Help me dress powerfully and elegantly. I look quite young.
October 22, 2014 9:41 PM   Subscribe

I am in my mid-thirties, but people often think I'm about 22. I could probably pass for 17 in the right outfit. Young face. On top of that, I am slightly built and female. Not short, but delicate. People call me honey and baby and ask me where I go to college. I want to look like a badass who can win venture capital funding. I want to look as powerful and effective as I really am.

I am a bit out of the loop in term of what might be appropriate when pitching for venture capital in a field related to health and health technology. I am a bit out of loop on professional dressing in general. I recently recovered from a lengthy chronic illness and I am starting a new company now. I am putting a wardrobe together and I am trying to decipher some style rules.

I hear about "pops of color" everywhere when I read about what to wear to business meetings. I am afraid color makes me look younger and sillier. Also, the thought of tying a small, colorful scarf around my neck makes me cringe. It doesn't feel like "me". I am really drawn to black and grey with gold toned accessories, to feel and appear grounded and serious.

I am drawn to slightly androgynous looks like: http://static.zara.net/photos//2014/I/0/1/p/8181/222/706/2/w/1024/8181222706_1_1_1.jpg?timestamp=1413535178835

or:http://static.zara.net/photos//2014/I/0/1/p/7248/226/806/2/w/1024/7248226806_1_1_1.jpg?timestamp=1410777952366

I really prefer more modern style clothing, kind of architectural, like this http://minimalissimo.com/wordpress/wp-content/uploads/2011/03/zara1.jpg
and traditional outfits involving complete suits and scarves. I know that photo has a red shirt, but I like it in this case.

When I read about pitching to venture capitalists, some people say wear a complete suit. Other people say wear sophisticated separates. Some people say don't dress up too much or look too nice. Be the genius guy in the hoodie.

How conservative and formal do I need to appear? Any other tips for how I come across?

For reference I am thin, medium height, long limbs. Very feminine in the delicate sense, rather than in the curvy sense.

I am a creative, science-oriented person and will play the role of strategist in the new company.

I'm looking to dress in a way that acts as a foil to my apparent smallness and youthfullness.

Thanks!
posted by Pablito to Work & Money (48 answers total) 52 users marked this as a favorite
 
Get yourself some really great boots (even if no-one but you knows that's what's under your pants) - you'll walk taller and stand more confidently, particularly if they have a block or cuban (rather than stiletto) heel.
posted by Gwendoline Mary at 10:11 PM on October 22, 2014 [2 favorites]


There's nothing unprofessional about neutral colors and modern cuts. Your choices look very on-trend, professional, and fresh. What do your hair and makeup look like? A very good, contemporary cut (and maybe color) and well-applied make-up can polish things up significantly and that translates to not being seen as very young. Also, if you need glasses, wear glasses instead of contacts.

If you're pitching to tech, you'd be surprised by how into fashion many of them are. Start reading style blogs (you may like the sensibility of girls of a certain age) and sprinkle in some designer pieces.

Follow your own style and you'll feel more comfortable and that can help you to project confidence and maturity.
posted by quince at 10:23 PM on October 22, 2014 [6 favorites]


If I was built like you, I'd wear sleek modern suits and butchy hair. And honestly the hair probably makes up 75% of your age-appearance - if you've got the same flat-ironed armpit-length hair as everyone else, shake it up.

And yes to boots. Stick to sleeker rather than chunkier, because if you're petite they get clompy real fast, but a 1" heel slim boot under trousers and a tall riding boot under a tailored skirt.
posted by Lyn Never at 10:39 PM on October 22, 2014 [6 favorites]


IMO, the kind of presence you're looking for is as much about how you carry yourself and how you speak as it is about what you wear. There's a good TED talk on power poses and how they convey authority. There are ways of speaking that can help you seem more assertive to others.

So, in addition to switching up your fashion, you might want to take a look at some of these ideas and see how they can help you come across more effectively.
posted by zug at 10:46 PM on October 22, 2014 [23 favorites]


I don't know anything about the field you're talking about, but I will say that the examples you show look kind of young and casual to me. Experiment with dark lipstick. It can give a woman a much more intense look. Also, consider shoes with some real lift.

Again, I don't know the field. And I'm a drag queen, so my idea of fashion may well not be yours. But if you want to go for badass, I say think dark colors. Maybe throw some leather in there. Not like biker gear, but maybe a coat or a belt. If you're a natural pixie type, err on the side of going too dark.

