The Ultimate wool& Dress Guide NEW & UPDATED

My first wool& Dress Guide has received a ton of views so I am here to update it with some of the newer dresses I have tried since!

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Click here to check out the whole selection from wool& (wooland) Merino Wool dresses.  There are also pants, shirts, PJs, and cardigans! So much to love and the most fantastic way to build a truly sustainable, truly functional, truly beautiful capsule wardrobe. 

If you are trying to decide which dress is for you, you aren’t alone. It’s definitely a hard call since you can’t try them all on in the store. (Unless you are lucky enough to live near their HQ). And if you are planning on completing the 100 day challenge, you will want a dress that fits great, is versatile, and makes you feel like yourself, right? These are investment pieces so they aren’t cheap….. and sizing can be a bit tricky, but remember, you are building a sustainable wardrobe and finding a dress that will last you a long time. So taking a little extra time to choose it, isn’t so crazy in my book.

I will tell you that I am getting more wear out of my wool& dresses than I have any other dresses in years, and that’s saying a lot because I have always been a fan of dresses, even as a child. I keep hearing that women who don’t typically wear dresses, are converting to them when they find wool&, so it’s really quite the phenomena!

Are you ready for a super photo-heavy post? Here we go:

My Stats
Because I know people can benefit from size, measurement, weight stats, I’m sharing my details even though I don’t love my current weight. I’m currently 5’6″, and about 175 lbs. In my skinny-state, I’m a rectangle shape, but when I am over-weight, I’m more in the pear category, carrying my weight in my stomach and thighs.

The Penny
I  have been curious about the Penny since I first saw it. I’m a person who in the past relentlessly tried different versions of denim dresses, skirts, and jackets because I was always looking for the perfect ones. The perfect denim pieces are hard to find! After trying the Penny (and the Greta), I am in love with the fit, fabric, and finishing details of both. They are beautifully made and the wrap style is excellent, even on my less than hourglass self. I got it in a Large and I am quite happy with the fit.

I love the wool& Penny so much and it has absolutely exceeded my expectations. The material is soft but structured and the fit is absolutely perfect and customizable with the sash.  I worried it would flare out too much and not be quite as trim as I liked, but it isn’t an issue at all. I love the way it fits and feel like it’s super flattering and gives me that hourglass shape! I was also concerned it would look too big for me at the shoulders because in a size large but it really doesn’t at all. The wrap style lets you basically customize your fit. I find the dress to be adjustable enough for modesty and also comfortable to wear while sitting with minimal gapping. I absolutely love the fit of this dress and I feel very put together and confident when wearing it! For more info on the Penny, check out my wool& Spring Haul post!

  • Pros: The professional cut and denim fabric blended with wool make this dress such a stand-out!
  • Cons: The only thing to note is that the sleeves do not push up very far, which is kind of a downside for those of us who love to push them up! Also, take note of the fabric break down, there is less wool in this dress!
  • Favorite Look: As shown above, worn as designed with a statement necklace and wedge sandals!
  • Fabric: 69% cotton, 31% merino wool denim

The Norah

The wool& Norah is so beautiful and I love the styling that is unique and eye-catching. I have always loved dramatic sleeves of any kind and the batwing style of this dress gives a little extra “something” and I find it very flattering! For size, I went with medium since the waist seemed to hit a little bit higher and it looked pretty flowy in the bottom. It’s definitely not clingy and has relaxed a bit as I’ve worn it. I think this size is perfect. I love where the waist hits me, the loose sleeves are really flattering and I think it really balances out my not-hourglass figure.
The seaming in the front gives lovely shape and the length hits me at mid calf.  One thing to note is the sleeves look a bit long on me but I do have short arms. (My grandmother said that every time she made me a dress). They are almost bracelet length on me, which I don’t mind. I like the look of the dress with the arms pushed up slightly, anyway.
I will probably wear it forward the most, but I do think the neckline is very elegant backwards, I really like it with the necklace. The back is pretty with the V-swoop. The cobalt is a little “softer” in color than I expected, but it’s very pretty! As always the dress is crazy comfy and I love this soft Cobalt color.

