In Which The Directrice Puzzles Over Shoes

I’ve been craving a shirtdress recently. I haven’t owned one in years, but they’re back in and I want part of the action.

I found this denim dress at Brooks Brothers. ON SALE.
Cute, right?
But what shoes to wear with it? They (the magazines, the blogs) are showing shirtdresses with loafers and mules styled like loafers, but that seems a little heavy to me.
Not sure about footwear
I’m not sure about footwear

You can't just wear the flip-flops you wear around the house
I don’t think I can just wear the flip-flops I wear around the house even though they don’t look half-bad
My go-to ballet flats look a little too schoolgirl with this dress.
Low heels would just be weird.

I need something that has substance, but not overwhelming weight.
I need . . . I need . . .
I need the Dainty Sirano
I need the Dainty Sianos

They work, for reasons that I can’t fully explain.
Boom! Ask, and ye shall receive
Ask, and ye shall receive

If I may so say, this was an unusually good idea
If I may so say, this was an unusually good idea
You may have noticed that this dress is a little shorter than is my preference?
It’s above the knee — but the clever shirttail hem provides some visual compensation (more like distraction) and keeps it from looking inappropriate. I think.

The dress did not come with a belt.
Actually, it was kind of a shapeless thing.
In this picture, it looks kind of awful
Not shown to advantage

But I loved the tiny pockets and orange top-stitching — so I tried it on and used the black belt I was wearing that afternoon to cinch the waist.
I knew that I would be able to find a better belt at home.
Brimming with good ideas
Brimming with good ideas

Metallic belt in copper
I bought the belt on faith and its purpose was revealed later
Which I then did do!
I’ve had this belt for years. It was one that I purchased without a clear purpose, simply because I loved the copper color, metallic finish and vachetta trim.
First runner-up was the tortoise belt I wore with a black dress last week.

Two last photos to show the bag, which has just a little orange in it, too.
Note the orange in the bag
Note the line of orange running through each flower

If you are looking for brogues, the search is over:

Dress: Brooks Brothers Denim Pullover Dress; Belt: JCrew; Shoes: Dr. Martens Siano Oxford; Bag: Orla Kiely

18 thoughts on “In Which The Directrice Puzzles Over Shoes”

  1. That dress certainly looks better than the way BB styled it! The belt is perfect. Speaking of Brooks Brothers, what do you think of the Zac Posen influence? I pretty much hate it, I hope they tame it for next season.

    • Oh no, Julia! I want us to agree on everything, but I am afraid we may diverge here. I think I like the ZP influence — which is funny, because I don’t like his regular line. I find it too exaggeratedly feminine. But I thought there were many charming things in Brooks Brothers this spring, like my denim dress and the dresses I showed last week. I’m not sure if he designed all of it, or just some of it. I ordered the green dress and it is made of the most gorgeous Loro Piana lightweight wool. I hope the next season is more to your taste!

  2. My commute includes a was healthful walk and I’m always looking for nicer than athletic shoes for my walk. Are they comfortable from the first wear?

    • Hi Ginger — The Doc Martens are stiff and heavy, so I wouldn’t recommend them for significant walking unless you are into that (which I kind of am). The Cole Haan shoes are very comfy from the get-go: supportive and cushioned.

  3. Directrice you styled that so much better than BB. Makes me almost want to take a second look.

    Julia the Zac Posen collection is not very attractive. I also noticed a lot of “performance fabric”. I thought one of BB claim’s to fame was their use of natural fibers?

    Ginger R. if you are asking about the Cole Haan Zerogrands the answer is yes! They also come in so many wonderful colors and finishes. I am looking to add their ballet flat (unlike any ballet flat I’ve come across) to my closet.

  4. Hi, Directrice, I can see that some of the dresses would fit in with your aesthetic, and I have seen them in person and the fabrics and tailoring are beautiful. But the whole line is such a departure from what I loved about Brooks Brothers, beautifully made classic separates. And what they are offering is priced higher. I hope they reach a middle ground next season. Last fall, I bought three jackets, several pairs of pants, some sweaters and shirts, and a few scarves but this spring I bought nothing. But that dress looks great, and I can’t wait to see the green on you. ( I did love that red shirt dress they had in the first spring offering.)

  5. Fabulously stylish, as always: it’s all in the details. And if the dress was any longer it would drown you, even with a belt.

  6. I love this, and a great way to wear denim on a day I’m not wearing a denim jacket.

    Directrice, what might you wear over this if you worked in an over-airconditioned office where you need at least two layers of clothes on even the hottest summer days? It’s so perfect I’d hate to add anything, but I sadly have to have layers for work.

    • Lynne — I puzzled over your question and here are my thoughts. A jacket or sweater with this dress would be tough because the dress is cinched at the waist but blousey above and below. Regardless of how short or fitted the jacket or sweater might be, it will be bulky. So . . . If the weather outside were cool, and you needed a layer for warmth, but knew you would require that warmth all day (inside and out), I would wear a slim-fitting long-sleeved tee shirt under the dress. If the weather outside were warm and you just needed to bundle up inside, I would try one of two things. First, you could wear a large scarf wrapped around your neck several times; you might be surprised how much this can help. See The Virtues of Large Scarves. Second, you might want to buy a very lightweight wool or linen wrap. A wrap would be so much more chic with this dress than a jacket or sweater.

  7. “Dainty.” Uh huh. Anyway, I see that you swapped the laces for dark ones and made the floppy bows prominent. Nice — gives a good contrast with those dainty lugs. (Is that what they call them? As in lugheads?)

    • Lug soles! It was Doc Martens who called them “dainty” — I am just following their lead. A young woman in my office building stopped me the other day and said, “I love those shoes, they’re really gr — ARE THOSE DOCS??” She was amazed, I was thrilled.

  8. Like the whole combination and the belt makes the dress colors more pronounced. The shoes worked carrying the theme. You have to be pleased with this outfit. Great to have for summer through fall. Kate

  9. The dress looks fantastic on you — but for me, pockets over the girls are a no-no. It’s difficult to find much of anything in denim that doesn’t have those pockets, including almost all jackets, shirts, and dresses. Crying face emoji! But you look wonderful.

  10. I love what you did with both belt and shoes here to elevate this dress – so cute, and the blue-orange combo just sings. I hit a similar shoe dilemma with a new shirtdress just this morning myself ( — another “looks like nothing on a hanger” number, but with my comically hourglass frame it found some structure on which to land). My dilemma had the added difficulty of a day starting in the mid 50s but expected to get into the high 80s. I resolved it with knee high cognac boots for days, with a pair of silver thong sandals in my car when I leave work — we’ll see how it goes!

  11. Directrice – Thank you for your thoughtful ideas on how to wear this in a cold office. I’ll go with a scarf or wrap, which I can easily add to sit in a freezing office or meeting, and remove when I’m not at work.


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