Decluttering - should small clothes stay or go?

This was exactly what I found - I left the office to go on holiday in March 2020 and didn't step back through the door until Spring 2023 (lockdown, WFH and then maternity leave). When I came back, office dressing had completely changed - our office was previously business formal, so lots of LK Bennett and Hobbs shift dresses with sheer tights and heels every day. Now smart jeans and trainers are standard fare and I'd look like a out-of-date throwback if I rocked up in a suit and stilettos. 95% of the office wear which I packed up in Summer 2020 has gone on Vinted.

Why on earth would someone not be comfortable with that?

I've literally JUST thrown away my small clothes. I've been kidding myself for 5 years that I'd slim back into them. Ironically, I have just started exercising seriously over the past few months, but even so, my old clothes were very small, like 3 sizes too small.

I came to the conclusion that if and when I get down to that size again, I'll buy new clothes as a reward for getting there.

I've kept some things and got rid of others. Now nearly 3 stone down from my highest weight and missing the things I gave away! But I don't really do things that are either in or out if fashion so the age of my wardrobe is irrelevant to me really.

Keep your favourites and ones that remind you of times gone bye ditched the rest. I have dresses that no longer fit and haven't fit for a long time a few skirts but the rest goes when i stop feeling good wearing it.

If you did keep them, would you be comfortable still wearing them if photographs were taken and someone were to say to you something like 'oh that's the dress you wore to my sons 21st birthday 8 years ago?' If not, then get rid of them.

I’ve just lost 3 stone and am glad I didn’t chuck out the clothes I’d kept to slim into, as it would be costing me a fortune now.

What an unhealthy mindset.

OP - get rid of the clothes. When you go back to work, you will want different clothes. As people have said, work culture has changed and people (even in finance and law) wear more casual clothes now. You can always buy off Vinted if you don’t want to waste money.

Keep them! Getting rid of old smaller clothes is like admitting to yourself you'll never be that size again. There's absolutely no reason you can't be, and if you do choose to lose the weight you'll be glad you don't need to spend on a whole new wardrobe again. There's nothing nicer than trying on your old clothes and realising not only do they fit now, they're baggy!

I've given myself a year under your circumstances. Then everything goes. Clothes don't always store well.

I have been a size 6/8 three times in my life. Aged 19 pre DC. Age 30-42 after three DC. Age 52 post menopause. Still that size now Age 55. In between I've been up to a size 14. My small clothes have been up and down from the loft like a fiddlers elbow. Because the weight and size I am depends my diet and excercise not my age or life stage. If you're happy at your current size and have no wish to return to smaller get rid. If you think one say you'd prefer to lose weight, hang on.

Don't look - what's in the box?!

If you can name 4 things and why you want to keep them, keep it.

Lose the weight and the clothes.

At best, they will fit but are dated. Office wear has changed significantly over the last 5 years. So unless you were very forward thinking in your dress sence, you'll likely look like you've just woken up from a coma if you start wearing it again.

Are you thinking of practicalities?
To avoid shopping once you can wear them again?
Or are you thinking of identity?
Surely you have changed int he last 5 years so your style is not the same?

Get rid. Really.

I guess then you're going to have to choose between which is worse: shopping or moving a box around that reminds you of your failed attempts to lose weight every time you look at it (and probably shopping anyway when you inevitably don't like any of the clothes in it any more).

I'm not a shopping fan either but I am currently very fat and it's much less bad in the thin part of the yoyo.

You've got exactly one year and one week to fit into the clothes. If they don't fit once you're back in the office you'll have your answer!

One size smaller is nothing, it's a bit of non-bloat and some compression pants, I'd keep them. Especially as you're already on track with losing weight (go you!)

My weight yo yos, if I ditched my wardrobe every time I gained or lost a size I'd have spent tens of thousands, and contributed god knows how much to landfill and crappy fashion trade practices.

Just saw you hate shopping... Even so ... clothes from the loft - No.
But keep the faith and keep going.

If you think you would still wear the clothes to work if they would fit I would keep them until you start work. It’s only another year. Just make sure you really would wear them. I realised I had kept things that were washed out and although I might have carried on wearing them, I wouldn’t restart after a break.

Neither.
Get rid of the clothes but keep the faith.
Keep some money aside for a new wardrobe when you lose weight.
Let that be your motivation rather than clothes that have been in the loft for five years already.