Steve Jobs had it easy, he could wear a black turtle neck and blue jeans all day every day and it was hailed as genius. If that works for you, you can stop reading here. But if you feel that the “tech uniform” doesn’t allow you to be as authentic at work as you would like – this blog post is for you.

This is the outline of a talk I gave on December 2022 at the Google TLV office for a group of women in technical roles. I did not record it and I'm happy I didn't, because it enabled me and the participants to be much more open. I doubt I will ever give this talk again, it was a one time thing after being asked for it repeatedly - but I don't want it to become my thing. 
The first section covers why I think this subject is important to discuss, even if I would rather focus on strictly professional subjects. The second section has concrete tips on how to develop your own style and how to apply it.
As usual, this talk is rooted in my experience as a woman SWE, in Israeli/American tech, it might not apply to everyone. However, I believe it's an important subject that will be useful for many women in STEM and other male dominated fields, so here goes.

turtlenecks all the way down

Back to Steve Jobs. And Mark Zuckerberg. They famously wear (or, in Jobs’s case used to wear…) the same thing every day, allegedly to remove cognitive load. But there is something else at play here, Jobs and Zuckerberg and all the guys at the office, they can just wear the “tech uniform” – a hoodie, jeans and a T-shirt, it works for them because they are not being judged on how they look.

I just read an article about the power of dressing badly and how it can be used to appear to have other, more important, positive traits: “I don’t care how I look, so I do care about other things”, or “I’m a computer/business genius, dressing well is beneath me”. Unsurprisingly, all the subjects of the article were men.

double bind; 

We have a societal image of “what an engineer looks like” (remember the tech uniform?). There’s no class on how to dress (and maybe because some of us were geeky in high school? Maybe, maybe not), so we arrived at work and we’re not ready. Everyone’s wearing jeans and a T-shirt, maybe a polo shirt if someone’s being really fancy. And women do want to fit in.

But we’re also exposed to wider societal expectations on how women are supposed to dress and look. And we also want to be “good” feminists because clothes and makeup are superficial and we shouldn’t care about them. Right?

And… it affects how we’re perceived because maybe a junior engineer can “get away with” jeans and a T-shirt but as you become more senior suddenly… it doesn’t look right when you speak in front of an audience. You look… a bit unkempt? You don’t look like a leader. But a man dressed the same way would be just fine. But if you dress well then you can’t be really technical or serious.

It’s not easy to sort through all these contradicting expectations.

feminist break point

As an aside, in every social movement there are two approaches: One aims to “fix everything” and “bring on the revolution”, and the other aims to improve the well-being of individuals. Both of these approaches have merit, and honestly – we need both.

So, the revolutionary approach to women’s clothes are that no one should care at all how we look and what we wear in a professional setting, and I do wish we reach this utopia. It sounds great. However, in this world we live in – we are judged by the way we look. And if, for a second, we ignore the negative sides – it’s actually fun to look nice and have the freedom to express ourselves with clothes and makeup and shoes and jewelry and whatever makes us feel good. Honestly, men have a lot less freedom in this area.

I’d also like to remind you that men spend a lot of time, mental energy and money on lots of superficial rubbish all the time without a tiny bit of guilt. Cars and luxury watches and various status symbols that are supposed to impress other men (and they mistakenly think women). So I give everyone permission to spend their time, mental energy and money on whatever they want – clothes and makeup are looked down on because they’re girly and that’s the only reason!

In my mind, the feminist thing to do is reclaim the “girly stuff”. I can be an accomplished SWE and a leader and wear pink and dresses and makeup. And I use my status to normalize it for other women who should be free and comfortable looking however they want.

max(comfort)

When I decide what to wear I use the following guidelines:

I do not optimize on looking pretty. I mean, looking pretty is OK, I’m not against it. But it’s not the first thing I care about when choosing clothes.

