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What To Wear To Dinner
The question I get the most. How to get dressed up when NOT going to work or a wedding. This week, finding our way back to just looking nice.
The question I get most often lately, surprisingly (not surprisingly?), from both clients and readers is “What should I wear to dinner?” It’s a less defined category, lost between WFH, WFOffice, sweats and proper cocktail. And I’m sorry, but I never really bought the whole “from day to night” thing. It’s become droll marketing copy and the idea of having to wear a work dress on a Friday night makes me cringe a little.
The more I think about it, the harder I find this question to answer. Increased socializing + a change in seasons is making this need feel more urgent, or so I hear in your requests. Plus, I’m dragging my friends to my 20 year high school reunion next week so timing is perfect for me to figure out WHAT TO WEAR!
I started thinking about the classic going out to dinner formula: jeans and a top. As I navigated the internet, I realized we are going about this all wrong. Even if we did still want to lean in to the jeans/top combo, designers are just not committed to the going out top the way they were in the early aughts. So the search for tops in general is extremely frustrating. I’m talking tops, not button down shirts, not knits, but the elusive TOP. So lets just not!
What makes a going out outfit special these days instead? Prioritizing another element of your look as the hero. It will make shopping easier and a lot more fun at the very least since there are way better shoes, skirts, pants and jewelry options out there. And it will also help you build a more dynamic wardrobe.
Here are four ideas (and one top that deserved a shoutout for actor in a supporting role) that change the focus for a night out.
Swap your statement
Focus on pants and skirts for pattern, unique shapes and color, and let your top fade to the background. I love hunting a printed Prada mini on TRR and pants in bright colors (hi High Sport!) Throw on your fancy t-shirt, a men’s button down sleeves rolled up or a buttoned-up-cardigan-turned-top and feel extra extra. Before you say, “but I’m a size 12,” this is a strategy I’ve been putting to work on a range of my private styling clients from size 2-14. If color or pattern scares you, try an A-line shape or a shirt that covers your bum to ease in.
This is something I’ve taken as gospel from years of googling and dissecting Miuccia Prada’s personal style. She loves a super high heel, especially in gold or silver. But basically she is always wearing a cashmere sweater with white t-shirt peeking through, casual and fabulous. So wear your jeans or menswear trousers or LBD as usual, but swap out your loafers/pumps/basic heels for something a little more alive.
A long shirtdress, but make it a shirt
Ok so I don’t own this. But that doesn’t mean I don’t have opinions. If you are going to experiment with wearing your shirt dress as a shirt, make sure its simple and slinky enough to hang nicely and not compete with the pants. You are already trying an expert move, so don’t fuss it up with a weird sleeve or something that has gathers and won’t hang right. (Exception: this beautiful Peter Do pleated shirt dress - it’s wide enough that it will still hang well and flow when you walk.) Now, when you layer these two, I recommend keeping the bottom buttons of said dress open to the waist of your pants so when you walk or sit it falls to the side and doesn’t bunch or become something you need to adjust. To see even more advanced moves on styling a dress over trousers, see my friend Leandra’s newsletter last week.
Black Jacket, Gold Buttons
You know the person that you think about when getting dressed, like would I feel confident if I ran into this person in this outfit? We all have them…a former boss, former boyfriend, impossibly stylish fashion role model…
Whenever I wear this jacket, I feel like I’d be ok with running into any and all of those people. It’s a look that seems to always say: ‘star of my own life.’ The curse of French girl chic. Will we ever escape it? Probably not, so leaning into this jacket. Sophisticated with black jeans. Vintage vibes with white or light blue. And a great layer over your favorite slinky dress that you would never wear bare (or maybe you would?)
Below, my dream Celine jacket and the best comparable option I’ve found so far, from French high street brand Gerard Darel (far right). If you have a little more patience, I recommend scoping out a vintage jacket with plain buttons and adding your own brass from Etsy, voila!
A really lovely top, for basically every body type
And for the fifth point today, I’m not going to give you another idea, but a really beautiful simple top that one of my clients just bought. It seemed to solve a lot of problems. It's not exciting, but it is very easy to wear. Falls nicely on the arm (for all you no-sleeveless people), not fussy on the bust and neckline (good for basically any bra size!) and comfortable at the waist. Tucked in, it would look good under a jacket too. And its easy to pile jewelry over. So here you go, just a little something that might take the stress out of creating a look with all the statement items above.
Hope today’s edition will prevent you from throwing your entire closet on your bed every time you have a dinner reservation this fall!
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