  • Pros: The design for this dress is so much fun, I especially love the seaming on the front and the elegant batwing sleeves. The length is also perfect and the color options are both really gorgeous. I would also love to see this in Marionberry, I think it would be so beautiful. Another pro is that this dress is truly reversible and actually looks good both ways!
  • Cons: Nothing comes to mind as a con for this dress, but I do think the sleeves might be a bit of an acquired taste in fashion. I love sleeving details (like I’ve said before) but it’s not always everyone’s cup of tea.
  • Favorite Look: I will be trying this one many ways once Fall rolls around, but for now, my favorite way is actually backwards with the necklace! I think it gives a really beautiful style option and the back is just the right dramatic cut without being too low!
  • Fabric: 78% Ultrasoft Merino Wool, 22% Nylon

The Milena

I had my concerns about wool& Milena, mostly because I wasn’t sure if the more straight cut would be good for me (I am also rather a straight cut myself or a rectangle shape morphing into a pear as I have gained more weight!). I decided to go with a Large in Milena to make sure it wasn’t too tight and I am glad I did!

It turns out, I’m obsessed with this dress and I keep grabbing it again and again! I love the vneck, the length is perfect and this is actually one of the most easy-to-layer dresses I’ve ever owned.  It actually looks good with shirts over or under it and it layers perfectly with the Greta skirt over it. It’s cool in the summer but the length will take me right into fall. I also love grey as a casual neutral and feel like this particular Charcoal Grey is such a sophisticated shade! Check out more details and photos in my wool& Spring Haul post!

  • Pros: I think the design itself is really perfect, particularly the length, slitted hem and v-neck cut. It turns out I really love the straighter cut to the skirt.
  • Cons: I guess my only con is that there is a little bit of relaxing around the arms after several wears. It’s not as much as some of the other styles, though.
  • Favorite Look: I love it with this Julahas Belt and wedge sandals, but I also really love it layered with the wool& Greta skirt over it!
  • Fabric: 78% Ultrasoft Merino Wool, 22% Nylon
    180gsm, 17.5 Micron Wool

The Sierra
The wool& Sierra
is one of the most popular dresses that wool& makes, and when you try it you will understand why. The thicker fabric is super forgiving, glides right over any problem areas and is just as comfy as your favorite sweatpants. It’s versatile tank styling is idea for layering both over and under and the thicker fabric means it’s even more sturdy than you’d expect.

I actually didn’t love Sierra from the first moment. Once I tried layering, however, I became a huge fan. And now I’ve been wearing it alone and definitely have come to appreciate it! Sierra is one that most people size down for, going by bust size as the best guide for a good fit. I wear a size small and my black Sierra is regular length. I just bought a Forest Night Sierra in size small long, which gives a little more length for wearing solo. I find that I like shorter dresses for layering, and longer dresses for wearing alone.

  • Pros: The thicker fabric is absolutely fantastic. Comfy, soft, and crazy forgiving. In fact, the shirt above is actually very thick and ruffly but the plush fabric of Sierra totally hides it making layering so easy! Wearing Sierra as a jumper is actually my favorite way.
  • Cons: My only con for Sierra is probably that it does feel a little hot in the humidity of a South Carolina summer. I know lots of Woollies who wear Sierra all year round but when we have a record high day, it’s not the one I will grab (I would probably grab Camellia, instead.)
  • Favorite Look: Layering gives Sierra so many fantastic looks, it’s hard to pic just one. I especially loved it layered over floral, like I shared in this blog post.
  • Fabric: 75% Ultrasoft Merino Wool, 22% Nylon, 3% Spandex

The Charlie Jumpsuit
Is it correct to put the Jumpsuit in a post about dresses? I guess we could debate it, but I decided to include it because it’s the comfort of pants plus the ease of a one-piece which makes it wonderful and comfy. I wore the Charlie Jumpsuit this week for my 20th anniversary. It was a crazy busy week and so we went out for a casual dinner at a hole-in-the-wall Indian restaurant and then grabbed some delicious dessert at a riverside restaurant. I put on the Charlie Jumpsuit because I wasn’t sure where we’d be going but I knew it could pull off casual and dressy so very easily, plus I would be so comfortable at the same time!

