A fashion dm I couldn't answer.

Here's a thesis on Jenna Lyons instead.

Dec 20, 2024

A lady dm’d me recently about what to wear for a rare date night with her husband. She wanted ‘something fun’ that would cover her arms.

I started writing back my answer. Look for a plunging neckline to contrast with a full sleeve... but then I realised I was dolling out the kind of textbook advice you might’ve seen in a magazine 20 years ago. Something to do with proportions and the smoke-and-mirrors magic of ~concealing~ and ~revealing~.

So regrettably, I left her on read. I needed a bit more time to mull this one over.

I think we’re all still recovering from years of conditioning about what makes a woman “look sexy”. An LBD! A fitted waist! Red lipstick!

But what makes us feel really good, like confidently ourselves, is deeply personal.

This Zimmermann maxi is a great date night dress for me and happens to have sleeves. It has a bow around the neck but I wear it undone with lots of jewellery.

I started watching The Real Housewives of New York last year, for one reason only… Jenna Lyons. I’ve never dipped into the franchise before, so whoever came up with that casting tactic deserves a raise.

Previous to her big TV role we only got to absorb Jenna’s outfits through glimpses of her streetstyle, the occasional interview or media appearance and some pretty clunky Instagram posts. So it feels like a rare privilege to take in the full extent of her personal style - the way she dresses for dinner with girlfriends, a day out with her son, or an editorial meeting at the Coveteur office.

Jenna Lyons' take on relaxed glamour. Images: Instagram.

While Jenna is pretty quirky and self-deprecating when it comes to her personality, she’s a woman who strikes me as completely at ease with her sexuality - and it comes through in how she wears clothes. A shirt unbuttoned all the way down to her pants, with stacked diamond necklaces and her hair slicked back. A completely sheer sparkling tunic over a bikini-bra with silky pants. A pinstripe business suit. A grey cashmere jumper when everyone else is in cocktail dresses. She is relaxed glamour personified.

Last year the former fashion executive wore jeans on the RHONY reunion show and it made headlines. She did her very cool take on “glammed up” denim and people lost their minds. It was ironic, because in her time as President of J-Crew, she was known as “the woman who dresses America.” But America wasn’t ready for a Housewife in jeans.

In response to the backlash - to the pressure to wear a gown - she simply said: “it’s not me”.

I think we all need to be more like Jenna. Not a hot take at all, the woman has been a fashion icon for over a decade and routinely tops best dressed lists. But it’s because her approach feels so innate to her. So true to her own codes.

In the past few years, I’ve completely drained my wardrobe of pieces that “show off” or cling to my figure. The realisation finally landed that whenever I wore those outfits, I was dressing for someone else’s gaze… and never left the house feeling comfortable. When I really leaned in to what actually feels good, my style started making sense. I wanted to rewind the clock on all those occasions where I felt weird in my clothes and put myself in something different.

I once asked my husband for his thoughts on my more conservative approach to dressing up - that I always go for a long dress, or a voluminous sleeve or loose pants. I remember he said it would be weird if I wore something plunging or super leggy; that’s just me.

But again. That’s just me.

So what should you wear for date night, lady who dm’d me and probably didn’t expect a full dissertation on the subject?

There is no short answer for this. Honestly, there are infinite variables that could land you at countless different options. It depends on the date location. It depends how you feel on the day. It depends if you’ll be standing up or sitting. Inside or outdoors. What the weather’s doing. So the thing that really should guide you is instinct.

Last night I went to Sydney for drinks with my friend who’s just made a brief return home after moving to New York. I took two outfits in my car: a red sleeveless dress, and a bandana-print two-piece set. I had every intention of wearing the dress, but I took the set as back-up. Always gotta have options in case you change your mind, right?!

So when it got down to it, I put the dress on and did my hair and make-up, and it just didn’t feel right. I felt hot and itchy. It wasn’t giving off what I thought it would in my head, what I’d planned the whole car ride there. I was so relieved I packed the two-piece - and I felt truly at-ease with myself and my outfit when I walked into the bar.

And I was having such a nice time that I only took this terrible blurry selfie as evidence. The set is old Vrg Grl.

So ask yourself the question: what makes me feel confident?

Is it a printed maxidress and chunky sandals? Is it your straight-leg blue jeans with a great blouse? Is it a minidress with sneakers?

Start there, and I really believe your hotness will shine through.

Psst! For more fashion waffling, catch me on Nothing To Wear this week chatting to Leigh Campbell about what’s trending this second. I get really in my feels about jorts and discuss the return of your favourite millennial Brit girls. You can listen below!