But if you read as young, that's got a lot going for it. If you're good at what you do, people may take you for a whiz kid! In America it's usually much, much better to be seen as 22 than 30-something, sad to say.
posted by Ursula Hitler at 10:50 PM on October 22, 2014 [5 favorites]


I worked for a time at a venture capital firm as an office assistresant. [Typo, not going to fix] in SF in the late nineties. Below is only what I saw.

All the men dressed in the same epensive charcoal grey suits. I would dress in something recognizably expensive but not "Oprah" if that makes sense. If you can afford it. It's how they signal that you are in-group.

"Any other tips for how I come across?" They are all arrogant assholes. Seriously. This is a bit complicated and fucked but it's difficult to win at that game. The "dudes" will be stupid and insular in groups. Use the after meeting to develop relationships.

Your links return to this thread for me.

Best of luck.
posted by vapidave at 10:52 PM on October 22, 2014 [1 favorite]


The last outfit you linked is great- that shows amazing taste!
I think it's the accessories that are going to make it look "in-charge". Think bright red shoes and a little black bag with a bright red scarf tied around it. Change the red shirt out for white, and add a little gold necklace ( if you like). Think Stuart Weitzman for red heels or Anyi Liu for red flats. (I still get compliments on a pair of SW red heels I bought many many moons ago- they're one of the best investments I ever made!) And if you don't like red, try purple or green. Youre keeping your own essential style and comfort, but adding an extra level of oomph.
But really, it's about finding what will work for you, so that you aren't worrying about what you're wearing when you should be focusing on your pitch.
Also (and I may get shouted down for this) consider wearing a small plain ring. If uncomfortable wearing it on your left ring finger, wear it on your right. The unfortunate truth I have experienced is that this may up the amount of attention your audience pays to your pitch rather than *ahem* other aspects.
Kick some tail! :)
posted by susiswimmer at 11:52 PM on October 22, 2014


http://static.zara.net/photos//2014/I/0/1/p/7248/226/806/2/w/1024/7248226806_1_1_1.jpg?timestamp=1410777952366
i like this one. and maybe you could pick the right suit with it. it looks sophisticated and charming. good quality pointed high high heels is a must with this look plus a delicate sophisticated make up with pony tail>?
posted by Freyaaaa at 12:05 AM on October 23, 2014


I'm in the same boat, (mid 30s, pitching to VCs, look young as hell, stylistically confused) and I recently read Zero to One, which has a decent section on fashion. Interestingly, this book details how Peter Thiel's VC group instantly dismisses anyone dressed as a typical businessperson. They look for the "genius guy in the hoodie".

That being said, and I HATE TO SAY THIS, but you could probably use your delicate femininity coupled with a minimal, architectural style, to sell your idea... better than in a sloppy hoody. While women tend to get dressed up more than men (I think), what this book is advocating is an entrepreneur who is "outside of the box" both vision-wise and stylistically. You know what you've got to work with, and it seems like you are seeking affirmation that you are making correct stylistic decisions.

So, yes, I think you are on the correct fashion path. Good luck!

And PM me if you encounter any VCs looking to get involved with vertical agriculture, LED grow lights, or medical marijuana.
posted by special agent conrad uno at 12:10 AM on October 23, 2014


I won't comment on the styles because we are not at all the same shape, and probably not in the same culture (although you don't specify!). What I think we should have in common, though, is that whatever you wear will look much more "experienced professional" if you have relatively expensive makeup, hair, bag and shoes. And the bag/shoes/belt don't necessarily match per se but at least look like you meant them to go together.

Also: Make sure it all fits perfectly. Take it for alterations if necessary.
posted by emilyw at 1:13 AM on October 23, 2014 [8 favorites]


I think the outfits you've picked look good. I would avoid t-shirty tops like the one in the third image if you are trying to look older.

I really agree that hair, make up and bag make a really significant difference. Especially hair. I don't how you style it atm and to some extent I think the main thing, anyway, is that you make it look quite styled. Don't do a casual pony tail.

Pops of colour could make you look younger and sillier if not done well. You need to ensure that you stay with fairly muted tones and that the styles remain 'architectural' rather than frivolous. The looks you picked pitch that way so I think you are fine. I wouldn't avoid colour all together, in a best case scenario, because that can make you look quite generic, which in turn makes you look less confident, which in turn makes you look younger.