I could not wait to try the Charlie Tank Jumpsuit from Wool&. I knew the moment I heard that there was a Jumpsuit coming that it would be a winner. One piece simplicity, the incredible benefits of wool, plus Wool& signature soft easy-care blend? I was totally all-in and went with a size Large, which has been perfect.

  • Pros: One piece construction, soft, comfy fabric and flattering cut.
  • Cons: I have heard a lot of people don’t love the length of this jumpsuit. I think it’s so hard to fit people correctly but I honestly love the length and the fit of this for me. I will say, the arm holes do droop a little for me (probably because my top half is smaller than a large). I was going to have it altered but now I just wear a black bra and hope for the best.
  • Favorite Look: I love it with Julahas capes and Kimonos! It’s so easy to dress up this way, and yet you still feel like you are wearing pajamas. Shown above with Julahas Daria Ganges cape. Remember you can save 10% on Julahas with this code: LEAH.
  • Fabric: 78% Ultrasoft Merino Wool, 22% Nylon
    160gsm, 17.5 Micron Wool

The Willow
I don’t know why Willow initially did not appeal to me because I wore it approximately a zillion times this fall and winter. I love the 3/4 sleeves because they seem to really hit me perfectly, love the vneck and I love the looseness. This dress seems a little shorter than others which I initially was concerned about. Then I realized that I actually much prefer shorter dresses when I am wearing them with leggings. The Willow became my go-to layering option through the fall and winter months.

Here’s an example of how I wore Willow all winter, with leggings, boots, a long necklace and one of my Julahas capes (this one is Daria Danube).
  • Pros: For me, Willow is the perfect blank canvas, 3/4 sleeves and the vneck style is very flattering!
  • Cons: For me the length is too short to wear as a dress alone but I love the length as is for layering, so I’m not mad about it!
  • Favorite Look: Willow + Leggings + Julahas Cape
  • Fabric: 78% Ultrasoft Merino Wool, 22% Nylon
    160gsm, 17.5 Micron Wool

The Rowena
The Rowena is the Original 100 Day dress. It’s a beautiful, classic swing dress and still one of the most popular wool& designs. At one point I tried a Small and the arms were a bit too tight for me. I decided I wanted a loose and swingy silhouette and went with a size Large. I love the way this dress fits me even though it’s on the big side. (the Pine color and Marine Blue Rowenas below are size Medium). Bonus: it has pockets and is currently available in regular or long lengths, plus the choice of 18 different colors!

  • Pros: I love the clean lines and simple design of the Rowena (or Ro, as wool& fans call it). It’s so comfortable and looks amazing with leggings and boots.  This dress is a blank slate for winter layers!
  • Cons: This isn’t really a con but I tend to avoid long sleeves because I get hot. Since wool is temperature regulating, though, it’s still great for me. In this photo, I’ve pushed up the sleeves, which is the norm for me!
  • Favorite Look: Rowena+Leggings + boots. In this photo, I’m wearing it with my Sash Bag, suede boots from forever ago (similar here), and a thrifted leaf necklace(similar here).
  • Fabric: 78% Ultrasoft Merino Wool, 22% Nylon 160gsm, 17.5 Micron Wool
    Wool& Rowena in Pine shown here with Julahas Celestial Neptune Cape

    wool& Marine Blue Rowena worn here with Julahas Celestial Neptune and Julahas Danube

The Brooklyn
This faux wrap dress was one I originally avoided. I felt quite sure that it wouldn’t work for me with my pear-shaped body and smaller chest. I was so wrong and I actually adore my Brooklyn dress now that I’ve tried it. (I should confess, I own it in two colors). It’s an elegant, feminine look and it even has a reversible design. I wear a small in Brooklyn. I have also tried a medium and it’s a little too loose. This popular dress is now available in long as well.

