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Why I’m Over Over-Dressing

Posted on 5 Comments Location: 7 min read

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his week marks the start of our 10 day countdown to our Florida vacation – which means that, in between worrying about how we’ll survive an 8-hour flight with a toddler (And worrying even more about how we’ll survive the toddler jetlag at the other end…), I’ve been spending a lot of time thinking about what the hell I’m going to wear on holiday.

This has actually proven to be a much trickier question to answer than would normally be the case. You see, I’ve always LOVED summer fashion: in fact, it’s my favourite season to dress for by far, mostly because it’s just so easy. I love the fact that, when the weather’s warm, I can wear whatever I want to wear, without having to worry about tights and coats and scarves and the like. I love the fact that I can break out all of my favourite dresses and skirts again, after a winter spent almost exclusively in jeans. Most of all, though, I’ve always loved summer holiday dressing in particular, because – for me, at least – it’s the perfect excuse to get dressed up. 

Now, if you’ve been following this blog for a while now, you’ll already know that over-dressing is kind of my thing – or, at least, it was. I’ve spent most of my adult life complaining to anyone who’ll listen that there just aren’t enough opportunities to dress up any more, and fielding questions about whether or not I’m off to a wedding later – because,  until recently, that would have been the only real reason behind whatever I happened to be wearing at the time.

over-dressing is kind of my thing – or, at least, it was.

“Ooh, lookit you, all dresssed up!” people would exclaim as I passed. “Where are you off to, then?” And, honestly? It would probably just be the post office. Or the mall, to buy even MOAR ridiculously inappropriate outfits. One time our neighbour asked me what I was up to when I was out walking the dog, and I was so confused, because, well, I was walking the dog? The dog I have here with me? The one I’m currently walking? It was only as I walked away that I realised I wasn’t the only one who was confused: because I was out walking my dog in a 50s-inspired prom dress and bright red lipstick, and my neighbour was probably wondering where on earth I was taking him. OK, I’d thrown on a pair of flats, as my only concession to practicality, but no matter how fond I was of telling people that flats were a great way to “dress down” an outfit, the fact remained: I legit looked like I was going to a wedding or something. But with a dog. No wonder the poor guy was confused…

At the time, of course, I didn’t really think about it like that. I knew I was hopelessly over-dressed most of the time, obviously, but I’d have defended that decision to the death, telling anyone who asked that this was how I wanted to dress, and nothing was going to stop me – least of all the fact that I have the kind of life which contains absolutely no opportunities to dress up. Like, EVER. 

I wasn’t going to let that stop me, though: I wanted to wear prom dresses and pencil skirts, and a different pair of stilettos every day – so I did. And, of course, there’s absolutely nothing wrong with that, is there? People SHOULD be able to wear whatever they like: so if you’re a fellow over-dresser – or an under-dresser, or a whatever-the-hell-you-like-dresser – I’ll defend YOUR decision to the death, too. (I mean, I probably won’t, tbh. Not TO THE DEATH, anyway. I mean, I’ll think it’s pretty cool that you’re doing your thing, without worrying about all of the Judgy McJudgypants out there, but I draw the line at dying for someone else’s prom dress or whatever. You keep doing you, though!) It’s just… I don’t want to do it myself, any more. Over-dress, I mean. Because, somewhere along the line, I realised I’m just over it. I’m over over-dressing – and I don’t really see that changing any time soon. 

 
Of course, it’s really tempting to blame parenthood for this, just like I blame it for everything else these days. While parenthood may be the reason for as lot of the changes in my life right now, though, it’s only partly to blame for this one, because, the fact is, I’d been falling out of love with my wardrobe since long before Max was born. I think I just reached a stage where I got tired of it all, you know? I was tired of wearing clothes I had to worry about creasing or ruining, and tired of being constantly cold and uncomfortable, because I’d always go for the outfit that looked best rather than the one that would actually be suitable for whatever I was doing that day. I was tired of having to keep on explaining myself, and why I was dressed the way I was – and then inevitably feeling a little bit looked down upon for it: judged as silly and frivolous, just because I liked high heels and pretty dresses, and had decided to wear them to a place where everyone else was in jeans.
 
(Are you getting that I was tired, here? Because I’m just not sure I’ve made that clear enough yet? I do know I’m tired of this paragraph, though, so let’s try to move it along, shall we?)
 
