What To Wear For An Evening Out

Using what you already have hanging in your wardrobe...

In the comments of my April Style Clinic post the top comment came from Chelsea…

“Hi Anna, I’m never sure what to wear for dressier evening events. What’s the equivalent of “jeans and a going out top” nowadays for 30-somethings?”

With 30 likes on the comment, it’s obviously a conundrum a lot of us have!!! And I had thoughts!! Too many in fact to put into a single reply, so Chelsea (and the other 30 comment likers) - this one goes out to you. Here are five outfit formulas that I’d pull out of the bag for evening social activities, albeit once the weather warms up a little (although I’d just throw a trench or blazer over any of the following outfits if I needed to).

Just a general note that I observed when putting this together. A lot can be done with shoes and bags. Seeing as my style tends to lead a little more casual these days anyway, I could easily pair flip-flops and a giant tote with four of five of these looks and they’d work just as well for the daytime as they do for the PM. So don’t feel like your base outfit needs to be the star of the show. Allow the accessories to do the work. They can handle it!!

Outfit linked here*

Button-down shirt + long straight-leg trousers + strap sandals + structured bag + statement necklace & earrings. The scenarios I had in mind here were ‘sexy drinks’ or a ‘nice dinner with friends’. Nothing fancy fancy, but just something that you want to feel more elevated for. The secret sauce boils down to three factors: a chic-looking strap sandal (that bit of heel gives some extra height to things), wearing both a statement necklace and earring jazzes up what is otherwise a plain outfit and unbuttoning the shirt - like how low can you go?! Also, a structured bag gives some balance to the looser linen top. Fancy shoes and fancy bag + chill trousers and shirt - it’s a good combo.

Outfit linked here*

Linen waistcoat + midi silky shirt + strap sandals + dinky bag. Ok, here I was thinking of finding an outfit in my wardrobe for more of a chill garden party, drinks outside, Aperol spritz in hand. Here’s what I’d want to be wearing for that!!! It’s so much more feminine than what I usually go for - but sometimes that’s nice you know? Plus I could always add a bit of shape with a blazer or trench over the top if I wanted to, but I fancied something cute. If you wanted to go dressier then you could go for a contrasting sandal or a waistcoat made of a heavier, more fitted fabric, but I like the addition of structure in the form of this boxy bag (sourced from The Hosta btw).

Outfit linked here*

Oversized shirt + comfortable wide-leg jeans + heels + the fanciest bag that you own. My thought process was ‘outfit for when you need to leave the house after 7 pm but you’re ovulating/on your period’. You get it. You feel bloated. You just want to sit under a heavy blanket and soothe your soul with reality TV, but you’re needed elsewhere. So here’s what I’d propose. The comfiest pair of jeans that you own in a style that’s wide on the leg but not necessarily flared, an oversized shirt rolled at the sleeves and un-buttoned to reveal a bit of skin and the fanciest bag that you own just to tie it all together in a big ol’ bow. It’s the essence of Tibi’s ‘Big, Slim, Skin’ theory - something big, with something slim (the trousers-ish in this case) and a bit of skin thanks to the sleeve roll-up.

Outfit linked here*

Oversized blazer + wide-leg silky trousers + strap sandals + fun bag. Ok, this one feels like a bit of a wildcard because it’s easily the dressiest look out of the three. But Claudia did use the phrase ‘dressier evening events’ in her original question and I thought it was good to have a formula in your toolkit for a fancier occasion - I’m thinking like a semi-formal work thing? I’d happily wear this to an evening event in London. But there is another use for this outfit. You know when you’re heading somewhere and you have NO IDEA what you’re about to walk into? Maybe it’s your partner’s after-work function, or an invite where you just can’t decipher how dressy you’ll need to be? This would be my go-to. Throw on a bandeau, or vest, or slim-fitting linen top under your blazer and if you get to your destination and feel too stuffy in your blazer just shed it and underneath you’ll reveal a chilled silk trouser and linen top combo.

Outfit linked here*

Fitted waistcoat + kick flare trousers or jeans + ballet flats + textured bag. For my final assignment, I gave myself the brief of ‘what would I like to wear out tonight (just if it was 10 degrees warmer)’ - and this was the result. Perhaps my favourite from the five?? If like me you’re hoarding every waistcoat/knitted vest you can find, here is a good way to wear your more form-fitting versions. A kick-flare trouser mirrors the shape and adding a textured bag gives some interest. I also wanted to show that a night-out look doesn’t have to have heels!!! A shoe option that’s slim and simple and shows off a bit of foot works just as well.

So thank you to Claudia for being the spark for this post. Even if you have no current evening out plans *raises hand*, it’s a nice experiment to do every once in a while, if not seasonally, just so that next time a plan comes up you have your own little lookbook to browse. Feel free to borrow and tweak these formulas as you wish - I hope they come in handy!

Anna x