  • Pros: I love the looser top. comfy elastic waist, and reversible style. The dolman-ish sleeves are so flattering and perfect for those of us who aren’t feeling fab about our upper arms.  This dress would be the perfect breastfeeding dress, also. For me, it’s a date night dress!
  • Cons: The faux wrap is a bit loose for me, and sometimes shows a little too much. Could be solved by a couple of stitches but I haven’t bothered pulling out the needle and thread. A tank top underneath also solves the problem. Some people really miss that there aren’t pockets in this dress, but I don’t mind at all.
  • Favorite Look: Black Brooklyn with a statement necklace and ballet flats. In this photo I’m wearing my Marine Blue Brooklyn with olive green Allbirds flats and an olive cardigan (similar here) from Stitch Fix. 
  • Fabric: 78% Ultrasoft Merino Wool, 22% Nylon
    180gsm, 17.5 Micron Wool

The Camellia
The Camellia is a more flowy, lighter-weight tank dress and is super soft. For my intense summers, I prefer the Camellia’s weight to Sierra but it’s just personal preference. For more details on this dress, check out my original post.  A lot of people ask the differences in Sierra and Camellia. The Sierra has patch pockets, a wider skirt, and a more substantial fabric. Although I love Camellia’s flowy style, that does make the fabric a little more delicate and therefore it’s a smidge less sturdy than Sierra. I feel I have to be a bit more careful with Camellia. Like many of the other styles, Camellia is a generous size, and I wear a small long. For the swing styles, it’s easiest to decide your size based on your shoulders and bust.

  • Pros: Lightweight, flowy, and pockets! Easy to layer, works well for all seasons (at least in my warm climate).
  • Cons: The fabric is a little more delicate.  (The fabric breakdown shows the differences in thickness between all the dresses).
  • Favorite Look: I love my black camellia layered with a light, summer kimono and birkenstocks. In this photo I’m wearing with Birkenstocks and a salt and pepper hat from a local boutique (similar style here).
  • Fabric: 78% Ultrasoft Merino Wool, 22% Nylon
    160gsm, 17.5 Micron Wool

The Maggie
I suspected I would love the Maggie because it’s cut very much like the Stella Tee (and I was correct). This swing dress is a perfect base for accessories and just a nice all around basic to have in your wardrobe. The cut is a little slimmer than some of the other styles and it has pockets plus the scoop neck is very flattering. As I’ve gained a good bit of weight (thanks, Zoloft) I am gravitating more to sleeved styles rather than sleeveless ones. The Maggie is a generous size; I currently own a Small Long  and I love it but the medium also works for me (this Marionberry Maggie in the photo is a Medium). One thing to note about Wool& dresses is that you should check the size chart to decide on lengths. I don’t consider myself tall, but I often prefer the long lengths.

  • Pros: This dress has pockets and is a blank slate for layers and accessories. A slimmer cut than the swing dresses , so less fabric and very lightweight.
  • Cons: Some women don’t like that the pockets may add a smidge of bulk to the hipline. My black Maggie dress has actually had the pockets removed!
  • Favorite Look: I just love this dress by itself, but I also love to add on one of my Julahas Kimonos. This one is Julahas Jiva Wool Silk Kimono Fire and it’s so gorgeous.
  • Fabric: 78% Ultrasoft Merino Wool, 22% Nylon
    160gsm, 17.5 Micron Wool

The Renata
The Renata  is my dressiest Wool& dress! I have always loved bell sleeves and these are the perfect length and size to stay out of the way but still add a little extra drama to the silhouette. The fit and flare cut is really flattering , rides easily over my problem areas, and the waist and sleeves add some structure. Plus, pockets! I can’t wait to wear this dress to dinner or parties. I think it would be the perfect holiday dress as well and I’m really excited that they also released it in Marionberry which is a gorgeous purple.

