detail

Ted Baker

13 / 20

The red dress

Ok, so Ted Baker calls this one orange – but we’re seeing more of a tomato hue here. In any event, these punchy reddish shades are cropping up now, but will be MAJOR come fall, so get on board and layer this pretty dress with black stockings and booties when you start to feel the chill.

Ted Baker Papron Tie-Front Dress, $295

Zara

14 / 20

The bold print mini

This bold print polka dot dress from Zara is perfect as-is for an easy statement piece in the summer, but will really pop against the cold-weather neutrals you’ll layer over it in the fall. As soon as the temperature begins to dip, pair this dress with some opaque black stockings and on-trend sock booties for a look that’s effortlessly chic – and budget-friendly!

Zara Polka Dot Dress, $35

J Crew

15 / 20

The statement dress

This stunning dress feels more like wearing art than anything else, but before you write it off as a summer-exclusive for its blush hue and soft textures, think again! This season (and for many to come) the fashion forecast is all about mixed materials and the unapologetic colour-clash. So shimmy your way through every event this summer in this investment piece, and then pair it with some bold stockings and a leather jacket come fall!

J Crew Silk Sequin and Feather Dress, $1263

Additionelle

16 / 20

The colour-block shift

Colour-blocking is a great way to inject some fun into work-appropriate dresses like this one, which is a fun and fresh option for the summer but carries well into the fall with some easy additional layers.

Additionelle Michel Studio Color Blocked Dress, $95

Urban Outfitters

17 / 20

The straight-neck dress

Straight-neck details, both in dresses and blouses, have been a big trend all summer, and it doesn’t look as though this style is about to die down anytime soon. Taking the primary colour in this fitted poplin dress and pairing it with long-sleeved layers underneath gives it less of a summer-y feel and works well when remixing the style into the fall season.

Urban Outfitters Kimchi Blue Rae Straight Neck Poplin Dress, $74

LOFT

18 / 20

The swing dress

Think of the swing dress as an elongated oversized tank top; lightweight and casual for summer, but so much potential with the right accessories in the fall. Bold, belted looks are back and will cater to the more structured styles coming in the fall.

Loft Sleevless Swing Dress, $65

Style Stalker

19 / 20

The classic shift

An office-style favourite (when worn at a work-appropriate length), the shift dress has come a long way. No longer shapeless and available only in bland neutrals, the new shift subtly nips in all the right places and can be super flattering when done in the right fabrics and the right cut for your body type. This one in a print is perfect for any season, but for a fall update, try pairing it under a fitted cardigan in a contrasting print for some extra warmth and added style.

Style Stalker Dark Surf Shift, $179

20 / 20

The velvet dress

More of a cold-weather fabric to begin with, the influx of velvet designs this summer has made it easy to plan for those luxe fall ensembles. This one is a no-brainer – velvet is probably trickier to pull off in the summer because you won’t want to wear it on a super hot day, but come fall, you’ll be glad to have it! This one’s on major sale, so ready – set – GO!

HM Velour Dress, $25