I do not optimize on looking thin. Again, I’m not against it – I am part of the western world and I can’t deny that I am affected by the thin beauty standard. But this is my body, and I am not a thin person. I’ve had 3 kids and I’m in my 40s, I will never be 15 again and that’s really just fine by me.

I optimize for comfort.

There are two types of comfort: Physical and emotional. And I optimize for both, but actually – more on the emotional aspect.

Everyone has their own personal boundaries and comfort levels, the examples I give are my personal ones – it might be different for you and that’s perfectly OK.

So, on the bottom left we have uncomfortable emotionally and physically. This could be something like (for me) wearing a bikini in front of colleagues. This is the “absolutely not” zone. I will never do that to myself.

On the top left we have comfortable physically, but not emotionally. This could be something like wearing pyjamas to the office. They’re nice and soft, but you wouldn’t feel good emotionally wearing that all day in front of people you’re supposed to be working with (or, more accurately, I wouldn’t). This is the “yeah… no” zone – it might seem like a good idea at first, but the first side eye you get you’ll be wishing you wore something more appropriate.

On a slightly sensitive subject: I once won a session with a personal stylist and she recommended I wear V neck shirts. Apparently it would make my shoulders look narrower? Because women should take up less space in the world or something. But I digress. The point is that when I wore them I could see (not all but definitely some) men’s eyes do the “look down then back up” jump thing. You know what I’m talking about. I don’t think they did it on purpose and probably weren’t even aware. But I didn’t like it and it made me uncomfortable emotionally so I decided to not wear shirts like that anymore. A personal choice for personal comfort.

On the bottom right we have physically uncomfortable but emotionally comfortable. Like, high heels at a wedding. I’d do that on a special occasion if it really made me feel good about myself, but not every day. This is the “bearable, I guess?” zone. On the very far right of emotional comfort – I would sacrifice a bit of physical discomfort for feeling awesome. For me – that area includes pencil skirts which are definitely not the most comfortable item of clothing imaginable, but they are part of my style and I can’t part with them. The tradeoff is worth it (again, for me).

On the top right we have emotionally and physically comfortable. This is where we all want to be all the time – clothes that make our body and mind feel amazing. This is the good place.

min(effort)

Besides maximizing comfort, I aim to minimize effort – I don’t want it to be hard (and time consuming!) to buy clothes, nor do I want it to require daily effort to pick out clothes. I don’t enjoy standing in front of my closet for an hour trying to pick an outfit – what a waste of time and mental energy. I want it to be efficient – there are so many other worthwhile things I could be doing instead of scrolling on-line or, perish the thought, walking around a mall. And while I do enjoy shopping to a certain extent, I don’t enjoy the endless search and disappointment, or buying things that do not spark joy and stare at me sadly from the closet, nor the process of returning items.

dall-e

The last component of how I dress is how to create an image. Not an AI image (dall-e, get it?), a personal image.

When I did this live I told the participants to take 5 minutes to think of one word (two is allowed) that she’d like people to think of her when they see her. The only restriction is that the word cannot be something physical. Not pretty, not thin, not young… It has to be a personality trait.

Because young and pretty is not something we can control and it’s also very un-feminist so I can’t allow it. So much of the western fashion and beauty standard is about being small, thin, not taking up space – I want to push for the opposite – something that takes up all the space you want and deserve.

Take a couple of minutes to think about that before reading on.

Some of the words I heard were: Powerful, nice, professional, funny, a good sport… all legitimate.

I will share my own – my word is impressive. I’m more than happy to get other compliments but impressive is what I’m going for. This means that I sometimes choose impressive over pretty – for example, I look “prettier” with a nude lipstick, but I choose red or fuchsia or another dominant color instead because I want to look strong and powerful and impressive and that’s a different set of factors.

So this is my utility function:

max(comfort) + min(effort) + image

style guide

All of this was nice, but how do we put these abstract principles into practice?

