I need to open today’s post by paraphrasing Carrie Bradshaw (but like, season 4 Carrie, if that matters. Stick with me here!): “There’s a time of year when, even before the first leaf falls, you can feel the seasons click,” she says (in a dramatic nighttime monologue, of course). “The air is crisp, the summer is gone. And for the first night in a long time, you need a blanket on your bed.” And she’s right! I don’t know what the weather’s like where you are, but we’ve finally hit that autumn inflection point here in LA. Temperatures have dropped from the mid-90s to the mid-70s, there’s a cool breeze at night, and it just feels like fall. Can you relate?
If so, today’s roundup is for you – we’ve scoured the market to find 22 incredible fall dresses, all with some sort of sleeve. They’re perfect for staying a little warm on a crisp night; for feeling pulled together and comfortable in your office; or, if you’re like me, for hiding any tattoos that you’d rather not talk about ad nauseam. (Don’t get me wrong – I love what I’ve added to my arms, but you can only answer “what does it mean?” or “did it hurt?” so many times, you know?) ANYWAY. Enough about me, my tattoos, and my long-term love of 1990s HBO comedies. Wanna see some cute dresses?
Full disclosure: despite my best efforts to be fully at peace in my body, there are still days where I get dressed and feel frustrated with how my clothes look and feel. The best antidote I’ve found? Scrapping whatever outfit I’d envisioned in favor of a classic, structured dress with a defined waist, just like this one. I love the sleeves (a little volume, but not linebacker-y), the cut, the pockets, and the material – it’s the perfect choice to keep you warm all winter long. (Bonus: this dress comes in a few other shades through size 22, and Boden also offers a bonus discount for teachers, students, first responders, and military personnel. They also carry lots of other cute sleeved options, if you’re in the market!)
Is Sezane expensive? Uh, YEAH. But if you have the budget to spend, they also make high-quality pieces that’ll stand the test of time. (Case in point: Em’s Leana dress from Sezane – currently sold out, unfortunately – which still looks and wears like new, despite repeated washings.) The Sadie dress you see above is perfect for fall, though – the blue and beige tartan is a fresh take on a classic autumnal color scheme and it’ll be easy to layer all season long. Keep it unbuttoned as a topper; pair it with a chic belt bag to add some shape; throw a cozy sweater up top (might I suggest one from this post?) and build out an effortless layered look.
SO COOL. When people say “effortlessly chic,” this is what they’re talking about! Throw on some sneakers, some loafers, and a hat – you’ll be totally ready to float out the door in a matter of minutes. (This one also comes in a high-end camel and black stripe, and I love how they styled the look out with some cute motorcycle boots!) I’ve really appreciated the shift towards more relaxed styles – it kind of rocks that it’s finally ON-trend to wear a comfortable dress with some breathing room.
But if you still enjoy a more fit-and-flare option (it’s my preference, too), GET A LOAD OF THIS CUTE PICK. It comes in 8 different colors and patterns through a size 24 – the tartan version, in particular, is a standout (only $89 right now and perfect for the holidays!) – and it’s an absolute workhorse. Could this be office-appropriate? Absolutely. But could you also wear it to a dinner with the in-laws, or to a PTA meeting, or to brunch, or to a fancy date night with your partner? YOU SURE COULD. (PS. If you’re worried about cleavage, take a peek at some of the models – they feature the dress on women of all shapes and sizes, so you can get an idea of how much coverage it provides to larger chests. It’s a good one!)
Okay – as a person who has stalked the iconic, oft-sold out Hill House Home Ophelia Dress for years, this was a HUGE FIND FOR ME. Quince has brought us the same look and the same high-quality construction (it’s 100% cotton, baby!) at almost ONE-THIRD OF THE PRICE. I know this might be a touchy subject for folks – dupes often are, and we can definitely talk about it in the comments! – but as someone who couldn’t really justify dropping $200 on a milkmaid dress that would only be worn once a month at best, stumbling upon this affordable alternative was SUCH A DELIGHT. (Pro tip: if you’re between sizes, order the smaller size. Trust me!!!)
