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dresses Archives

I Love It, But Will I Wear It? A Matching Shirt and Skirt

I Love It, But Will I Wear It? A Matching Shirt and Skirt

May 20, 2026 Yes, this shirt sort of feels like a pajama top... but tucked into the skirt, maybe with a belt...

I followed the same images that I showed on Wednesday, so a few outfits will look similar, and you may recognize some accessories too!

This is NOT done because I'm inherently bone-deep lazy (although I could make a case for that!), but because I really want everybody to grow accustomed to wearing things frequently. But better, buy less, wear the heck out of it!

First up - a white cardigan. Always so useful in warm weather. And pink pearl jewelry... big deep sigh of smittenness...

Roll the sleeves just a bit, and pile on the gold! If one was inclined to try to make it through a season or two without buying ... View the Post

05.22.26 14 Comments

Tags: dresses, I Love IT But Will I Wear IT, pink, Start With Clothing, warm weather, white
A Two-Piece Dress in Pastel Floral - Some Ideas

A Two-Piece Dress in Pastel Floral – Some Ideas

May 20, 2026

So pretty! And a top that will cover bra straps, for those of us who founded our "lingerie under wraps" opinions decades ago:

I've been thinking of a system by which one could evaluate a two-piece set... Can it be worn with a light neutral? A dark neutral? Is there an accent color that will look good?

For example, this two-piece dress is just right with a light neutral (in this case white) cardigan:

The dress also looks good with an accent cardigan in orchid pink. (going to a wedding, anyone?)

The top is just the right touch with a simple linen set in light blue:

And this top can be really casual, with wild lilac shorts and a hoodie:

The skirt could be worn with a plain white tee shirt ... View the Post

05.20.26 22 Comments

Tags: dresses, warm weather, Will I Wear It?
Three Ideas for Two Dresses

Three Ideas for Two Dresses

March 18, 2026

I'm sitting here right now in a dress and a velvet jacket, with black "sneakerinas." For no good reason - I'm not going anywhere, and I'm not going to see anybody outside of my building. (which is not to say that my doormen aren't tremendously important to me!)

So I'm in a rebelliously "wear whatever you blinkin' well please" mood. And I think that almost every woman should have a fun dress..

How about something like this?

(I know, it's sleeveless. Your arms aren't perfect. YOU HAVE LIVED YOUR LIFE, AND YOUR ARMS REFLECT THIS. IT'S OKAY!)

I'm really on a rant...

 

 

First, it's easy to wear this dress with a classic cardigan and the normal accessories. This is the kind of outfit you ... View the Post

03.18.26 27 Comments

Tags: accessorizing, bag, dresses, scarves, shoes
Chic Sightings Green Dresses, and an Amazing Discovery!

Chic Sightings: Green Dresses, and an Amazing Discovery!

June 27, 2025

I wasn't sure at first - sometimes, a coincidence is JUST a coincidence. One shouldn't make too much of these things...

But then Belovedest noticed it too: LOTS of women are wearing green dresses! We were walking along the river last week, and saw FIVE women in green dresses... We didn't see five women in black, blue, red, yellow, AND white dresses.

Then today I went downstairs to our grocery store (in our building, the ultimate luxury!), and ran into one of my closest friends here in the building. Wear a green dress.

Okay, that's a sign! So let's look at some pretty dresses.

This first dress is pretty much exactly the color of peridots, so I gave this heroine some peridot jewelry. Realistically, her earrings ... View the Post

06.27.25 22 Comments

Tags: Chic sightings, dresses, green, warm weather
Five Ways to Wear a Two-Piece Dress

Five Ways to Wear a Two-Piece Dress

March 19, 2025

When I saw these matching shirts and skirts, I knew that I wanted to share them with you. What a practical, sensible, and just plain pretty option!

These two piece meet my "requirements" for a simple dress that can be worn a lot of different ways; if you don't wear dresses very often, it makes good sense to own a dress that offers you plenty of choices.

The easiest and most obvious way to wear this two-piece dress is with beige - summery and classic:

Okay, in the true hot weather, white is the most obvious neutral! Wear it - if it gets dirty, clean it. Don't be intimidated by the prospect of your clothing looking as if you actually WEAR it...

This scarf reminded me of one of our favorite accent ... View the Post

03.19.25 28 Comments

Tags: dresses, Five Ways to Wear
Love a Little Black Dress Start With a Scarf - The Bryan Yambao scarf by Echo

Love a Little Black Dress? Start With a Scarf – The Bryan Yambao scarf by Echo

August 9, 2024

One of our heroines fell instantly in love with a scarf, and had a business week travel vision...

She has a closet full of black dresses, but she's never dared to pack JUST black dresses for a business trip!

Why not? She's going to meet different groups each day she's away, and she doesn't care if she's known as the woman who wears lots of black...

Here's her color palette:

Her first dress is a mid-calf shirtdress... perfect with her suede belt, a red cardigan, and some other bits that pull everything together:

Her second dress is shorter, and has a small "moc" neckline. As much as she loves her golden yellow cardigan, she MUST have a brooch, so that she can conceal that annoying ... View the Post

08.09.24 20 Comments

Tags: black, dresses, Start With a Scarf, travel capsule wardrobe
Chic Sightings: Modest Dresses and Nude Accessories

Chic Sightings: Modest Dresses and Nude Accessories

May 29, 2924

Last week I went for another cortisone shot in my wrist, as well as the ten millionth re-fit of my arm brace - heavy lifting is catching up with my wee bird-like wrists!