  • Pros: A dressier option, Renata gives a little more structure with a nice a-line classic design. The pockets are beautifully hidden within the seam and don’t add bulk,  but are totally handy. I love the bell sleeves. They aren’t crazy dramatic or too bulky to fit under a jacket or coat. They also aren’t long enough to get in the way.
  • Cons: I can’t really think of any with this dress! Because it’s dressier, I would love to see it in a slightly heavier fabric (more like the Kalle to give it a little structure) but I honestly have zero complaints. I love the look, feel, design and everything about Renata!
  • Favorite Look: In this photo, I’m wearing it with Vionic Sandals and a statement necklace from Baublebar (similar here). It would have looked better with heels but I’m really a flats girl!
  • Fabric: 78% Ultrasoft Merino Wool, 22% Nylon
    160gsm, 17.5 Micron Wool

The Summer Midi
At first, I wasn’t sure this was the style for me, but I wanted a slightly longer skirt so I gave it a try. It turned out I love the Summer Midi and for me it’s the perfect versatile summer dress. I love the length, love the vneck, and for the first time in my life, I love the sash. I think because I am long waisted, I don’t like the way some belts hit, but because there are no loops, I can wear this sash exactly where I want. And it stays, feels comfy, and doesn’t get loose or slide down! For me this is the perfect LBD for any occasion. This dress is also reversible, and can be worn without the belt for another look making it a really versatile piece. I wear a medium in the Summer Midi.

  • Pros: Versatility for sure! With the reversible design, the removable sash, and the midi length, this dress can work for almost any occasion. I’ve seen it layered in so many ways, also. It brings a ton of options to the table.
  • Cons: I don’t love the pockets on this dress as much as the inseam pockets from some of the others. They are designed to work both ways for the reversible function, so it makes sense that they are designed like this, but I would just as soon have no pockets.
  • Favorite Look: I’ve mostly just worn this dress alone with the sash for church. It looks very sophisticated! In this pic, I’m wearing it backwards with the higher neckline in front, black Fitflop flats, and a Kendra Scott Rayne necklace. I feel like I could do anything and go anywhere in this outfit.
  • Fabric: 78% Ultrasoft Merino Wool, 22% Nylon
    160gsm, 17.5 Micron Wool

Amalya Button-Front Dress
The Amalya is a little bit retro and perfectly office appropriate.  As you can see in the link, the dress can also be worn open like a cardigan. It’s a little longer than some of the others at knee length and I adore the dolman sleeves. Like most of the Wool& designs, the features are subtle so they enhance without being distracting or dramatic. The blousing affect from the fitted waist and looser sleeves is very flattering and gives me the illusion of an hourglass figure. (I very much do not have one). I am absolutely dying to try this dress with a belt.  For this style, I sized up to a large. The medium fit, but it was a little snug in the muffin-top area.

  • Pros: I’m loving the looser, longer sleeves, the waistline and the fun button details of this dress. The inseam pockets are pocket perfection. I feel like June Cleaver, in the best possible way.
  • Cons: Ok, I’m going to be a little nit-picky here and say that I wasn’t thrilled with the workmanship on the buttons of this dress. They just look a little messy and not as nice as I expected for the price. However, that’s not going to affect my enjoyment of this dress one bit and if they need re-stitching I’m perfectly capable. I love it so much.
  • Favorite Look: I think this dress is going to be quite a chameleon in my wardrobe. I wore it this weekend downtown with my olive geen Allbirds and a pair of sunglasses and I honestly felt very chic. We were shopping lots of homemade vendors and vintage shops and I felt like I really fit the vibe for a change!
  • Fabric: 78% Ultrasoft Merino Wool, 22% Nylon
    160gsm, 17.5 Micron Wool

Audrey Maxi Dress
Audrey is the first maxi dress from Wool& and it is perfect. I love the cut, length, and soft feel, plus I am obsessed with this color, Black Heather. It’s basically everything I love about black with a little less visible lint. My husband says this dress is his favorite.  Pockets, side slit, flattering cut. I’m wearing Audrey in a small!

