Assignment from Shana to Linzi: 

Linz…we just received the nicest e-mail from a reader, let’s call her V, wanting advice on how to accessorize an Eileen Fisher black dress for a business casual evening event…let’s do this!”

The E-mail 

Subject: Big Fan Needs Outfit Help
Message Body: Hi The Mom Edit!  I’ve been following your site for the past year and a half and just love it…Next weekend my husband and I are heading to his ten year dental school reunion…. The dress is business casual and the event consists of cocktails, dinner, and dancing. I’d like to look good. Below I linked the dress and shoes I bought from the Nordstrom anniversary sale…I was planning on wearing both but, would so appreciate some styling advice. Do you like the shoes with the dress? Do you think it is indeed business casual/ more importantly stylish? What accessories, colors etc do you suggest? I’m a pretty neutral, comfy, kind of girl. Hence, I always buy Eileen Fisher and I’m 34.  I would just love to hear your thoughts. Thanks in advance for your help. I can’t wait to hear from you. Take good care.
Your biggest fan,

Our Thoughts

V, we are so excited about your upcoming weekend with your husband, and we are honored to help you put something together that makes you feel great. Shana and I teamed up on this one (to try and strike a balance between practicality and style), so I hope you like what we came up with.

Your Goals: Look Stylish, Look Good, Look Appropriate for Business Casual, Be Comfy

The Dress: Well done on your choice of dress. I love Eileen Fisher. She makes fantastic high-quality pieces that fit well, drape nicely, and are easily accessorized because of their clean lines. They are also pieces that will be in your closet forever. Since the attire suggests “business casual”, the dress you chose is ideal….not too much skin and a conservative cut. Most Eileen Fisher dresses are great for business-appropriate events and are super-versatile. Classy choice  — way to go, V, on a great selection!

The Problem

The Eileen Fisher dress is a classic cut (that is comfortable to wear) and has well-designed bell sleeves, but both Shana and I think it needs some “oomph” and a bit of “fancying up” for a special event like this (especially since it’s in the evening and involves cocktails and dancing). Luckily, that’s the beauty of Eileen Fisher dresses…they are so versatile that with the addition of just a few accessories, this is an easy problem to solve.

The Solution

The Shoes: You asked if we thought the Eileen Fisher stacked heels you have would work with the dress. Shana thinks you need to go sexier…way sexier. She says the shoes are absolutely fabulous, but not quite right for this evening occasion with this dress. For true “business casual”, though, I usually say closed-toe shoes. I think you could wear your Eileen Fishers (if they are comfortable and you feel great in them, go for it!), but the thing about a reunion is even though they say “business casual”, we all know there will be folks who are way more dressed up. Since it’s not an actual work event, I have to agree with Shana. I think an open-toe shoe or a shoe with a little more interest IS a better choice if you want more “wow-power” (but only if you can actually dance in them!)

Accessories: This is where it gets fun. Again, since it’s a reunion and not a work event, Shana and I both think you should go bold and show off your personal style. Statement earrings and a handbag are an obvious easy way to add some more “oomph” and can easily be tweaked for different personal styles. Add a bold lip, a smokey eye, a glossy nude lip, or an edgy swipe of bold eyeliner, and you’re set!

The Options We Pulled Together

Eclectic: Surratt Beauty Smoky Eye Baton | Hispanitas T-Strap Heels |  Anthro Geometric Earring | Madewell Striped Pouch Clutch 

Chic:  Yves Saint Laurent Rouge Volupte Lipstick | Sam Edelman Strappy SandalChain Drop Earrings | Pearled Tibby Clutch

Edgy: Twinkle Pop Eyeshadow Stick | Cordani Platform Bootie | Free People Asymmetric Fall Earrings | Rebecca Minkoff Leo Envelope Clutch

Boho: Marc Jacobs Enamored Hi-Shine Laquer Lipgloss| Nine West Floral Heels | Anthro Crescent Hoop Earrings | Anthro Macrame Clutch

V’s Eileen Fisher dress has just a few sizes left (this is the most similar), but below are some others that would work in a similar way. For those of you who wear Eileen Fisher, you know they are usually cut generously, so I sometimes have to size down. I know they aren’t everyone’s personal style, but the idea with most of her designs are for the fabric to drape beautifully, so don’t panic if initially it feels like you’re wearing a sack, and don’t go too small with the sizing. Put on your heels, lipstick, and accessories and the “sack” will most likely look effortlessly chic and dramatic.

Shop More Eileen Fisher Black Dresses

Shop Accessories

V — once again, we hope you have a wonderful time next weekend, and keep us updated on how you decide to accessorize. I’m sure you will look great!

This is definitely a team effort, so what’s your go-to for adding some pizazz to a classic black dress for special events? Would love to hear more ideas.


9/19/18:  UPDATE FROM V 

V graciously gave us permission to share this beautiful photo of her at the reunion.  And we are the first to admit…Shana and I were TOTALLY wrong in the post.  The shoes look great!  Good going with your gut, V….  you wore the Eileen Fisher Stacked Heels (that are uber comfy) with your elegant dress and chic earrings, looked absolutely gorgeous, and could actually walk and dance all night long!  Thanks again for sharing the photo with all of us!



  1. This post is awesome! I love the options and the descriptions are so spot on. Crazy how you can change up the same dress. Would love to see more of these types of posts. They are so ‘real’.

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