Save. Spend. Splurge.

To dress up or not to dress up?

I am facing a bit of a problem at work right now, style-wise.

Not only did my pants not fit (it was obscene), they are also no longer a comfortable rise (mid, when I now need/want high), my skirts all fit kind of awkwardly now, I feel like my tops are not quite right for the new, looser, baggier pants I bought, and to top it all off, my work environment is more casual than business.

Like, CASUAL with all-caps lettering!

What happened!?“, I shriek internally..

Let’s start with the fit issues.


So now that I only really feel good in high-rise pants, I realize a little late that all my work pants are mid-rise. Welp, there goes all of my staples out of the window.

I really just don’t feel comfortable wearing mid-rise. It creates a muffin top where THERE ISN’T one, and I will say this for any woman as much as for myself:

If you see muffin tops, and you feel like it isn’t comfortable, it means you either need to go up a size, or go up in the rise.

(That should be put on a metal sign and hung in every dressing room.)

My personal comfort level has changed. I used to be okay with mid-rise pants, maybe a little muffin toppage hapening here and there, but now it is something I am acutely conscious of, this little belly hanging out over the waistband, jiggling hello when it should be tucked underneath and incognito.

I am not fat. I know this. I am just uncomfortable with certain cuts now (a sleeve that grips my arms and turns them into sausage links is also out.)


In hindsight, not such a great idea. I should have left an inch or so for give, but I basically had it all to fit my (then) raw vegan body that was at 110 lbs, and now I am around 123 lbs (based on what my doctor told me), with a little extra poundage in new places where it previously stayed away from (hips, butt, thighs).

I don’t hate this new body, I just hate that I can’t fit back into my pretty things.

For the future — do not tailor everything to an inch! 😛



I now have a little more poundage around my butt and my hips. I have wanted this for years so that my butt isn’t so flat and skinny, but now that I have it, my tailored pieces (see above) don’t fit right.


It’s not a bad problem, but I can 100% pinpoint to it being now about 3 – 5 pounds put on in the past year, making my clothes hang all wrong.

So what to do?

Do I lose the little bit of poundage and fit back into my gorgeous tailored pieces? I am leaning towards this option because let’s face it, I LOVE what I have in my closet. I have spent years curating each piece and it’s all stuff I enjoy wearing.

Or do I embrace this new, curvy-to-me shape and get a new wardrobe, spend time, and spend MORE $$$ (I am actually crying at this option, oh my how the times have changed)…!?!?


I am talking people in sandals with t-shirts, casual. I had to downgrade from wearing my beloved heels which make me feel tall, confident and like an Amazon, to wearing flats.

Cute flats, but FLATS. I feel so short, especially amongst a sea of men.

I also have only silk blouses and fancy attire. That’s just what I like to wear to work. Unfortunately, this REALLY stands out in a sea of men, all dress haphazardly and casually.

I have taken my cue from the managers however, and they’re all in button-up shirts, and trousers, no jackets or ties. This screams business casual to me, so therefore I shall dress accordingly.

The only other woman in the office is a Vice-President who wears heels and suits to work no matter what. I can’t pretend I’m on her level.
As a result, I’m sort of scrambling to find outfits each day that are still outfits I deem work appropriate but are also not too formal or stylish for an IT department that thinks wearing a sweater is formal attire.

I’m looking at my wardrobe each day and basically wearing the same items week after week with different jewellery.

The good news is that I’m creating new outfits I never would have worn before and my preference has since geared towards wearing less feminine, girly colours and prints and sticking to plain neutrals with stripes. I don’t feel like I have the liberty to wear bright prints or colours to work as I would REALLY stand out.

I have also been shy wearing brighter prints and colours because being pretty much the only woman there, you can imagine that this really stands out in a kaleidoscope of brown, black, blue and grey.

Magenta Pink?


Deep rich purples?

All major favourites, but all very bright colours that spotlight who I am at any given moment.

