While most of us in the States are still waiting for that first intoxicating fall breeze, it’s coming sooner than we think. So it’s that awkward time when we no longer want to invest in “summer clothes” but also don’t want to buy something and wait a month or two to wear our cute new picks. We all know the answer though don’t we?? IT’S A DRESS. But not just any dress. This dress needs to be versatile and take us from now through the fall (and ideally beyond). Extra points if you can easily layer with tights and a coat. And that’s what we have for you today, 29 dresses that still feel fun enough for the end of summer but will easily transition into the cooler months. Oh, and all but two are under $150 and many are under $100. It’s a party!
Denim
Short-Sleeve Jean Shirt Dress | Oversized Mini Shirtdress
I wanted to start with a classic and a style that is synonymous with Emily Henderson and EHD as a whole…The short denim dress! She’s been wearing them for years for a reason. They are maybe the most versatile type of dress because look casual but like you still tried. For the summer, they are great with a cute flat but come the fall, they look SO cute with leggings and tall boots. Heck, you can even throw a long-sleeved top under if you want. You really can’t lose here.
Now for these picks above. On the left, I chose this very fun and sweet $45 cutie with a slight puff sleeve that I love. Since it’s from Old Navy the sizing goes up to 4x and has three different length options. THANK YOU OLD NAVY! For the dress on the right, I really love the wash of that denim but it’s Madewell so no surprise there. The stitching on this one is also just so good and I love the shape of the pocket flaps (?) Very classic. This one also comes in a light wash but this one feels more “year-round” to me.
Jean Popover Shirt Dress | Denim Tee Shift Dress
If a full-on button-down dress isn’t your vibe then this adorable and very cool quarter button-down may be perfect! It’s only $50 (I KNOW!) and also from Old Navy with all of their sizing options. And let’s not forget to mention those great pockets and the fact that the sleeves are long for extra warmth in colder months. But an added striped long-sleeved turtle neck would look pretty cute and make it even cozier. Then the dress on the right is from Abercrombie and if you saw our try-on post you know that Caitlin and Mal loved their sleeveless version. But this very chic version comes in two other colors and three different lengths. So don’t stress if you love it but think it might be too short!
Striped Loose Shirtdress
The Linen Daytripper Shirtdress | Loose Mini Shirt Dress
For a similar vibe to the dresses above, but in lighter/slightly more warm weather-friendly fabrics, are these cotton shirt dresses. As a team of stripe lovers, I thought these two could use their own special category:) But both of them also come in other solid colors that might be better for fall if you prefer. I just loved how cool and simple the cuts/details of these were. And as the hot summer sun cools down these would look great with a jean or a leather jacket paired with some booties.
Elevated Shirtdress
100% Organic Cotton Gauze Split Neck Midi Dress | Button-Front Mini Shirtdress
While almost all of the dresses in this post have a throw-on-and-go aesthetic, this section in particular really embodies it. Look at the blue dress on the left. It’s got a cool sleeve length, a nice little V-neckline, and is beautifully tiered. It’s just easy to wear in so many different situations. Another perfect one for flats in the summer and cute boots for colder weather. You will look great for under $60! But I also love the effortless coolness of the olive green dress. This is a great dress for right now (end of summer) but once it cools down a little, layering a patterned long-sleeve shirt or just rolling down the dress’s sleeves will be perfect. I also think that loose waistline is a great way to call attention to your waist without any constriction. THE DREAM.
But also let’s not forget to have fun with pattern! We are so used to busting out the fun florals, etc for spring and summer but they deserve to be out all year long. This patterned shirtdress is still loose but has great details to not make it feel too unstructured. We are newish to Boden but boy are we fans. This dress is not only under $100 the sizing is way more inclusive than most.
Structured Shirt Dress
The Frolic Dress | Eyelet Mini Shirtdress
For a more structured look, these two are ELEGANT. The shapes are playful but the fabrics are super relaxed. These are also great for the office (you’d just have to make sure the eyelet dress was a good length for your job). Otherwise, these are great options for places and events where you don’t want to be dressy but you do want to look nice.
Oversized Chic
Oversized Open-Collar Shirt Dress | Fitted Short-Sleeve Mini Dress
I know these two won’t be everyone’s cup of tea but I LOVE them. They feel so cool and more oversized/architectural than most. The dress on the left has less shape (but does have pockets!) and the dress on the right is a bit more fitted if that’s more your style. They are styled for warm weather in these shots but I’m telling you, black tights and over-the-knee boots topped off with an oversized coat, no one is going to look chicer than you.
