what makes a good vintage dress

you have to kiss a lot of frogs to find your prince, or whatever they say!

The world of vintage is infinite beyond comprehension. Because it’s basically the entirety of human existence on Earth…told through clothing.

And it’s kind of like a black hole in that it’s a one-way door: once you get sucked in, you can’t go back. The physics don’t work. Think about how many vintage/secondhand store names tap into this existential feeling of vastness: Wasteland, Afterlife—even the Swedish founder of Buffalo Exchange chose “Buffalo” because it reminded her of the *American West* and its associated expansiveness.

I spend most of my time learning about vintage online, through a combination of social media, Reddit, Wikipedia, Vogue Runway app, the synopsis section of papers on JSTOR, and online vintage/archive stores. It’s how I’ve slowly developed a decent recall for what pieces from what designers are from what year…and the ability to ID them in the wild, which is the most rewarding part! I admire the experts among us who can rattle off vintage knowledge with the reflexes of an F1 driver. (Petition for wine bars to host fashion history trivia nights?)

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But visiting a brick-and-mortar store is really what rekindles my interest in vintage.

A dozen slumbers or so ago, I popped into Pretty Penny Clothing in Oakland. The curation is not based on designer brands, but rather on artistry and historical relevance. And it’s serious vintage! You won’t find a random Forever21 dress from 2014.

I wasn’t really looking for a specific item, but the dress rack drew me in with its colors and patterns. It seems everyone on Substack is looking for a wedding guest dress though, so maybe I subconsciously had dresses on the brain even despite not having any weddings on the social calendar this year! I

Can we also agree that shopping out of urgency sucks?? I swear, House of CB and Reformation must make a hefty % of annual sales because we don’t know what to wear to a wedding. I prefer to shop out of curiosity and exploration, taking my time to add special pieces to my wardrobe so that when I have a matrimonial ceremony to attend…I already have outfit options I’m excited to wear.

These are the five dresses I tried on, what learnings/inspo I took from them, and how that guided me to purchase a dress off Vestiaire that I can’t wait to wear all summer.

dress #1

This was the first item I pulled off the rack because I could tell it was 100% cotton. Proof that a cotton dress CAN look/feel fancy! It’s a bit of Bridgerton-esque style without the intense empire waistlines. I was picturing this with a pair of long silk opera gloves. Also, maybe you can tell from the picture? But it was doubled lined. The top layer is sheer white but the inside is a light minty blue. This created a really pretty effect and assuaged any worries about a white dress being see-through.

Learnings:

• You don’t need a shiny satin weave to convey fanciness.

• Double-lined garments are an easy way to quickly ID quality.

• I like how a floor length dress looks on me!

dress #2

Okay this one I actually looked at initially on the rack and flipped past it because it looked very “skater style” cut which I don’t like.

But 5 min later I looked at the print again and decided to try it on anyways. It reminded me of Betty Draper’s dinner party dress (apparently called the “Sad Clown Dress” from Johnny Herbert).

Learnings:

• The pattern was so captivating…it’s a dainty floral but not like those photorealistic floral prints. It’s more Marimekko…round, blobby, graphic. I’m a fan.

• I love prints that mix many blue-ish shades: periwinkle, robin’s egg, earl grey.

• I typically do not like fit and flare cut dresses. But I like this. And I think it’s due to the 1950s-specific design like the bust shaping and drape of the skirt. It didn’t look like a skater dress when I put it on.

dress #3

I have been watching so much TV set in the 60s, this one was screaming to be tried on. I’ve wanted to experiment more with raised collars/mandarin collars and thought the zigzag neckline of this was interesting. When I tried this on, I thought of the scene in Priscilla where Elvis is being a controlling prick and tells Cilla that she shouldn’t wear prints because they overwhelm her stature. I personally like how “busy” this print feels, but wish the hemline were shorter.

Learnings:

• 60s style shift dresses are cute, but I’m on the short side and need a super-mini hemline. This length made me feel conservative.

• Reminder that there are sooooooo many variations on floral prints. The ditsy rose print is popular with contemporary brands but pretty much every interpretation of a floral print has been done at some point in vintage clothing.

dress #4

The green ribbon and lacy neckline of this jumpsuit drew me in like a moth to a flame. Maybe I should wear more purple??? This try-on was purely experimental I knew it. I just wanted to see how it would feel. Unfortunately, it felt like clown pajamas on me and not in a good way.

Learnings

• I hate this cut of jumpsuit. I feel like it renders me one dimension short. Flattens my presence. Maybe it needed to be sleeveless? Or maybe it needed to be blouse top. Yeah, I could see this being more cute with some high waisted flare jeans.

• Green ribbons are cute though. An unexpected detour from the pink and blue ribbons on corset cover tops I’ve been bookmarking on Etsy.

dress #5

I almost bought this one! Seriously, if it had not been nylon, I would have taken it home. The tag said it was made in the 70s in Hong Kong. I pictured Maggie Cheung from In The Mood For Love wearing this in a hypothetical sequel.

Learnings:

• This is the right length of minidress for me

• I love these muddy pink colors

• I like the 70s style zip front with the ring zipper detail

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Then I went home. Digested the learnings and started casually browsing vintage dresses online, guided by my observations from the try-on session.

I think I started with “1960s mini shift dress” and went from there. Saw some Pucci. Liked those prints. Hopped around different decades. Gravitated towards Palm Beach-y color palettes. Ended up in the 90s/y2k category. Saw this dress and LOVED it.

vintage D & G linen-cotton dress

This is the mini length I wanted, a fully cotton + linen fabrication (YAY!) and the shaping of the bust makes this piece feel vintage. I got it for $140 on Vestiaire Collective. I plan to wear this with my Miu Miu purses and heeled Suzanne rae fur slides.

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And here are dresses I bookmarked along my search, but did not buy. They served as excellent visual inspiration though. Maybe it will be the perfect dress for someone else.

1970s polka dot dress (size 12)

i just know the drape of this will hang beautifully.

1960s peach party dress (size 2)

the peach, the bows.

1960s cabana sundress (size 6)

the hat styling is genius. turns the dress into something more funky, more world-traveling eccentric glamorous child-free auntie. i love that slit design detail in the middle. begging to be worn with split toe tabis.

1970s Vested Gentress shift dress (size 16)

pretty stand collar design and green piping along neckline and armpits.

xoxo

viv