I’m also wearing more dresses and skirts but in a casual manner and trying to be cognizant of how much leg or chest I might be flashing (not that any of what I own is very short or low cut to begin with).

I’ve found wearing a tank top or a bandeau to ensure that if my top gapes open, I’m not flashing anyone has been a real sanity saver and I’m pleased I thought ahead and bought a few of those in various colours to cover up without having to wear another shirt underneath.

Aside from that, I can’t think of anything else I can do, taking into account my jewellery has to be low key as well, as I got some comments about a huge cocktail ring I wore the other day.

Frustrating but also a nice change of pace I must say.

I only I wish there were more women, and more MY AGE in the office!


*sigh* Blame it on the democracy of office wear, but people are just super dressed down these days. I can’t even believe that open-toed sandals are appropriate in the office.

I still find it very weird to show your toes and yet that is all I see all day long from men in flip flops.

Anyway, that’s my dilemma right now.


  • Tania

    I used to have my clothes fairly tailored with little room to spare (to look my best according to my body type advice) when I was in my 20s and 30s. Then my weight would go up and back down. But what I found is that with each fluctuation my body would not return to an exact version of itself. Same weight, different size but slightly different body. So I have less tailored items now (but I’m not casual, I wear dresses nearly every day – but not Wall Street either). Just have clothes with a bit more give now and dresses. Btw I think you look wonderful.

  • Anne

    At my previous job I had the second highest position and the dress code was business casual, even casual. I had some employees that were really in to clothes and dressing a lot more fancier than I did. I was wondering if I should dress up as well, especially when we met people outside of our organisation, but decided against so that the others wouldn’t feel obliged to dress up as well. I didn’t feel it was wrong of my employees to dress better than I did, on the contrary, it was a pleasure to observe their outfits of the day.

  • Marthe

    lose the extra pounds

  • Revanche @ A Gai Shan Life

    I love the idea of bandeau tops but I need some that are really easy to put on. I hate dislocating my shoulders or wrists or whatever trying to get things like that on!

    I THINK you’re doing all that you can, already, and that’s likely good enough.

  • hopeczl

    You probably wouldn’t like working in Vancouver then. West Coast is super casual, especially in IT, and I struggle with this as well. My workplace is very similar to yours and with the same dilemmas. I decided to wear what I like but pay attention to director, VP level – cannot be dressed better than them.

    • Sherry of Save. Spend. Splurge.

      It is hard, isn’t it? 🙁 No heels for me, only flats, I have to try and not be so conspicuous with “expensive” looking items.. although some of my most casual looking pieces are VERY expensive they just don’t know it as it isn’t branded…

  • liteadventurer

    Guy here. I think people dress down simply because they can, especially in certain professions. It’s just easier to wear your normal everyday clothes. I’d love to dress more casually for work, but no one would ever take me seriously. A tie adds about 5 years to my appearance and gives me more street cred.

    • Sherry of Save. Spend. Splurge.

      This is why you won’t catch me in short skirts, low cut tops, too high heels, or anything that would be too hipster-ish at the office even on Casual Fridays. That, and I am not saying a word of how old I really am.

  • Cassie

    Oh, I hear you on this one. I was actually excited to get dressed back up for work again, because it was definitely business casual when I went on mat leave, but they’ve relaxed a lot in the time I was gone. It’s not unusual for my boss to wear a t-shirt and hoodie on Friday, and as long as we’re not sloppy we’re not being held to the company dress code anymore. I look out of place if I dress up! Though to be perfectly honest, I still wear heels if I feel like it. I’m 5’2″, and a lot of the guys I work with are closer to 6’2″. I’d love to see some of your more casual outfit ideas!

    • Sherry of Save. Spend. Splurge.

      Haha “casual outfit” just means jeans and a top these days and some fancy flats… Honestly, “casual” isn’t really in my vocab but I’ll try 😉

      I’d wear heels but I click too much in them where I work, and it is VERY noticeable as the only other woman who wears heels is a VP.

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