Styling a Summer Dress Three Ways (Causal Daytime, Date Night and Office)


Reader Daina wrote in with a hysterical two-part question (more on part two later).  She asked:

"I would love to put together one great day/lunch outfit that I can then leverage for work or even a casual date night with my husband.  I am at a loss for what to choose since: (1) I have to shop online; with a baby and toddler there is no way I am going to get to a mall; (2) I can’t figure out what will look appropriate for both work/lunch/date night; and (3) whatever I choose has to be able to travel (e.g., no linen!) since I’ll take the train to NYC and, if I use the outfit for work, that usually involves travel too."

When looking for maximum flexibility, it's really hard to beat a dress.  As long as you stick to something simple but well constructed in a non-fussy fabric, a dress can easily be worn while running errands, out to lunch, at the office, or sexed up for date night.  The key to keeping the look effortless (and appropriate) is in the accessories. 

Here is one of my very favorite summer dresses, styled three different ways for three different situations. (The dress is J.Crew's Blakly dress.  It is unbelievably flattering – this dress does all kinds of good things to "the girls" while somehow disguising a poochy stomach.)

Day Dress

This dress can be fancy, but when thrown on with a cross-body bag and flat woven sandals it has that "this old thing?" vibe.  A simple wood cuff and sunglasses are my go-to summer accessories.




Date Night

The tried-and-true formula for date night is to swap your flat sandals for sexy heels, and your diaper bag for a small clutch.  I changed things up a bit and used wedges ('cause I like to be comfortable in the summer) and picked one of those bright, over-sized clutches that every fashion blogger seems to be carrying these days. (Here's a DIY if you're interested).  And the earrings are just pretty.  They'd look so cool with the neckline of the dress.   This would actually work great for a wedding also…

SummerDress- Date Night





I put two work outfits together – one for now, and one for the Fall.  Wearing a summer dress come Fall is one of my very favorite tricks when trying to rationalize a price-per-wear decision.  Besides, this teal color was made to pair with navy.  And cognac. 

In any case, the ruffle of this dress would look so cute peeking out from under a blazer.  Belted or not.  Either way works.

Summer Dress - Office - Now and in the Fall




But this dress.  Seriously flattering – in every man's favorite way (if you know what I'm sayin, wink wink).  There's no. possible. way. anyone will be looking you in the face.  Which, if your kids sleep like mine and M's…that might be a good thing.  No one will notice the dark circles or puffy bags…they'll just be hypnotized by your…huge tracks of land surrounded by a little ruffle. (And look for it in J.Crew's Factory store…I often see a version there…)



ps.  Daina – more for you later….


  1. Thank you! Thank you! Thank you! You have made my day and my summer. I love the suggestions and I’m shopping right now, between feeding kids, working and sweatin’ in the steamy NE.

Leave a Reply