Reader Quandry: I’m in My 30s! I Need a New Look! I Like 1960s New York!

Reader style icon: Isabella Blow.

Hello, readers! Last week I received another email from a reader looking for advice about how to spruce up their wardrobe and find a new look. This was an amazing email filled with back story, details, style references, and pictures! Literary emails are my favorite kind of emails. Here’s what you need to know: this particular reader is in her early 30s, put on weight for two years, and has lost almost all of it again, which means that her wardrobe is decimated.

Her “old go-to store, Anthropologie, has gone all middle-aged and frowsy, so [she doesn’t] even know where to shop. And so [she] ends up shopping at cheap places like H & M and Forever 21 and things end up falling apart and looking crappy.” Indeed they do!

Here’s the part that really clenched it, though:

Most troubling: I don’t have a style anymore. Like, an overarching thing I’m going for.   When I was younger, I used to go for a look that I thought of as “dissipated librarian,” or maybe “louche grad student.” And when I was younger still, I was a pink-haired emo  chick. But that no longer appeals. As my dad is fond of saying, I’m built like a brick shithouse (thanks, Dad, and ew): big boobs and a big butt and a small waist. Oh, and I am very long-waisted and have long arms. My best colors are blacks, browns, pinks, reds, and navy.

This could be your next outfit!

Though I haven’t had any physical fluctuations between my 20s and my 30s, I can completely identify with this reader’s predicament and I’ve spoken to a lot of people–of every gender–who have had a similar rough transition between the decades. There you are, going about your business throughout your 20s and then BLAMMO! Suddenly all the experimentation doesn’t quite feel right anymore. You don’t want to suddenly start dressing like a schoolmarm, but the dramatic individuation phase of life is pretty well concluded, as are its fashion expressions. To complicate matters, many women find that their metabolism slows around the same time, giving them a whole new body to work with ON TOP of shifting identity issues.

So. This reader and her conundrum.

Wearing a lobster around her neck because she's Isabella fucking Blow.

The rules, set by her:

No tall heels, no intense cleavage, no bold prints, no ponchos. But she’s interested in pencil skirts, capes, shirt-dresses and loafers, skinny jeans, Isabella Blow, Anna Karina, Alexa Chung,  Iris Apfel, and her friend’s three-year-old.

Favorite look:

1960s Intellectual Manhattan, which means “amazing glasses and really kick-ass structured clothes.”

Anna Karina. Wearing amazing glasses.

Kick-ass structured clothes.

This reader already knows what she’s drawn to, so that’s a great first start. Based on what she’s written, it’s clear to me that she identifies as some sort of creative intellectual. Great!

And she knows her body type: hourglass. Great! You know who else was an hourglass girl with a big butt and big boobs and a tiny waist in the 1960s? Marilyn Monroe. I know what you’re thinking: “WHAT?? That’s the OPPOSITE of the NY Intellectual look!” Actually, Marilyn had some pretty sweet-ass simple looks going in the ’60s. Let’s look:

Easily the greatest picture of her ever taken. Notice the neckline.

Again, notice the neckline.

And if you ever needed a reason to love LA, here it is. This also might be Italy. Unclear.

Marilyn brings me to my first point for the well-endowed woman who doesn’t want to flash cleave (though if you have, use it, says this tiny-boobed woman)— necklines. While you might not want to go full-on into a scoop neck if you’re worried about cleavage, the well-endowed look great in wide and open necklines. Low, wide necklines break up the chest area visually. My friend Maria (with whom I checked to see if I could post pictures) really makes good use of necklines. Here she is in a V neck dress with a plum-colored cardigan on top, which creates a nice angular look. In fact, if navy looks good on you, look into rich shades of plum. It’s a nice way to subtly add some color without being like LOOK AT ME! COLOR! WOW!

Maria with an excellent use of a V.

She also always wears RED lipstick, which looks incredible on her and which I recommend for anyone with dark hair and a Mediterranean skin tone.

Black V neck, color on top, red lipstick. Quite the picture of a sophisticated woman riding a bicycle built for 4. No really, that's what's happening.

Here’s Joan (Christina Hendricks) also doing the neckline right:

Joanie is so cute. Big boobs, big butt, little waist!

Even though you don’t like bold patterns, you might want to experiment with black and white patterns under a solid-ish layer. Stripes, large polkadots, etc. can actually work really well, especially if you’re paring it with dark jeans and a ’60s style jacket/coat. They’re an easy way to make an outfit really pop with little to no effort.

