Leah’s off to a wedding this weekend, and the timing is perfect because I wore my Bitter Lollipop Riley dress for the first time yesterday and want to tell you all about it. I’ve been eyeing this dress ever since Kelly Roberts launched her brand last year. She’s had a lot of sales since then, but this dress was never part of them.

Now it’s September, and with our 4th Annual Big Bust Clothing Swap coming in just a week, this is the month for cleaning out our closets and identifying essentials. I contacted Kelly to see if she’d like me to review the Riley and Paige dresses in connection with this theme, and she agreed to send me one of each. I’ll write more about the Paige later (spoiler: it’s as flattering and versatile as I thought it would be from the pics), but today is all about the Riley.

I don’t know why I gravitated to the Riley so much. After Kelly agreed to send it to me, I was hit with remorse–why had I asked for something black and white and angular? I look better in spring colors, and my curly hair is the antithesis of all straight lines. But when I took it out of the box on Wednesday, I knew my instincts were justified.

This is a simple dress with clean lines and an interesting pattern that can be dressed up or down. I wore it both ways yesterday. Here’s how I wore it running around Manhattan during the day.

bitter lollipop casual riley front

Here’s how I wore it to the open house for Bottomless Closet volunteers later that evening. I simply added a necklace and changed my shoes in the elevator. It was a well-dressed crowd, and I fit right in.

bitter lollipop dressed up riley front

Throughout the day I glanced at my profile in store windows and admired my streamlined look. (Yes, that’s bagging you see over my shoulder blades. It’s a common issue for me, but not everyone runs into it.)

bitter lollipop casual riley side

It was probably our last really warm day of the year–the temperature reached 89 degrees. The lining is 96% cotton, and although the dress is very fitted, it never felt clingy or hot. Besides being extremely comfortable and helping to keep everything smooth, I was also impressed that the lining is hemmed with the rest of the dress. I’m used to pulling a tight dress like this down my hips and having to shimmy to get the lining to catch up, but in this dress the shell and the lining are a single unit.

bitter lollipop riley hemmed lining

The lining is probably one reason this dress seems to have a life of its own–the structure carries the shape of its wearer even on the hanger! However, the fabric isn’t stiff at all.

My waist currently measures 31″ and my bust 39″, so Kelly put me in size 14Busty, which is perfect. This picture shows you how much room there is for the bust without it being stretched out.

bitter lollipop riley life of its ownThe next picture is meant to show you that someone with a much larger bust could still fit into this dress with only a little stretching.

bitter lollipop extra space 14busty riley

This dress is going to be a closet staple for me. I’m actually wearing it again today! (This means I’ll be washing my new dress this weekend. Kelly says the fabric has been pre-washed, so I don’t expect any shrinkage, but I’ll update here if I run into any.) I’m looking forward to figuring out more ways to accessorize it, and with its sturdy fabric and seasonless print, I’m going to look for ways to layer it for cooler weather.

I’m sorry to report that the Riley is now sold out. I asked Kelly if she plans to offer variations of this style because I love sheaths (she calls them shifts). She said that there will be more in the future, but she doesn’t have any planned right now. The fit & flare and midi dresses have been a lot more popular, so she is focusing on doing variations on those. If you love sheaths (or shifts?!) like I do, then you might want to snatch up the Kate while you can! It’s the one similar style currently available, and it also comes in a seasonless, versatile print.

And if you’re now a Bitter Lollipop fan like I am and live in or near New York City, then clean out your closet and come to our clothing swap where you’ll have a chance to win a dress from Kelly’s newest collection!


I did run into an interesting issue with the neckline yesterday that I’m going to describe below: there seems to be a lot of extra fabric above my shoulders. No one else has complained about it, however, and Kelly is going to look into it.  [Interestingly, there is NOT a lot of fabric for the width of the shoulders–shoulder point to shoulder point measures only 12.75″. Most women I’ve measured have had a shoulder span of around 16″, and I’m pretty average. I think that the wide neckline and stretch fabric kept the shoulders from feeling restrictive.]

wpid-bitter-lollipop-riley-extra-fabric-demo.jpg.jpegI thought it would be a simple matter of smoothing the neckline down, but I ran into issues when I wore my shoulder bag. Perhaps someone much bustier would fill out more of what is empty space on me.


My temporary fix was to fold the extra fabric over and hold it in place with the straps of my bags! Any ideas for what I should do for a permanent fix?


If I have to stop using a shoulder bag in order to keep wearing this dress, then so be it because I love the Riley. The neckline is extremely flattering because it hits my lower balance point (more on balance points here). This means it would probably require a cami in a conservative office, and anyone standing over me while I sat on the subway yesterday certainly had a clear view of my tacking gore center.