What to Wear: Ex-, Current & Future Boss?! (ETA: Possible Contenders + Final Outfit) - YouLookFab Forum

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What to Wear: Ex-, Current & Future Boss?! (ETA: Possible Contenders + Final Outfit)

Zaeobi

(website)

Veteran

ETA: I finally settled on the reddish orange dress with my flatform sandals & chocolate rainbow earrings (attached). Thank you so much for everyone's suggestions!

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Just realised how sticky this situation is to dress for...

So my ex-boss is leaving HK with a low-key bar drop-in for her farewell do this Friday. She's fairly laid-back, was at my wedding. Sounds casual, right?

Well, she's friends with my current boss (for whom I'm working part-time), & also a potential future boss (have spoken about possible vacancies over the phone but have not yet met), who will both also be there. Oh, & other colleagues/ acquaintances from my soon-to-be-ex workplace (ex-boss works at the same centre where I'm currently wrapping up my contract) will likely also be dropping in at some point (don't know when).

What on earth do I wear?! I don't want to be too stodgy at a bar, but at the same time I also don't want to give the wrong impression to a potential employer. I was thinking of perhaps wearing my satin cargo pants, but with what? I do also need to be somewhat practical (possibility of both rain & high humidity, plus uphill urban walking)...

Any suggestions would be highly appreciated!

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42 replies

Latest reply was from rachylou

Angie

(website)

Fashion Stylist

You could wear one of your pretty dresses with relaxed shoes, and a fun topper (or scarf) for arctic HK air-conditioning. Pretty hair up or down

bella

(website)

Veteran

Since so many work colleagues are involved, I would treat it as a work day actually. I'd wear what I would normally wear on a not-too-casual work day, but most importantly behave the way I would at work.

Suz

(website)

Veteran

What time is the drop - in? Immediately after working hours, or later? That might influence how I'd dress -- if immediately afterwards, I'd dress as I might for work, but if later, I'd be more flexible.

If you wore the cargo pants do you have a lightweight jacket type article -- not necessarily a blazer, but blazer-like? Like a linen moto or something?

Roberta

Veteran

Argh, stressful! I would think "adjacent" to whatever your workplace vibe is - not a blazer, but a light/cropped sweater over a dress with more casual shoes (as Angie suggested). Or the satin cargo pants with a print bomber jacket?

Ha, I see I am only suggesting what wiser minds already have. Take whatever you normally wear to work and exchange a couple of things for more casual or more whimsical items. Including jewelery and a bag.

Good luck!

rachylou

Veteran

I think like Bella, I’d also treat the occasion as an ‘after work’ thing. Dressed for work, but maybe let the hair down so to speak.

Janet

(website)

Veteran

I agree with Bella — dress like you’re dressing for work, with a “happy hour” afterwards.

Jenni NZ

Veteran

Great advice so far. I can’t imagine you being stodgy.
I would always personally err on the side of being slightly more dressed up, but not sure if you would.

Stagiaire Fash

Veteran

This sounds like a higher stress version of an activism/academia thing I went to last week.

Take your cue from the venue/event, not the people who will be there. They will see that you can adapt and fit whatever the requirements are. What really matters is that you’re there and you have at least a brief conversation with each of them. Mho anyway.

chewyspaghetti

Veteran

I would wear whatever you would normally wear for this type of event. You dress modestly, if I recall correctly, so you should be ok.

Zaeobi

(website)

Veteran

@Angie
Hmm a dress could work, now that you mention it... maybe one that hits at ankle length instead of too long?

@Bella @rachylou @Janet
Good point - I'm often criticised for coming across as too 'serious' or 'intense' when people first meet me (especially in the workplace), so I'm just worried that bringing that same energy to a casual 'happy hour' gathering might backfire? Especially in an industry where being personable & approachable is important (of course I am this way with my students, but the irony is that other people often don't know this unless they observe one of my classes lol...)

@Suz Think it'll start after work then go on late, people can come & go as they please - I'm planning on dropping in straight after work then dipping before people get too 'sloshed' (as they put it, lol).
My non-blazer toppers consist of a dark brown leather jacket, a 3/4 sleeved orange cropped jacket & a dark brown, soft (jersey) peplum jacket. Any of that sound suitable? None are particularly lightweight, but I could perhaps sling it over my arm if it gets too hot? Or maybe I wrap a shawl around myself instead, as @Angie suggests? I'll be WFH teaching before I head out, so a topper might not be a bad idea since I'll likely be wearing one for Zoom anyway, hmm...

