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How to help a friend who doesn’t dress appropriately at work

Don’t come at me with pitchforks because THERE IS an unspoken dress code at most workplaces.

Obviously if you work in a creative one, you have more latitude but for me, these are hard stop rules for anyone, man or woman:

  • No plunging or revealing necklines
  • No too short shorts or skirts (that fingertip rule where if you put your fingers down and the fingertips of where you graze is how short you can go, is a ridiculous rule. Just wear bottoms at most, a few inches above the knee ONLY and you’ll be fine.)
  • No flipflops

That’s about it but within those 3 simple hard stop rules, you have SO MANY MORE subtle rules in each industry, workplace, etc.

Generally speaking, I also find:

  • Childish patterns – Not so much hearts, but things like cartoon racoons, or anything that would look cute on a child but a little offbeat on an adult
  • Too loud patterns or colours that clash terribly – this is very avant garde; save it for the weekend or nights out if that’s your style. I’m not saying to suppress your love of bright neon yellow, but understand that at the office you’re not on a runway, you’re there to work and it can be distracting
  • Inappropriate sayings/patterns – I once saw a fabric with dildos hidden all over it in a fashion challenge on TV, which would definitely count as inappropriate for the workplace
  • Extremely tight and/or sheer or see-through clothing – You’re not at a club, please don’t wear leggings as pants, nor should you ever wear an embellished sequined or pearl bra underneath a sheer white shirt (yes, I have seen this and it was a LOOK).
  • Too detailed or embellished – sequins, ruffles, peplums, pleats – they are all great in moderate or very small doses, not in large chunks
  • Any clothing that is distressed and looks it – Ripped jeans (ironic or not), slash-cut t-shirts, peekaboo holes all over your body, etc… all not a great idea generally speaking, but things like lasercut patterns that look like lace on a skirt hem can be pretty
  • Any jewellery that is jangly, or overly strong perfume – In fact, I prefer no perfume at all, just deodorant. People can be very sensitive to smells like I am, and if I am wrinkling my nose near to you I do not mean to, but I cannot breathe when you have bathed in cologne. Similarly, jangling necklaces, earrings, bracelets.. these are all extremely distracting and annoying

Even within those mini rules, you can also go very, horribly wrong with things like unflattering cuts, etc.

I’m assuming you already know how to dress for yourself and are doing fine, but let’s say you see a friend or colleague who is brilliant in every way, smart, kind, etc, but none of it shows in the clothing she/he is wearing. How do you bring it up?

Obviously it comes from a place of caring and love – you want them to succeed and be promoted because they’re great, but their packaging (let’s face it) isn’t very appealing.

Much like when we go to a store and see items for sale, we always gravitate towards the ones that look the nicest to us. Usually the packaging is spot on, and we can get suckered into buying it because it LOOKS good, never mind how it actually performs.

(At least, this is still me, and I have to wrench myself back from buying prettily packaged items and stick to stuff I know that works and is worth the cost.)

People, react to other people in exactly the same way.

If you see a person nattily dressed in boots with holes, a dumpy sweater, random pants and zero care with their appearance, versus someone who does the same job (presumably), dressed in a more presentable way with a button-up shirt, nice pants, simple but nice shoes — who do you think gives off the better impression of being more competent?

If you take care of your appearance, it shows, and people naturally take that and translate it into how awesome they think you are at your job; if you care THIS MUCH about what you wear, your work must be equally as great.

Of course, if you care too much about what you wear and it really looks like overkill, then it becomes a negative against you, but let’s not get into that for now.

Try suggesting you two go shopping together

If you know them well enough, suggest a shopping trip. Steer them towards items and have them try things on outside of what they are used to, and when they do, exclaim over what it looks like on them (AMAZING!), and why (oh look at how it nips in here and gives you this long clean line…).

Suggest colours that are flattering for them, or tell them: PLEASE try this on! I want to see how you look in it.

Subtly compliment other well-dressed colleagues

Feel them out. Say things like: Oh he’s dressed really well today, those shoes and that shirt really make the whole outfit. What do you think?

What they say, will reveal a lot – maybe they don’t feel safe or comfortable enough to learn how to dress like that, so they don’t and stick to what they wear because it is their comfort zone. In that case, jump in and gently suggest that you’d be happy to help them.

Maybe, they look at the outfit and see someone ‘beaten down’ and ‘conforming to an ideal that is not their style’, and then you will know how to approach it with something along the lines of — Oh really? I don’t think so. I think they just look well-dressed, put together, and you know, it really helps with managers when they see this because she looks the part that she’ll likely get the promotion for.

You could also bring up that dressing well, doesn’t mean you are conforming and agreeing to become a sheep, but more that it gives an air of professionalism that your work otherwise doesn’t visually shout out. You don’t have to give up your personality in what you wear, you just need to redirect it or tone it down a little.

With that, you can figure out what they think without directly asking them, and see how you can steer the ship towards you offering to help them with a mini makeover.

Hire outside help

This one is sneaky, but you could always say you’re hiring an image consultant and say — Oh I’m doing this thing with an image consultant to see how I can present myself more professionally and better at work – would you like to do it with me? .. and make it a team thing, where you’re then encouraging.

Who knows, you might even pick up some new tips for yourself which is a win-win.

That way, you aren’t telling them, an outside professional is.

Obviously, the most direct way is just to tell them

No matter what you say, it will hurt. No matter how nicely you say it, it will hurt. Or how they take it.

Loving truth, no matter how gently given, hurts.

I’d rather (personally) try the 3 methods above before just telling them directly that they don’t dress appropriately for the office for the job that they want, EVEN THOUGH THAT IS WHAT IT IS.

Thoughts? Suggestions?

I’ve never had to do this in reality, but this would be my approach.

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