But the thing I remember most from the entire adventure is a group of people I saw walking OUT of the office building as I was walking in...

Maybe 30 or 40 of them, equally split between men and women. The men were all wearing suits or blazers and trousers, and ALL of them were wearing ties. That, in and of itself, might have caused me to swoon.

BUT THE WOMEN!

All were wearing either:

(a) a skirted suit,

(b) a dress and jacket, or

(c) a dress - with sleeves, below the knee, no cleavage, with nude shoes!

Please, of course, understand ... View the Post

05.29.24 28 Comments

Tags: accessories, Chic sightings, dresses, warm weather
How to Wear a Blue Dress - 10 Ideas

How to Wear a Blue Dress – 10 Ideas

July 24, 2023

I heard from quite a few of you, asking if this dress could be worn with... well... navy, black, green and pink, so far!

So I decided to give this dress the attention it deserves, and see what the possibilities might be...

My gut instinct tells me that this dress will be great with any neutral, and with just about any other color that is of a similar intensity. Let's see!

Navy - of course! This would be a great dress to wear to a stuffy office environment, and then out for dinner:

I think this is a lovely combination - the green is soft, but equally saturated, so that it stands up to the blue:

If the weather is hot...

If autumn is approaching, and you feel like a darker color is the right ... View the Post

07.24.23 26 Comments

Tags: accessories, cardigans, dresses, jewelry

Year 2 – Japanese 24 Seasons of the Year – Taisho – Large Heat

July 21, 2023

Why yes, I DID miss the previous season - July 7, Small Heat. This year, Chicago is having a VERY cool summer, unlike so much of the world. It makes thinking about warm-weather clothing sort of difficult! 

But let's pick up with the current season...

At this point in the year, when major retailers are pushing cool-weather clothing at us, we can at least find nice dresses...

If I were to only own 1 dress, this might be a candidate. The dark background would make it easy to wear dark tights and flats, with a navy sweater, in cool weather:

Similarly, this dress is made to be worn with a cardigan or blazer:

I'm currently wearing the black version of this dress, with amethyst jewelry to match ... View the Post

07.21.23 17 Comments

Tags: dresses, Japanese 24 Seasons, warm weather
A Travel Capsule Wardrobe for a Dressy Weekend Start with Art - La Trappistine by Alphonse Mucha

A Travel Capsule Wardrobe for a Dressy Weekend: Start with Art – La Trappistine by Alphonse Mucha

June 23, 2023

Now that summer is finally here, it seems that many of us are being called upon to get gussied up!

Yes, the term "gussied" always makes me laugh...

It's always more challenging to find warm weather clothes in warmer shades...

It might be a wedding weekend, but it might also be a graduation, or an anniversary celebration - there are plenty of reasons to get dressed up and party in the summertime!

Our heroine isn't at all sure what she wants to wear when, so she's bringing an assortment of dresses with her, as well as a couple of tops and pair of bright jeans. Once she arrives, she can check with the organizers of things to see what will be most appropriate when.

And then she will wear what makes ... View the Post

06.23.23 30 Comments

Tags: dresses, Start with Art, travel capsule wardrobe, warm weather
Japanese 24 Seasons of the Year – Shunbun – Vernal Equinox

Japanese 24 Seasons of the Year – Shunbun – Vernal Equinox

March 20, 2023

I'm writing this on Saturday morning; the temperature is WAY below freezing... sigh...

The first day of spring is my anniversary! 19 years - it seems like almost 2 decades...

I was thinking of pretty outfits for Easter, or some other wonderful Spring dressy occasion. Having one truly lovely outfit in your closet is only right!

 

A dress with smocking looks MUCH better on a person, rather than just stark in a photograph...

 

First sign of Spring in a lot of the world:

 

A pretty blouse or shirt can be worn a lot in the warm weather - with a skirt, certainly, but maybe shorts?

 

At a distance, this skirt doesn't seem to have much pink in it - you need to ... View the Post

03.20.23 22 Comments

Tags: dresses, Japanese 24 Seasons, skirts, Spring, warm weather
JAPANESE 24 SEASONS OF THE YEAR – TAISHO – LARGE HEAT

Japanese 24 Seasons of the Year – Taisho – Large Heat

July 22, 2022

Well, this is timely! I was just out on Michigan Avenue, the temperature is around 90 degree Fahrenheit, and the most comfortable women I saw were wearing loose dresses...

And so was I!

The most important thing to remember on days like this is to stay hydrated! And of course, protection from the sun is critical...

It's possible to wear black, if you've got your route planned so that you can stay on the shady side of the street! If you're not sure about how sunny it may be where you're going, you may want to choose something in a lighter color.

This is how it feels...

Even if you're somewhere surrounded by buildings and pavement, you can wear pretty flowers!

You might find that ... View the Post

07.22.22 17 Comments

Tags: accessories, dresses, Japanese 24 Seasons
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The Vivienne Files is a unique personal style blog with carefully-selected capsule wardrobes based on color palettes drawn from works of art, nature, and more. It helps women buy less clothing, and to love what they buy. Read more...
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