Anonymous
Post 06/10/2026 13:12     Subject: Re:How do I wear a button down shirt dress and look nice?
The downside is they always look like pajamas.

The upside is they feel like pajamas and are somehow socially acceptable, even in the workplace.
Anonymous
Post 06/10/2026 12:16     Subject: How do I wear a button down shirt dress and look nice?
1. be tall

2. do not have large breasts

3. have it hemmed a bit to show a little waist, the straight up and down look isn't flattering
Anonymous
Post 06/10/2026 12:10     Subject: How do I wear a button down shirt dress and look nice?
Anonymous wrote:I don’t care for shirttail hems. They look sloppy to me.


This is my issue. Shirttail hems were designed to be tucked in. Like that is why they are shaped like that. If you wear an actual shirt with a shirttail hem not tucked in, okay, it's a more casual choice, like rolled hems on jeans or chinos. But a dress with a shirttail hem looks dumb to me. It's a dress. It should have a dress hem.
Anonymous
Post 06/10/2026 11:50     Subject: How do I wear a button down shirt dress and look nice?
I’m tall and thin and they look terrible on me. I think you also have to have strong facial bone structure to counterbalance the shapelessness of the dress.
Anonymous
Post 06/09/2026 18:19     Subject: How do I wear a button down shirt dress and look nice?
I really like this look. I’m petite and anything belted looks great on me.
Anonymous
Post 06/09/2026 18:05     Subject: How do I wear a button down shirt dress and look nice?
You could go with a more refined silhouette. This has more feminine detailing while still being relaxed. It gives you more options for accessories if you want to dress it up.

https://www.cos.com/en-us/women/womenswear/dresses/minidresses/product/sleeveless-cotton-poplin-shirt-dress-white-1339729001

Anonymous
Post 06/09/2026 17:46     Subject: Re:How do I wear a button down shirt dress and look nice?
Anonymous wrote:
Anonymous wrote:At that length, it's meant to be super casual and works best with sandals or cute sneakers, a sun hat, and a straw or canvas tote. It's not going to work in every setting and isn't meant to be polished or dressed up. I have the Frank & Eileen version that I wear pretty often when we're at our summer house . . . the appeal lies in the ease of throwing it on to run to the store, grab coffee in town, or as the equivalent of a housecoat when we have guests.

As the PP above notes, the longer version works better if you want to style it to look more put together:



I might be wrong, but this looks like linen to me. I honestly think the less crisp version is part of what helps make it look better.


Agreed. It needs to be a breezy, unfussy fabric, midi length, and belted to avoid the whole “had a one night stand and grabbed his work shirt to wear at breakfast” vibe that those women in the crisp white minidresses are giving.
Anonymous
Post 06/09/2026 13:36     Subject: How do I wear a button down shirt dress and look nice?
Anonymous wrote:A longer hemline and a belted waist. Both of these women look like they forgot their pants.


Exactly what I was thinking 😂
Anonymous
Post 06/09/2026 13:34     Subject: Re:How do I wear a button down shirt dress and look nice?
Anonymous wrote:At that length, it's meant to be super casual and works best with sandals or cute sneakers, a sun hat, and a straw or canvas tote. It's not going to work in every setting and isn't meant to be polished or dressed up. I have the Frank & Eileen version that I wear pretty often when we're at our summer house . . . the appeal lies in the ease of throwing it on to run to the store, grab coffee in town, or as the equivalent of a housecoat when we have guests.

As the PP above notes, the longer version works better if you want to style it to look more put together:



I might be wrong, but this looks like linen to me. I honestly think the less crisp version is part of what helps make it look better.
Anonymous
Post 06/09/2026 13:24     Subject: How do I wear a button down shirt dress and look nice?
These all look like something you wear on vacation over your swimsuit to get lunch or walk around the resort. Especially in white.
Anonymous
Post 06/09/2026 12:16     Subject: How do I wear a button down shirt dress and look nice?
Being thin is half the battle. Otherwise be tall.
Anonymous
Post 06/09/2026 09:57     Subject: Re:How do I wear a button down shirt dress and look nice?
Anonymous wrote:
Anonymous wrote:At that length, it's meant to be super casual and works best with sandals or cute sneakers, a sun hat, and a straw or canvas tote. It's not going to work in every setting and isn't meant to be polished or dressed up. I have the Frank & Eileen version that I wear pretty often when we're at our summer house . . . the appeal lies in the ease of throwing it on to run to the store, grab coffee in town, or as the equivalent of a housecoat when we have guests.

As the PP above notes, the longer version works better if you want to style it to look more put together:



This looks super unflattering to me even on the model. Like a saggy top and very round in the belly which I am sure she's not.

These dresses need a bit of taper in the middle which most don't have (otherwise there is a ton of extra material when belted) and yes it takes a very toned thin tall body with nice accessories.


OP is specifically asking about this type of shirtdress. They are what they are, and they are not supposed to be body conscious. The longer versions are easier to style because you can belt them, but they are intended for comfort and ease.
Anonymous
Post 06/09/2026 09:50     Subject: How do I wear a button down shirt dress and look nice?
I don’t care for shirttail hems. They look sloppy to me.
Anonymous
Post 06/09/2026 09:42     Subject: Re:How do I wear a button down shirt dress and look nice?
Anonymous wrote:
Anonymous wrote:At that length, it's meant to be super casual and works best with sandals or cute sneakers, a sun hat, and a straw or canvas tote. It's not going to work in every setting and isn't meant to be polished or dressed up. I have the Frank & Eileen version that I wear pretty often when we're at our summer house . . . the appeal lies in the ease of throwing it on to run to the store, grab coffee in town, or as the equivalent of a housecoat when we have guests.

As the PP above notes, the longer version works better if you want to style it to look more put together:



This looks super unflattering to me even on the model. Like a saggy top and very round in the belly which I am sure she's not.

These dresses need a bit of taper in the middle which most don't have (otherwise there is a ton of extra material when belted) and yes it takes a very toned thin tall body with nice accessories.


“ saggy top and very round in the belly”

I’m so glad when people post this because it puts the implicit insanity here on display. She’s just standing funny.