People who seriously ask you those things are being assholes. Anyone who looks above 17 should not be asked where they go to college, and nobody should be called honey or baby in the workplace. I would respond to those things with the appropriate level of death stare or just entirely ignore it if that is not an option. Those people will either be won over in time by getting to know you, or if they are not repeat clients, are just part of the world's sexist detritus.

Good luck.
posted by jojobobo at 1:34 AM on October 23, 2014 [1 favorite]


I suspect that what strikes the right balance of polished, professional, and (actual) age appropriate when it comes to work attire will depend *heavily* on local norms. My suggestion is not to buy a whole new wardrobe now just based on reading about what venture capitalists wear to their big meetings. Instead, buy a couple basic, non-offensive separates, and wait to see what women at your level and slightly above your level are wearing at your company or in meetings you attend the first few weeks of the job (hopefully there will be at least a few women in positions of power!). At that point you will have a much better sense of what will work, given your goals.

To me, the outfits you linked to, while cute, read on the youngish side. You might want to start with pants that aren't quite so tight and shirts that are a bit more streamlined. I understand those are the current trends, but trendy is going to be in tension with your goal of looking older, I think.

(For whatever it's worth: I think that looking older should probably not be your goal; as someone mentioned above, youth is over valued in our society--especially in women. You may want to use this to your advantage. Looking professional and competent will likely help you get ahead; looking older probably won't. I'm obviously not endorsing this, but it is what it is.)
posted by girl flaneur at 2:04 AM on October 23, 2014 [1 favorite]


I'm a woman business owner in a techie field, and like you I look younger than I am (even though I'm old!). I've been researching this a lot lately and experimenting, and so far here's what's on my short list:

- Boots with a sturdy heel. They make you taller and, more importantly, make you stand tall and feel more powerful.

- Cool hair color (not golden) with a simple, architectural cut

- Simple, dark clothing with an accent color, like you're already thinking of, and an interesting cut

- V-necks rather than rounded scoops or cowls (so I'd change the shirts in all the photos you linked to)

- Very little jewelry. To me, silver says "powerful" more than gold because it's a colder color.

- Assertive glasses (e.g. rectangular plastic frames in a dark color rather than rounded wireframes)

- LEATHER, the most expensive you can get. I have a black lambskin jacket that feels like butter, and whenever I wear that, I get respect, including guys leaping to open doors for me. The two most impressive women business owners I've ever met were both wearing a leather jacket, suit style, one black and one dark brown.

I think you're going in a good direction with the styles you linked to, but the super-skinny pants or leggings can easily look little-girlish, so you might want to consider straight-leg pants instead.

A skirt can be part of a powerful package, such as a non-flouncy grey skirt with black leggings, a soft black leather jacket, a v-neck shirt in one strong color, and black short boots. Maybe add a scarf for some pattern and variety. That's one of my standard "I rule!" outfits, and the skirt helps keep it from being too butch.

As others mentioned, body language and speaking style are super important. For example, looking flustered, digging around in an oversized bag for something, apologizing unnecessarily, moving abruptly, or talking when silence would be more effective all can make a person seem less impressive.
posted by ceiba at 3:44 AM on October 23, 2014 [15 favorites]


I no longer have this problem, so the standard advice to wait a few years does in fact work! You've got good advice to focus on hair, accessories, and body language and speaking style. I can't help directly with the pitching outfits, although I think you're on the right track with something tailored, largely neutral, but not a traditional suit.

Two more shopping ideas for you: Cos and Everlane. A woman at my office in her early 20s wears a lot of Everlane with sophisticated flats and heels and really succeeds in looking pulled together without looking stuffy. Some of the Cos stuff borders on quirky, which I think you want to avoid, but some of the other pieces look like they might work. Good luck with your new venture!
posted by chocotaco at 4:43 AM on October 23, 2014 [6 favorites]


I think it's lack of grooming that makes people think you're younger than you are. It reads as college kid. So a slick of lipstick goes a long way.