I love this woman.

Another great way to spruce up an easy outfit is to go monochromatic and then get an excellent accessory, like a big necklace.

This bitch knows something the rest of us don't. Anyway, that necklace is AMAZING! If you were wearing all black or navy with a V neck... imagine!

The ’60s had some incredible jewelry. It was all enamel all the time.

Enamel wild flower necklace. I would wear the crap out of this.

This brings me to an important point. The 30s are all about the use of smart subtlety. It’s a great time to integrate the highlights of your 20s wardrobe experimentation into a sophisticated adult style. Keep a little spirit of whimsy and “I could give a fuck,” but blend it with “I have a good job and I think about things and I likely won’t drunk punch you.” What you’ll get is a new you that still winks at the you that got you there. If you put something on and it feels too “adult” or “soccer mom,” then draw on the 20s you to find an accessory, pair of shoes, etc. to add that cuts that feel and freshens it up.

Every time you get dressed, imagine you’re about to head off to some mid-century intellectual bohemian dinner party on the upper whatever side where you’ll smoke and drink cocktails and talk about what a dick Hemmingway was despite his genius.

And build your new wardrobe from what you know you love.  Most importantly, remember that it’s ok to fail a little. Your 20s self knew that. I think we hit our 30s and expect to have some grand idea of who we are and how we should look. Fuck that. Keep having fun with your look!

Where to start/buy:

1. A Black V neck shirt (not a straight up t-shirt)

2. One shirt with a “fun” neckline… I’ll leave this to you. It could be a geometrical silhouette, a blouse with a flouncy neckline (example: the 1st image of Joan), etc.

3. One shirt with a black and white pattern and a low neckline

4. One chunky necklace of your choice

5. One brightly-colored necklace of your choice

6. One basic pant (dark, skinny jeans all the way to JUST below the ankle)

7. One pair of leather “mod” ankle boots with a pointy toe, not a square or rounded toe

8. An additional pencil skirt bought in conjunction with one of the shirts and with one of the necklaces in mind

9. A jacket with an interesting cut (could be structured) in a color that you can settle on (A COLOR, not a neutral). Use navy as a jumping off place… think plum and other rich/warm shades.

10. One ’60s chunky bracelet.

So. Resources. 

If you need jeans, PZI makes great skinny jeans for women with a small waist and big butt. They’re also reasonably priced.

Redbook has this article about jeans for all manner of butts.

Need Supply has great accessories. And they often have good blouses.

Honestly, I often check Etsy for vintage ’60s attire. I don’t really like much of the DIY stuff, but their vintage selection tends to be good quality and good prices. Especially for ’60s jackets and dresses.

The best thing I did last year was “join” It’s free to join and you custom results to your tastes and they have EVERYTHING. I’ve found stores and products I never would have known about otherwise.

Beacon’s Closet in NY is an amazing used clothing store with online shopping.

Oak is expensive, but their sale accessories are not.

Bizarrely, Macy’s is a great place to find super sale shoes. Shopping online with them is a miserable experience and they for some reason love to light their shoes in vomit-inducing ways, so just go in.

And you’re going to laugh at me, but my friend Alex gave me a tip that Lord and Taylor is actually a good place to get high quality, good looking sale items if you’re willing to wade through all the old lady stuff.

For cheap stuff that won’t fall apart, you should just go to the giant Goodwill in South Boston. All cheap chain store stuff will fall apart in no time. ALL OF IT.

For glasses that will look right on you, check this post by Anisse Gross.


About Michael von Braithwaite

Does it look like I'd wear it on a boat, at an eccentric person's estate or accompanied by a peacock on a chain? Yeah, I'll probably buy that.


  1. blevit

    Love it. I know this transition stage well. I also I relate to the writers’ bodytype stuff. I have my overarching look, however, which I call ‘Modern Felicity Good’.

  2. Michael von Braithwaite

    THAT is an ADORABLE look!

  3. This is excellent advice! (Not just because you used me as an examp, which tickled me plum pink). And it is true that Macy’s has amazing deals on shoes. I went there the other day and bought 3 pairs for 75 bucks. Another thing I just got cued into in where you can get custom made dresses fit to your own special ass for UNDER 80 BUCKS! I hear nothing but good things about this. The time has come for custom made. No more Forever (2 wearings) 21.

  4. jennyjenny

    yeah i second eshakti! and actually lands end because with the nautical trend they’ve been kicking ass.

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