@roberta
Good call on the jewellery & bag! Maybe a statement necklace could help? Also a lightweight cropped cardigan I absolutely could do - why didn't I think of that when @Suz mentioned toppers?? Lol can you tell I don't have the mental bandwidth for any of this right now?

@Jenni NZ
Thanks I think my issue is that teaching is a fairly casual & practical industry (I've seen people wear 'nice' jeans to work), but the 'higher ed' aspect of it means that really differs across personalities (at my ex-boss' centre, I've seen men wearing everything from collared shirts to cargo shorts to teach). Current boss' work is in corporate teaching, though I've seen him in floral shirts (in dark colours & a small print, but still)! So judging what counts as 'slightly' dressed up in this context is hard, lol!

@StagiareFash
Good point - I guess I'm also at a loss because 'hanging out at a bar' is unusual for me, so wouldn't know how to dress for that under normal circumstances either haha! That's why I thought the satin cargo pants might bridge the gap between 'going out' & modestly covered-up 'dressy'. Not sure they'd count as 'work appropriate' though... but maybe that would be a good way to show adaptability instead? Hmm...

@chewyspaghetti
True, I usually prefer to dress modestly - which comes in handy at work! But I'm just worried that can come across as stodgy when at a bar (see my replies to @Bella & @Stag above).

Sal

Veteran

I like the sound of the satin cargo pants....

If I was in that situation I would choose a blazer and jeans, or something that blended smart and casual in one outfit.

It is a tricky combination but I think erring on the smart work look maybe with one more casual aspect would work.

Zaeobi

(website)

Veteran

@Sal
'Smart with one casual aspect' is a good way to think about it! So if I *did* wear the satin cargo pants, you're saying it should probably be with a cropped cardigan/ blazer & flats (not the leather jacket & combat boots), lol?

To give some context, the forecast is currently showing Friday PM to be 28C with 83% humidity & a slight chance of rain... I'm going to take the MTR (public transport) then walk ~10-15 mins outside to get there. I'm currently thinking that trousers rather than a dress, but maybe combat boots would be better in the rain? Arghh so many factors to consider, how did I ever manage social events pre-COVID?

CarolS

Veteran

I like Sal's suggestion of 'one casual aspect'. I think the odds of you dressing in a way that will give a future boss the wrong impression are literally zero. They know it is a casual event and not a job interview. You will not Show up some midriff baring micro mini with half a dozen questionable tattoos showing. Rather, they will see you looking fab and casually polished - and they will see you are the kind of person who maintains positive relationships with past bosses and colleagues. Winner all around. Call it casual with a professional slant or professional with enough casual to be fu - either way, I'm confident you've got this!

Zaeobi

(website)

Veteran

Thank you everyone, for your quick input! Based on your suggestions, these are the choices I've narrowed it down to so far:

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Dresses:
1) B.Young deep orangey red 3/4 maxi dress: (maybe with combat boots?)
2) Mango marigold tank maxi: (w/ a topper)

Toppers:
3) Thrifted chocolate leather jacket: (worn open or half zipped up like this?)
4) Seasalt vanessa cardigan: (have a bunch of these, so you can suggest other colours!)
5) simple cotton top: (also have many of these, in 3/4 or long sleeved options)

Bottoms:
6) Parallel Lines satin cargo pants: (might be more practical for rain (can tuck in the pocket 'streamers' lol), but with which topper/ shoes? Combat boots = too much?)

Shoes:
7) FitFlop Heda sandals: (despite possible rain, these stay stable due to the platform)
8) FitFlop tassel dorsay loafers: (usually my go-to casual shoe, but too shiny?)
9) Blondo Mady boots: (they're waterproof! Could unobtrusively 'casualize' #1-2 above?)

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Feel free to chime in with what you think does(n't) work, or if I'm going in totally the wrong direction here? Lol...

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Bijou

Veteran

Wear what makes you feel great and confident. You want people to remember the person, not the outfit, so wearing what makes you feel comfortable and confident would always get my vote.