Seconding Cos - like a slightly quirkier Zara. Jaeger also do brilliant (tho pricey) versions of sleek interesting workwear.
posted by stevedawg at 4:52 AM on October 23, 2014 [1 favorite]


I too am small and young looking. Stay away from pattern. Solids are our friend. We can easily get lost in an outfit so nothing with a lot of detail and everything must be fitted. No scarves! Stay away from anything that adds bulk, including heavy jewelry. Heels are a must. Stick with smaller purses and stay as uncluttered as possible. It is always difficult for me to find clothes that fit great so I slowly build my wardrobe, relying on a few key pieces. Wear less make up than you think you should. Don't worry about the honey/darling/sweetie stuff. Those are the people who will help you out when you need it. Let them.
posted by myselfasme at 4:56 AM on October 23, 2014 [1 favorite]


I'd try Reiss and Theory. For ideas, at least, if they're out of your budget.
posted by Diablevert at 4:57 AM on October 23, 2014 [3 favorites]


I'm currently in the process of revamping my wardrobe for similar reasons (although I'm an ad creative, YMMV), and I've been really happy with my progress. It's really helped to think in terms of a 'wardrobe' rather than individual pieces, and I've used three resources to help myself.

(1) As lame as it sounds, I started putting together moodboards, following the guidance from this very helpful blog. This blog skews very 'fashion', but her advice on how to develop a personal style is very very helpful. I grabbed images of people who looked the way I wanted to look and figured out (a) the colours I was drawn to and (b) the shapes that I'm into (eg - it turns out I'm super into jeans hemmed J-Crewishly short - who knew?)

(2) Then I broke it down into a capsule wardrobe. I drew on Un-Fancy's numbers, though, TBH, I find that 37 pieces is a bit much. This really helped when it came to culling what I did have and identifying gaps.

(3) GET SHIT TAILORED. Seriously. Find a tailor you trust and use them lavishly. A bit of tailoring can make an otherwise meh piece look amazing.

(4) Learn how to iron a shirt. Learn how to polish and maintain your shoes. Learn how to replace buttons. Well-maintained clothes are essential for that 'pulled together' feeling.

How could this help you look more professional? Well, start by gathering images of what 'professional' looks like to you, then identifying the commonalities - the colours, shapes, and silhouettes. Then do a purge of your wardrobe and figure out what you need next.

I recently came across the blog Capitol Hill Style, which has some good finds for more conservative styles.
posted by nerdfish at 5:01 AM on October 23, 2014 [13 favorites]


Wear a suit. Go for a tailored look. No clothes that emphasize the shape of your body, like skinny pants, and no slouchy or flowing clothes either, especially not tops.

Check out corporette for lots of great examples of looks you could be wearing that will make you look more professional. In fact, Corporette just had a post about this: How to be taken seriously when you look young.

And I disagree with special agent conrad uno's advice to "think outside the box." This only works for men. You are already different for being a woman.
posted by chickenmagazine at 5:35 AM on October 23, 2014 [1 favorite]


There is no power uniform for women in Silicon Valley. That said, the photos you posted are awesome: those outfits convey intelligence, independence and success. They'll do fine.

Try Helmut Lang and Theory. City neutrals are fine: you don't need a pop of colour. You're right: definitely don't do scarves or froufrou stuff. Skip jewellery if you want. Wear boots. Be comfortable. But do, definitely, wear a jacket. Don't wear a skirt.

A good look would be: skinny jeans or dark trousers, a Theory T-shirt, ankle boots and a Helmut Lang jacket with a strong shoulder. Bag is harder but I'd go for a sleek laptop bag or sling, maybe in black neoprene. Keep your hair simple and sleek. Makeup if you like it, not if you don't. You'll do great. The pictures you posted are perfect.
posted by Susan PG at 5:50 AM on October 23, 2014 [4 favorites]


I'm not a women's fashion expert, but I do work in a start up and I think dressing in a suit will just make you look like a lawyer. A lot of the hotshit programmers and super-smart analyst types wear American Apparel (or a slightly more expensive version of same). Sweatshirts, jeans (or dress pants), cool sneakers or flats. I guess that's normcore? It's the female version of the dude in the hoodie. Execs sit up and take notice when they speak--partially because they are hella smart but also cuz of the [expensive, cultivated] look of "I'm too smart to wear an uncomfortable pair of shoes". Maybe not what you're going for as the CEO, but it does lend their presence an air of nerd-authority.
posted by Potomac Avenue at 5:59 AM on October 23, 2014