If you’re skimming this post like, “Caitlin, girl, why are you giving us back-to-back “little lad who loves berries & cream” dresses?” then here’s my counterpoint: THERE ARE DOZENS OF US who like dressing like we’ve stepped off the set of a viral 2007 commercial. DOZENS! Let us have our moment. I love this updated version of a shirtdress – it’s pretty specific, yes, but it’s also a really fun blank canvas with a little built-in personality (you know, for the days when accessorizing just feels like too gargantuan a task).
ALRIGHT. BACK TO REALITY. For your consideration, I’d like to present a classic shirt dress – this one comes in three colors (the white is more expensive, FYI), but I’m especially partial to the rich tone of this loden version. (How cute does it look with those flats, too?) If you’re curious about how this will wear over the coming months, I really love the “How to Style It” feature on Madewell’s website right now – there are some VERY cute ideas that totally transform the look and feel of this dress! (I love the tall boots + blazer look, personally.)
OBSESSED. I know we normally reserve florals for spring, but the tones in this dress make it the perfect contender to pair with a bright and cheery pair of tights this fall (and plus, you’ll be able to wear it year-round once temperatures heat up again!). Plus, if stamped block prints are more your thing, this one also comes in a more simple black floral version. (The reviews are overwhelmingly glowing, too, for the record.)
HI BARBIE. This office-appropriate number is available through size 24 (hooray!) and the construction is just SO. DARN. CUTE! I know it’s on the expensive end of the spectrum for this post, but the tailoring here is to die for – I love the nipped waist and the a-line skirt. (It looks more form-fitting on the model than it does in real life – take a peek at the product shot to get a better idea of how the bottom half fits.) This one makes me wish that EHD had more of a corporate culture because NOBODY could tell me ANYTHING if I was wearing this dress in the office – it makes me want to grab an old school cellphone and make some DEALS. Obsessed.
If flow is more your thing, this maxi dress may be right up your alley – the olive tone is perfect for this time of year and you can tweak this dress to fit your modesty preferences. Leave the button-front open to show some skin; loosen the waist tie after a big burrito lunch…gotta love a dress that works with you, don’t you think? (PS. This is from one of Em’s new favorite brands, Emerson Fry – y’all have loved their block print tops in particular, but they make REALLY cute dresses, too!)
OOPS. My hands slipped, and then I accidentally typed out my credit card details, and then somehow, this dress showed up AT MY HOUSE only a few days later. CRAZY HOW THAT HAPPENS, HUH? (I must enter some sort of dissociative state when I see a bow. I’m a total sucker.) Anyway – THIS DRESS IS SO DANG SWEET. The “babydoll” term is a bit of a misnomer, I think, as it falls a bit closer to my natural waist and flares out in a really nice way. It’s been hard to find a denim dress that works for my specific style and I’m just thrilled with this one!
Have you ever seen a dress like this on a model and been like, “well, she looks cool styled like that, but I couldn’t pull it off?” Because I’m here to tell you the honest truth: YOU DO LOOK COOL AND YOU CAN PULL IT OFF. All that negative self-talk is just in your head! (This is a note to myself, too, for the record.) Scroll through the gallery and see for yourself – this dress looks SO refined and polished on women of all shapes, styles, and sizes.
Simple, affordable, and easy-to-wear – what else can you ask for? FYI, Gap also carries a rich burgundy and navy plaid version of this dress in addition to the timeless black-and-white and blackwatch versions pictured here. (Did anyone else rock some classic navy and green blackwatch in their high school uniform? It was the plaid of choice at Ursuline Academy in Delaware, and I’m surprised to find that I still have a huge affinity for the pattern! Do I have any uniform twins out there?)