You really can't go wrong with any of the options you have put forward. That said, I really love the look of your orange dress and also the satin cargo pants which would be beautiful with a 3/4 sleeve tee.

As a topper either 3 or 4 is lovely and it depends upon how cold it is as to whether you need to warmth of a leather jacket or a lighter cardigan. As for shoes, your tassel loafers look very chic, but if it is extremely rainy, your boots are fab too!

Stagiaire Fash

Veteran

Carol and Bijou are on the mark. Your outfit can strike the right tone but once it’s set the scene, your positive, sincere, kind personality is what you want to be center stage.

28 is hot. How can you wear a leather jacket or boots in that weather?

Shiny shoes or sandals sound right for hanging out for drinks. I vote for the pants or the 3/4 sleeve dress, cause it might not need a topper.

Jenni NZ

Veteran

Reddish orange dress with gold loafers. And the cardigan in pic 4- either that colour or any other colour you feel tones in.

April

Veteran

Satin cargo pants? <swoon>

kkards

Veteran

Ok what are you doing for a handbag? Sorry to add another stress
For bar events/work happy hours I start there. Will this be a situation where I can leave my bag at the table (ie we have a private room or a section reserved for a large group) or will I need it with me at all times. If I need my bag at all times, then I need a light small crossbody.

Otherwise re What to wear, 100% with Bijou, wear what makes you feel great and confident

of ourse I’m partial to the stain cargo pants, but that’s me, and you need to do what’s right for you.

Stagiaire Fash

Veteran

Kkards, I know it’s just a typo, and I make plenty of them myself but still, “stain” had me thinking the party got pretty raucous!

kkards

Veteran

Stag thanks glad I would make you laugh. Going to leave the typo so others can appreciate it as well

Zaeobi

(website)

Veteran

@Stag you're right, 28C is too hot for a leather jacket - but you never know with A/C here! Might compromise with a cardi instead

@Bijou
Those are the two I'm leaning towards now - would the satin cargo pants look strange with a cropped cardigan, do you think?

@Jenni
Will try on the dress tomorrow & see - could be just the ticket for not having to faff around with a cardi/ scarf/ other layers!

@kkards
I'm thinking of wearing my teal belt bag - the one that converts to a crossbody or shoulder bag by adjusting the strap I was thinking of either my gold or olive knot bag, but handsfree trumps a wristlet when there are so many unknowns!

I'm partial to the 'stain' too (here's hoping that's not foreshadowing! haha) just because it's an 'in between' item that I don't get many opportunities to wear (not quite 'fancy party' but not 'casual weekend errands' either). Will try them & the orange-red dress with my map print scarf tomorrow, to decide once & for all! Thanks, ladies!

Joy

Veteran

Will satin cargo pants get soiled on the way on public transport or sweat in the heat and humidity? Will they get water spots? Either dress might be a safer cholce, dressed down with one of your cardigans.

Angie

(website)

Fashion Stylist

NICE! All fab! Can't go wrong with any of the options

You absolutely need to bring a topper for inside in Hong Kong. The air-con is relentless and freezing. I get it!

I vote orange dress, either topper, a necklace or scarf, and the gold shoes. If that strikes your mood on the day!

Zaeobi

(website)

Veteran

Good point, @Joy - although I suspect the lighting will be fairly dark at a bar that's set inside a now disused prison, so it's not likely anyone would be able to see much of my sartorial transgressions anyway lol...

@Angie Decisions decisions... Humidity is now up to 92% with a 42% chance of rain (& possible thunderstorms at night) ...Great At least it's via the mid-levels escalator, so fairly covered even outdoors on the way up!

The Cat

Veteran

I would save the cargo pants for more casual parties with friends. For this occasion, I would choose the simple yellow midaxi dress with a relaxed topper and relaxed footwear.

Stagiaire Fash

Veteran

The Cat, interesting. I see the pants as the most dressed-up option here.

Anonymous

I like the reddish orange dress!

approprio

(website)

Veteran

All these options will look great, but self confidence is the best accessory in these situations. If you want to impress your future boss, you need to wear whichever of these outfits makes you feel the most confident, and the most like yourself. Everything else will follow.

For what it’s worth, I love the satin cargo pants.

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