  • Pros: My pros and cons are almost the same which may sound weird. I love that this dress isn’t floor length. Many maxi dresses are way too long to comfortably wear. At 5’6″ this is perfect. Petite ladies may need to have this dress altered since it is generous in sizing.
  • Cons: I know some customers want a long version of this dress. I hope they offer one soon, because tall women like maxi dreses, too.
  • Favorite Look: I enjoyed wearing this dress with a  lightweight cardigan from Lularoe but I also love it as a standalone outfit.
  • Fabric: 49% Ultrasoft Merino Wool, 33% Tencel™ Lyocell, 18% Nylon 200gsm, 17.5 Micron Wool

Fiona Fit & Flare
The Fiona Fit & Flare is a great basic for your wardrobe and I’m sorry that is no longer available in this slate blue, which is a beautiful blue-grey. I feel like 3/4 length sleeves are so flattering and this waistline is comfortable and cute. This dress is a great Fall option, perfect for layering.

  • Pros:  3/4 sleeves, a little extra length, and comfy waistband.
  • Cons: Because this dress is a little more conservative I think it runs the risk of being a little frumpy.
  • Favorite Look: I will be wearing this dress with scarves and leggings for a Fall look. In this photo, I’m wearing it with Fitflop flats and a Lululemon Vinyasa scarf.
  • Fabric: 78% Ultrasoft Merino Wool, 22% Nylon
    160gsm, 17.5 Micron Wool

Kalle Ponte Tank Dress
Even though I didn’t keep it, I absolutely adore the Kalle Ponte Tank Dress. It’s a structured, but still comfortable tank dress that would be perfect for a business wardrobe. If you have to travel for business, this dress could be the ideal solution. I think if I had worn some shapewear under this dress, it would have flattered me better. Between my weight gain and the fact that I don’t often go into the office, I decided I would pass along this dress. If I ever lose this extra weight, or end up back in the office, I’ll be back in line to buy Kalle.

The Cora
The Cora is a classic with a little bit of a retro spin. There has been a ton of excitement surrounding this dress because it comes in this awesome navy stripe and everyone loves the versatility of the included sash. This dress is also a little longer than most, which makes it perfect for taller ladies or a business casual environment. I tried the navy strip and it is incredibly cute. Ultimately, I did not hang onto this dress, but if I worked in an office, I think I would have kept it.

Tulip Tank Dress
The Tulip is a very body-con tank dress that looks so great on the right body type. If you want a comfortable dress that hugs the curves, the Tulip Tank Dress is a winner. I’m definitely not comfortable in this style but if you are looking for something very fitted and a little more vava-voom, you’ve got it here! This dress also comes in ocean teal blue which is absolutely beautiful. I’ve seen a lot of different body types pull this one off!

Ellie Midi Dress
I tried the Ellie Midi dress and think it’s amazing, especially as a nursing-friendly option. I didn’t find it as flattering as some of the other styles for my body type so I didn’t hang on to it. The tie style does give you some control over the fit, which is nice. I really love the Pine color. It would make the perfect holiday dress.

Dresses I Haven’t Tried (Yet)

Looking for more Wool love? Check out these other posts:
How to Save Money on Wool& Dresses
Woolx Joggers Mini Review & Coupon Code
Wool& Camellia and Axis Cropped Leggings Review
Wool& Mara Honest Review
Building a Sustainable Wardrobe

Ready to being your love affair with wool? Let me know what your first purchase is going to be!