Also, don't use Corporette or Capital Hill Style as a guide -- they're great at what they are, but they're aimed at a totally different, east coast context. Too conservative and more accepting of femininity. Androgyny is your friend in Silicon Valley.
posted by Susan PG at 6:00 AM on October 23, 2014 [7 favorites]


Learn to do your makeup and get a very good haircut. Talbots, Brooks Brothers, etc. for clothing choices. Wear a watch. I recommend low heels to look older.
posted by discopolo at 6:03 AM on October 23, 2014


I'm probably a somewhat similar shape to you. I'm 24 and work in marketing (related to fashion) so in my work specifically there's more pressure to look cute and stylish more than sleek and business. However I think you'll need:

I nice fall/winter coat. Possibly a peacoat or trench. (If it's really cold where you are, I don't think a real deal winter coat is bad if you take it off when you arrive. It gets cold where I am - too cold for just a peacoat.)

A variety of blazers in neutrals with maybe one or two in a more pop of color like a maroon or something. That way you can wear a black or neutral top with a brighter blazer.

Also, as a small-on-top person, I find that blazers without lapels look WAY better on me. Otherwise I look like I'm drowning in fabric. The one you linked to in your third link is like that. (Also they have a few like that from Forever 21 that fit me great and look really nice!)

Some power skirts! (Actully, TBH these forever21 classic pencil skirts are pretty amazing. I was really surprised)

Make sure to get some tights or stockings. I personally don't think they're "required" to be professional, but I'm not in your industry. Get some in black, nude, and gray. They also make fleece lined tights that just look like tights and are good for winter.

Oxfords and/or heels. I personally don't wear heels a lot so I find Oxfords to be a nice professional/menswear inspired look.

Boots/Ankle boots. Always a must.

A variety of cuts of pants. I think skinnys, especially ankle cut skinnys can look a little young. I think every once in a while they're good, or if they're more of a slim skinny instead of a legging skinny they're more professional. I also like a good boot cut as it's not as wide as a flare.

Don't forget about some nice sweaters or cardigans. They can be great for layering on a more casual day.

Also blouses, I'd get some neutrals, some pops of color, some with a slight texture or pattern and then pair with simple jewelry. (I still have many statement necklaces which are "in" for my industry, though.)

Oh, and I shop at Nordstrom Rack, Forever 21, and Express most often. Forever 21's online fall selection is really nice (I HATE their summer stuff though.)
posted by Crystalinne at 6:51 AM on October 23, 2014 [2 favorites]


black+grey+gold makes me think you should try a search using the term "hard femme" if you haven't. A lot of the outfits will be casual, but you should get some good jewelry ideas and you'll see lots of women looking rad without "pops of color".
posted by momus_window at 7:05 AM on October 23, 2014 [1 favorite]


In terms of looking older (or rather, looking your age), check out this excellent post on the blog Extra Petite.
posted by insectosaurus at 8:25 AM on October 23, 2014 [1 favorite]


Unfortunately it doesn't seem like women are as accepted as 'the genius in the hoodie.' I think your ideas are spot on-- the modern/architectural looks are current without being weirdly trendy or overtly youthful. I'd second Helmut Lang and add A.P.C, Acne, 3.1 Phillip Lim, Jill Stuart, Rag & Bone. Also, the online store Totokaelo. If you can afford 'em, the Acne pistol boots are pretty much killer. Rachel Comey makes some really nice boots, too. For cheaper versions of this stuff, I've had some luck with Madewell, even J.Crew, hell I've found some pretty damn nice blazers at H&M. Also, ebay is your friend.

In terms of color, don't worry about having to add pops of hot pink. If your clothes are interestingly cut/draped, that already gives them visual interest and in a much subtler way. Stick to what makes you feel grounded/powerful. Oh yeah, and get things tailored. Everything. I'm a similar size to you and things tend to hang off me awkwardly.
posted by sonmi at 8:53 AM on October 23, 2014 [6 favorites]


I'm a college professor and I easily get mistaken for a student if I don't watch my presentation. I recently chopped off my mid-chest-length hair to a pixie cut and have been told I look older. I also always wear either a necklace, typically either real silver or gold (aka not cheap mall costume jewelry), or a scarf. I don't wear full suits to work, but I do dress in at least business casual and for more important events typically wear a dress with a structured jacket. Makeup and particularly lipstick also has been helpful.
posted by vegartanipla at 8:55 AM on October 23, 2014


I also think you're on the right track. I like the third look the best because of the highly structured blazer. I also like the advice above re: leather, if that's something you're drawn to. The palette you're drawn to will work well. I especially like a gold necklace against a heather gray. Or maybe you're a watch person? A man-sized gold watch would look fantastic, none of those dainty lady watches. "The guy in the hoodie" doesn't apply to women, imo. That's just another instance of male privilege. Wear what makes you feel powerful and pro.

