The Original Twenty Year Old Dress

Last week, I showed you a new dress and predicted that I would be able to wear it for the next twenty years. Some of you may have thought I was speaking hyperbolically for effect.

Non, non.
I was as serious as climate change.
And I was speaking from experience.
Here is the original Twenty Year Old Dress.
Yeah, my dress is old
Yeah, my dress is old

Where is that woman headed? Funeral? Bris? Award luncheon?
I bought this dress in 1997, when I was a summer associate at the firm where I am now a partner.
Ah, the more things change, the more they stay the same . . .
I will go out on a limb here and advise: Every Woman Needs A Timeless Dress Like This.
Why? you ask.
Because this is the dress you wear for the following occasions: work, when you just can’t think of anything, but need to look polished and professional; funeral; wedding (different accessories!); concert or fundraiser where the dress code is not clear.

What is “a timeless dress like this”? It’s a short-sleeved or sleeveless shirtdress with an a-line or column-style skirt that ends mid-calf with a straight hem — no novelty hems on the timeless dress. Ideally, this dress will be made of a heavy linen or fine cotton poplin or twill.
A little detail, like this yoke with top-stitching, is a plus

I bought this dress at Banana Republic, and hats off to BR for making a dress of such outstanding quality. The dress’s longevity is due, in part, to weight fluctuations (lighter years, heavier years) which have allowed this dress to rest and collect itself during certain summers (2004, 2005, 2006, 2010, 2011).
I also realized c. 2008 that the armscyes were gaping a little and asked my tailor to add a dart along the side to correct the fit. Sometimes you have to live with something awhile (1o yEaRS?) before you realize something isn’t quite right.
Sometimes I astonish m'self
Sometimes I astonish m’self

This is the dress
This dress came with a fabric self-belt — but I usually wear a glossy black calf leather (funeral!) or animal print belt (bris!) with it, to change the look in subtle ways.

And now a quick look at accessories!
A bracelet and watch for work . . .

Perfect for a work day and a concert after work. Indeed, that was just its trajectory last week!
Here are some timeless dresses for your consideration.

Max Mara Studio Cadine Dress
Max Mara Studio Cadine Dress
Altuzurra Kyoto Button-through Midi Dress
Altuzurra Kyoto Button-through Midi Dress; do up all the buttons and this is a modern classic
Saloni Natalie Criss-Cross print Shirtdress
Saloni Natalie Criss-Cross print Shirtdress; I would consult with the tailor about narrowing the sleeves
Toga Tafetta Tassel Trimmed Dress; this one checks some of the boxes
OK, not timeless . . . but fun; Toga Tafetta Tassel Trimmed Dress

Have a fantastic weekend!
Dress: Banana Republic (only available to Dr. Who); Shoes: Tory Burch: Bag: Coach Borough Bag; Bracelet: John Hardy; Watch: Michele Urban

12 thoughts on “The Original Twenty Year Old Dress”

  1. If only I had bought the Button-Through dress 20 years ago I could have made full use of the unbuttoning feature in my youth. These are all quite lovely, though I might like yours best. What kind of layering do you do with it?

    • You’ve stumped me, Regina. This is one dress that I don’t layer, in part because I like it’s long, simple lines as they are. If I were to wear anything over it for warmth, it would be a little jacket or cardigan — but a pretty wrap (maybe in a yellow-orange color?) might be better.

  2. Simply divine – however I need sleeves. Maybe I’d layer it like Regina suggests and use a floral or striped T or blouse. I love the length, I love the versatility.

  3. For all my edginess at times (like when SF convention folks think I’m cosplaying Black Widow, but I’m just in my normal clothes), there is nothing like a classic dress to get you through the ambiguous times. I love yours here and the recent one you bought. Yesterday at my daughter’s graduation, I wore an OLD favorite von Furstenberg wrap dress. Emphasis on old. It’s also a classic that can take you anywhere and lets you fluctuate in weight and shape. I love that wrap so much, a have a few in different colors. God bless the classic dress!

  4. Those dresses are so chic, will be timeless, and have the longevity experience already built in. They all share your own dress features. Loved the shoes that were shown with them all. Kate

    • I know, Kate — the shoes are great. One of the reasons I love is that they do such a good job creating outfits and accessorizing them. Really talented buyers, editors, and stylists.

  5. Shows what consistent style and good taste you have throughout your life, which is surely a comforting thought! Interesting to compare the quality with a newer dress from the same brand. I used to buy a lot of vintage clothes and was amazed at the different sewing techniques from age to age, especially with fastenings. Some of the dresses had such complicated and numerous fastenings. I really love the simple midi skirts from the 70s and 80s which close with one or two buttons at the waistband on the left, and a very generous overlap of fabric and maybe gathers in front of usually just one pocket on the same side as the buttons. Whenever I don’t know what to wear I wear a DVF wrap dress or a black dress quite like yours.

    • I have nothing if not my good taste, Justine! It is remarkable how high the quality of clothes made by mid-level retailers was 30 and 40 years ago — and how sad that that quality of clothing is becoming an exception in the marketplace. (I do marvel at how well JCrew clothing is made.) If you haven’t read Overdressed by Elizabeth Cline, I think you’d find it fascinating (though depressing).


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