Not Your Average Shirtdress
Flora Cord Shirt Dress | Cinched Zip-Up Dress
There seems to be a pretty wide definition for what a shirtdress is but if that green corduroy is one then SIGN ME UP! It’s another beauty from Boden and that color is maybe perfect. I also happen to love corduroy. It’s fall time gold that could also be worn at the tail end of summer as long as it’s not too hot:) As for the black dress on the right, I like how it feels both casual and kinda edgy? I mean that zipper is very cool and makes it feel unique. Plus it’s from J. Crew so you know the quality to great!
Structured Maxi Sleeveless
The Linen Belted Midi Dress | Denim Maxi Dress
Wow, I love this silhouette! The lines are stunning and that high-neck + sleeveless look just screams “I don’t care about trends, I just know what looks good.” The tan number on the left is one of the picks that is a little over $150. But at $168, it’s 100& linen, has a pocket, is fully lined, and has that great belt. Add heeled boots and a trench coat an it’s a perfect outfit. The black one is actually denim which I think makes it even cooler! The cut definitely looks formal but the denim really makes it more casual. Oh, plus the denim has a stretch and it’s under $100. Win-win!
Cool Lines
The Muscle Tee Midi Dress | Bronte Ottoman Dress
Would this be an EHD fashion post if we didn’t have a lot of stripe options? I didn’t think so:) Stripes are timeless, are great year-round, and these two dresses are both of those things. Now, if you know me you know my love of my shoulder-padded t-shirts is almost too deep to talk about. I wear all three of them every week (and have for at least three years). This is all to say that while this black and white dress’s shoulders aren’t padded, I love the slightly exaggerated muscle tee look! This is just a cool gal-vibe dress that truly could be accessorized with nearly any style. The other dress on the right really caught my eye because of that color combo! Who doesn’t love ochre and navy together?? We sure do. Plus, the silhouette is so pretty and it comes in four other colors.
Gobsmocked!
Smocked Midi Dress | Fit & Flare Midi Dress
It’s now time to get a little whimsical. A smock dress is another classic we all love too. This deep wine color on the left dress is to die for. Definitely more “fall” than “summer” but also who cares! It’s beautiful, has so many pretty details, and is a good price at $88. Then for our long-sleeved beauty, you get a bit more coverage, if that’s your preference, and pockets! And that one is under $55. While nearly all of the dresses I’m about to talk about fall into this category, these two are great options for Thanksgiving dresses if you are into thinking that far ahead:)
Whimsically Earthy
Waist-Defined Midi Dress | Puff-Sleeve Mini Dress
I truly fell in love with these colors as much as I did with the shapes. The dress on the left is still in the smocked category with that great waist definier but those sleeves are also a showstopper. If I’m honest this dress definitely reminds me of Ulla Johnson but for a fraction of the price at $50. Old Navy is coming through with the style, sizing, and prices. But if you prefer something a little less detailed and fitted this dress on the right is perfect for you. The rich color, the awesome puff sleeves, and the tiered look have me absolutely sold. And see? Great Thanksgiving dress options.
Neutral AND Fun
V-Neck Balloon-Sleeve Maxi Dress | Tiered Maxi Shirtdress
You may or may not have guessed that the dress on the right is the other dress that is slightly above the $150 mark (but only by $8!). But look at it. How could I have not included it?! The shape of it might be my other favorite and I love that it’s a print that isn’t a floral (not shade to florals, just nice to have other options). No notes and I think it’s a perfect option for all year long. Then the dress on the right is an awesome floral dress that’s still in the neutral-toned world but a little moodier. I think that’s a perfect vibe for the last part of the year and/or if you aren’t a bold color person. Also, great sleeves and a sweet little detail between each tier.
Pattern Play
Fit & Flare Long-Sleeve Mini Dress | Emma Long Sleeve Jersey Dress
Speaking of patterns, look these these stunners! Small-scale patterns with modest necklines, and fitted bodices. I’m in. Plus, you don’t even have to ask yourself “What bra am I going to wear with this??” because you can wear whichever one you want! Since these are both long-sleeved, they aren’t going to be as versatile with those lingering hot days of summer. But hey, maybe you work in a really cold office so some sleeves are welcome:)
Last but not least is this fun and elegant beauty. This one is going to show a little more cleavage (unless you add a tank top of some kind under). But I love that it’s long, there’s a pretty detail at the shoulders, and it has a very fun bold print. The colors are so pretty too! Oh, and it goes up to a size 20/22 and comes in three different lengths. It’s a slam dunk which is how I like to end every post:)
What do you think? Any favorites? Any reviews if you own one of these dresses? Let’s chat!
Love you, mean it.
Opening Image Credits: Photos by Kaitlin Green | Left From: Really Good Denim (+ The Non-Skinny Jeans That I Like Including My New Favorite Barrel-Shape) | Right From: Is It Time For “Family-Friendly” (LOL) Cute Spring Dresses?
THIS POST WAS ORIGINALLY PUBLISHED HERE.