The unanimous 5-star reviews can’t be wrong, friends! Grab this little frock in deep raspberry, old forest (pictured here), or golden brandy (that color is only $49.50 right now, FYI!). I love how this tiered shape falls cleanly on all different types of bodies – shoutout to brands who show clothes on a variety of models!!! It’s about time!!! – but my favorite detail is the elastic around the wrist, which makes simple work of “rolling up your sleeves.”
Speaking of models with all different types of bodies: how incredible does the XL model look on the right?! This charcoal gray color is beautiful, but I REALLY love the camel version of this dress (and there’s a really pretty garnet, if red is more your thing). It’s a blank canvas that only looks expensive, you know? Dress it up! Dress it down! It’s the stylish equivalent of wearing a blanket outside during the winter. I LOVE.
Folks, we’ve got ourselves a twofer!!! This is actually a two-piece set – the cropped sweater can be removed and paired with anything else in your closet. (Might I suggest some on-trend high-rise flares, perhaps?) Worn together, though, it’s giving STRONG “ballerina off-duty” vibes, which is very charming. The black and navy feels very seasonally appropriate to me, but you can also grab this one in gray and white and monochromatic pink.
SORRY. Just one final milkmaid dress, I promise. (Some of us just can’t resist the siren song of a puffed sleeve and open neckline, you know?) I’m just so charmed by the khaki and black floral on the left – it feels like it belongs in the halls of a warm, custom, historic home. (Like, I want to wear this and then be transported into a Heidi Caillier home. That’s normal, right?)
If you’ve got Reformation taste on an Old Navy budget, THIS ONE’S FOR YOU. (And me. It’s for both of us.) Huge fan of this trending cut – the slit and neckline are so beautiful! – but love that it was done in a durable, practical, easy-to-care-for fabric. (And it’s from a sustainable brand, to boot!) This one’s almost sold out, so move quickly if it seems like it may be a fit for any of your upcoming winter soirees.
Highly recommend clicking through on this one – I LOVE how effortless this dress is when styled with a simple black pair of shades, chunky hoop earrings, and motorcycle boots. There’s something about the slouchy construction that’s just so cool, right?
I hope this one goes on sale soon because I WANT THIS TO BE MY NEW GO-TO LBD. A sweet rounded neckline? A body-skimming fit with a little extra room in the waist and hips? A pair of perfectly-tailored long sleeves, destined to hide my tattoos? A SCALLOPED SKIRT?! Pack it up, send me home, I AM DONE. I had a similar scalloped shift dress from J. Crew back in the day and I’ve always regretted parting with it as it’s been impossible to find an LBD that has the same level of charm…until now. (If anyone is feeling charitable, my birthday is on October 14th. You know, in case you want to send a gift my way.) (I kid. But hopefully, it goes on sale before then, you know?)
If you love the earlier look of a turtleneck but you prefer something a little more fitted (or with a little less fabric around your neck), this is a great option. I love the flirty, swingy skirt, but if you’re looking for something a little (read: a lot) more covered, they also make this style in an ultra-cozy maxi cut. Either will keep you both warm AND stylish this winter – it’s a win/win 🙂
Closing our roundup out with a dupe of one of Em’s most popular pieces! This Anthro dress is durable, comfortable, high-quality, top-rated…aaaaaaand, more than anything, it’s about HALF the price of Em’s go-to denim dress (pictured in the opening photo of this very post, if you need a refresher). But wait, it gets better: if this price is still a little too prohibitive, Target has also launched a $35 version! I do prefer the drape of Em’s and the wash of this Anthro piece, but man…that Target dress is a great way to get the look for a tenth of the price.
ALRIGHT, PALS. This is where I leave you (a mere 2,400 words later). Wanna chat about anything? I’ll be around, enjoying the fall breeze through my windows, waiting to hear from ya. See you in the comments. xx
Opening Image Credits: Photo by Kaitlin Green | From: 5 Flattering Dresses, 1 Cute Matching Set, And A Romper That’s Actually Comfortable: Emily’s Warm Weather Wardrobe Review
THIS POST WAS ORIGINALLY PUBLISHED HERE.