SELECT clothes
FROM store
WHERE style = image

First we have to pick a style. Remember that word you thought of when you were thinking of the image you want to present? Think about some celebrity or TV character that fits that image. Go look for images of them online – what do they wear? What about their appearance speaks to you? What’s the common theme? Will it make you feel comfortable (emotionally and physically)? Collect these images, but don’t do anything yet. Give it time to settle in and revisit it later – you don’t have to start shopping immediately.

Once we’ve figured that out, we’ve already eliminated about 90% of clothes because they don’t fit the style we’ve chosen. This is the best possible outcome, as it reduces mental load – when I see a clothing item that doesn’t fit my style, I can just ignore it. I don’t try it on, I don’t add it to my virtual cart, I just move on. It saves so much time!

Do not throw away all your clothes. Start slow. Pick out one or two items you like and fits in with your desired style. Wear them for a while and verify it wasn’t just a fantasy and you actually feel good in them. You should give this a bit of time because any style change is hard at first.

If it works for you – go buy more. Doesn’t work for you? Give them away and don’t buy a similar item anytime soon! Maybe you need to revisit your style ideas and try a slightly different direction.

At the time I assumed almost everyone attending my talk was unhappy on some level with what she was wearing, but since reading a blog post requires far less effort - it's quite possible that most of the readers here are perfectly happy with what they wear and how they present themselves to the world and that is just fine. You don't owe anything to anyone, as long as you're satisfied.

<a>

Another way I reduce the mental load of selecting clothes (before purchase or from my closet) is to create an anchor (hence the <a> as the header of this section, get it?) and build outfits around it.

My anchors for work clothes are as follows:

• In summer: a pencil dress or pencil skirt and a shirt.
• In winter: skinny jeans, shirt, and a jacket. Sometimes maybe a cardigan instead.
• I always wear sneakers (even more so ever since I found that when I don’t wear sandals I’m not as cold at the office!)

If it’s not in one of those categories I do not buy it.

They’re not paying me so I won’t mention the brand of shirts I buy, but the important point is I buy a single cut in the same size in different prints. This means I have close to zero cognitive effort when I want to buy a new shirt. So much so that I have a custom search engine in my browser where I type in “shirt” and what I’m looking for and it goes to that site I use filtered by the cut of shirt I like.

So, inside that limited framework of clothes I have a decision tree for combinations that fit together. Say I feel like wearing my pink sneakers – this limits my other choice of clothing to a neutral bottom and top or a top with a print that includes a bit of pink (but not too much! I don’t like to be too matchy-matchy). The top I choose limits the jacket/cardigan options etc. Most of these combinations are preset in my mind and once I’ve chosen one item, the rest are automatically resolved.

This also helps me in my purchasing decisions: If I don’t know what I’m going to wear the new item with – I don’t buy it because I know it will just sit in my closet driving me crazy. Sometimes I will create a totally new anchor and cluster of clothes and shoes around it, in which case I will buy several items at once – usually shoes and clothes to match. I love sneakers.

change management

Now you’ve decided on your style and theoretically know how to build a wardrobe… don’t make the mistake of changing everything all at once. Sometimes you’ll see someone who decides to get rid of all her clothes and create a quality capsule collection that costs thousands of dollars because they saw it on some blog, or buy a ton of dresses and skirts just to discover they’re not useful or they don’t actually enjoy them. So take it slow.

If you’re used to wearing jeans and a T-shirt maybe going full on dressy-dress might not be the best move – the change might be too radical for you and honestly you might get some weird reactions from those around you. From my experience, whatever change you make in your appearance – people are going to be weird about it (even if they don’t say anything to your face). So not only will you be dealing with your own difficulty changing, you’ll have to deal with your surroundings. Every little eyebrow raise or well meaning yet out of place comment might make you regret you even tried.

bottom up

Start from shoes. They’re the least in your face (hahaha sorry not sorry). The further away from your face a thing is, the less obvious it is. It gives a little punch to your appearance without revolutionizing your entire look. And there aren’t many shoes that don’t look good with jeans. So if new shoes sound good to you – that’s an excellent place to start.