I can’t deny that having a toddler in my life gives me even less inclination to want to dress up right now
Most of all, though I was just tired of the clothes themselves. All of those retro-inspired looks I used to love so much suddenly started to feel costumey and fussy to me, and I just didn’t want to wear them any more. Instead, over the last few months, I’ve found myself more or less adopting a capsule wardrobe of basics: I still have tons of clothes, but there’s just one rail in my wardrobe that I usually dress from, and the clothes on that rail are on constant repeat. And while I’m pretty sure this would have happened whether I’d become a mum or not, I can’t deny that having a toddler in my life gives me even less inclination to want to dress up right now. Can you even imagine trying to navigate soft play in a pencil skirt, for instance? Or sitting cross-legged on the floor at Bookbug, wearing a 50s-style skirt, complete with petticoat? I can’t. The old me would totally have tried to do something like that, though – or would, at the very least, have felt totally aggrieved to be having to wear something practical rather than pretty. 
 
 
 
The new me, though -the me I am now – knows she’s going to be spending a large part of her day crawling around on the floor and/or wrestling with an excited toddler, and she’s not going to do that in her best dress, you know? So, jeans it is: or, now that the weather’s finally starting to warm up again, maybe some casual skirts or dresses if she’s feeling particularly fancy. 
 
Which brings me to my upcoming trip, and the difficulty I’ve been having packing for it. Not because of the trip itself, I hasten to add: I mean, I’ve visited Florida more times than I can remember, so it’s not like I don’t know what to expect in terms of weather, activities, etc. No, this trip is problematic for me purely because when I looked at my summer clothes, I realised there was hardly anything I was actually excited to wear. Everything I tried felt costumey and wrong, and just definitively NOT ME any more, which meant I’ve basically had to start again from scratch. There are a few old favourites that somehow made the cut, but for the last few weeks I’ve been doing my best to build myself an all-new summer wardrobe. I’m not totally sure I’ve succeeded with this, to be totally honest – mostly because, when I looked at my dress rail earlier this week, filled with all of the clothes I’ll (probably) be taking with me, I realised I’ve basically just bought the same polka dot dress in a variety of different colours. WHOOPS. 
 
(Oh yeah: my style may have changed, but my love of polka dots has not. Not even a little bit…)
 
All of a sudden, dressing for a holiday is difficult. With my usual jeans and sweaters out of the running, I’ve been really struggling to find clothes I like just as much, but which will be suitable for the very different temperatures I’ll (hopefully) be finding myself in. So, I have a horrible feeling I’ve failed in my mission, and am going to go on holiday next week and STILL feel over-dressed and uncomfortable, despite my best efforts to avoid it. I guess there’s only one way to find out though: and, as I know only too well, if the worst comes to the worst, and it turns out I HAVE messed up with the holiday packing, at least I’m going to a place with a LOT of shops…
 
red hair and green dress
 
 
I’m Wearing: 
 
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5 Comments
  • Heather
    May 6, 2019

    Thank you for writing this post! This is everything I’ve been feeling since my son was born six months ago. I used to be in dresses and heels all the time. Now I live in jumpers and jeans, which feels so alien. It’s like I just cant be bothered with dresses right now, and so little of my vintage repro wardrobe is breastfeeding friendly. Your post has made me feel a little less lazy and a little less alone.

  • Veronica
    May 6, 2019

    I think that tshirt dresses and espadrilles are the answer. You could also try some linen pants with stripey shirts, or a bodysuit to balance out wider legged linen pants.

  • Louise
    May 8, 2019

    I totally get this, but I veer between wanting to wear more practical clothes then having the odd inner rebellion where I want to wear a crazy OTT dress and dress little Miss to match. I definitely feel myself going down a sleeker and less fussy route though. Great post x

  • Ashley A Hutchinson
    May 13, 2019

    I could not adore this post more Amber. I feel the exact same way. Why is my closet so disappointing? And why — even without a toddler in tow — do I suddenly just want to be comfortable? I used to love uncomfortable outfits because I always felt so put together. Now I can hardly stand to wear tights…

    Love that you’re experiencing the same thing and cannot wait to see where your wardrobe evolution takes you next!

    Xoxo,

    Ashley

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