If you’re not a shoe enthusiast, a similar strategy is to start wearing skirts (if you were used to pants) or colorful pants (if you always wore jeans) or maybe something a bit more tailored (if you were very casual). Whatever fits in with your selected style. People don’t normally stare at your legs when they talk to you (or at least they shouldn’t…) which makes the bottom half of what you’re wearing less visible and easier to experiment with.

top down

Another option is to leave your clothes as they are and focus on changing your hair, makeup or jewelry. This will upgrade your appearance immediately without a huge investment. Add a scarf over a boring shirt, long earrings or a bold lipstick – it doesn’t have to be expensive stuff. Experiment and see what works! Be bold!

Let's talk about hair and makeup.

Shorts: The internet is chock full of information about hair and makeup which can be quite overwhelming at times. The problem with YouTube is the creators are incentives towards long videos which means that every tutorial includes dozens of products and take an eternity to watch and then do.  I don't know about you, but I have better things to do with my time. Short form videos like YouTube shorts and TikTok to the rescue! Even if they do everything at x2 speed, they don't have time to squeeze in a million products and it's still only 5-ish minutes of real time which seems more appropriate to me. 

Invest in foundation (time and/or money): You don't have to spend a lot of money on makeup in general, most drugstore mid-range products are just fine. The only exception is foundation/concealer: These are notoriously individual and they can make or break your makeup routine. Invest time (and money) in finding the right foundation for you. I use an $8 concealer as my makeup but if what worked for me was a $75 foundation I would use that (I tried them, they didn't). Ask for samples, try and try again, until you find something that works and stick with that (until they discontinue the product, which unfortunately happens from time to time).

Pick a guru, go from there: There are lots of influencers out there, pick one and let the algorithm help you find other ones. Remember that they make money for selling products so you should take their recommendations with a grain of salt, but they will often have excellent tips and tricks.

Practice makes perfect: At first the 2-3 minute hair and makeup routines will take you 10-15 minutes, but it's worth the effort, it will get better. My signature hair style looks sophisticated, but it's an adaptation of something I saw on TikTok and it now takes me less than 3 minutes to do (every single day, because mental load reduction!).

Timer.schedule(outfit);

And a few final tips about timing:

• A new job is hands down the best time to change your style. Wear the most extreme version of you on the very first day, as that will set the baseline. This is you and how you dress and it’s just the way you are. You might be apprehensive about making a big splash on your first day, but that day is a bit awkward anyway, use it to your advantage. If you wear some boring outfit some day in the future, no one will care, but if you don’t set the baseline it will be harder to change later (I say this from my own and other’s experience).
• Professional credibility: It’s all very nice for me to say “be bold”, I am a senior technical person with a ton of professional credibility, and sometimes it’s hard even for me. If you are more junior you may want to manage your image more carefully to build your professional credibility before going all-in with the pink and unicorns. It’s hard enough as-is building credibility as a woman, maybe wearing some boring clothes for a while is a price you’re willing to pay. If I’m being truly honest – you should definitely consider it and take it one step at a time.
• Job interviews: I try to take my style down one notch during job interviews. Maybe not bright red lipstick, something less prominent. Maybe not a red pencil skirt but a black one or red pants. I’m not going to dress up as someone else, but I also don’t want to introduce unnecessary bias.
• Managing stress: When I’m facing a stressful situation like an important presentation I will not wear something in the “also OK” zone, only “the good place” clothes. I do not want to add any physical discomfort when I’m already under stress.

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I think I will always be conflicted about this subject – should I even be addressing this issue as a professional woman in a technical role? Shouldn’t everyone just be able to wear what they want? But as I know from experience, appearance is not just a superficial concern and it will affect the perception of you in the workplace. Maybe it’s my duty to pass on how I manage my own image. I hope you found it helpful.