Make up and a good haircut will also be important. I think a strong lip (look for matte or semi-matte finishes) lends age and seriousness to appearance. The TED talk on power poses above is worth watching too.
posted by purple_bird at 9:12 AM on October 23, 2014


If you have the time, I'd go to the library and flip through issues of Fast Company. (The website doesn't seem that conducive to browsing.) They feature a lot of STEM women of all ages and at all stages of their career, and while they may be posing for a magazine article many convey the look you are going for.
posted by Room 641-A at 9:16 AM on October 23, 2014 [1 favorite]


I can't help with the fashion advice, but one thing to think about is that venture capitalists are less interested in personal appearance and more interested in the entrepreneur's ability to execute. This is not to say that looking like a slob will get you venture capital investors, but it is also to say that you need not worry about looking as polished as, say, Marissa Mayer, in order to get investment.
posted by dfriedman at 9:20 AM on October 23, 2014


Also I've gotten good blazers from H&M, Zara and Nordstrom's Halogen brand, if that's more your budget.
posted by purple_bird at 9:22 AM on October 23, 2014 [1 favorite]


Oh hi, I'm a petite babyfaced female science strategist person who has sometimes rubbed shoulders with the VC community. Are you my clone? Nthing blazers, blazers, blazers. I actually get most of mine from thrifting, and it's all about the fit, not the brand. If you run cold, they're extra good, because no one wants to be up there shivering in a room temperature controlled for a bunch of dudes in suits and have people thinking you look super nervous when you're really just freezing.

Beyond that, the advice here is good, but I think the specific audience matters, and whether or not you're CEO matters, unfortunately. (I feel like the presentation requirements for female CEOs are a lot higher than for other senior level positions, especially if you're out being The Face of The Company to raise funding.) When I was doing more of this kind of thing I actually got away with shrugging off a lot of conventions, but I think some of that was being in Silicon Valley and working with founders in tennis shoes, and some of that was that I made a conscious decision to have my image and attitude communicate "I'm not here for my looks, gentlemen" which meant zero makeup, boyish shoes, and nice tailored jeans and a sports jacket if I felt like it.

I'd be happy to help vet outfits privately if you want to PM me.
posted by deludingmyself at 9:35 AM on October 23, 2014 [2 favorites]


I hate to say it, but some of the advice you are getting here is really, really wrong. Let me try to unpack a little.

Silicon Valley values youth, arrogance, men, money, technology, individuality and risk-taking. When it comes to clothes, what's highest-status is to not care about clothes at all, and to not have to -- that's why Mark Zuckerberg famously wears a hoodie and shower sandals. Back in the early days of PayPal, Max Levchin bought himself a crate of cheap t-shirts so that when he was in the middle of a coding binge he could easily swap out a stinky shirt for a new one. That tells you everything you need to know.

It's like that because engineers are the scarcest and most valuable resource in SV, and the messy brilliant obsessive hacker is the stereotype everyone is aiming for. High-status tech company engineers wear sloppy clothes because they want to (or because the stereotype says they should want to), and the fact that they're *allowed to* distinguishes them from lower-status engineers at places like banks and insurance companies. It also distinguishes them from their colleagues in e.g. biz dev or marketing, who are lower-status and whose jobs require them to dress more conventionally.

I'm not advising you to wear jeans and a t-shirt to your pitch meeting: you shouldn't. It'd be a risky play for anyone, because basically it's saying "I am so awesome I am gonna ignore convention and you will give me money anyway" or maybe even "I am so awesome (geeky, hyper-focused, tech-obsessed) I don't even know the convention exists." But it'd be a very poor risk for you, because as a woman you can't fit into the hacker stereotype, which means you'd just be read as young and in over your head. Better for you, and for most people, to bow a little to convention and dress reasonably well.

But. You need to stay as far away as possible from the east coast working woman uniform, because it is basically the opposite of the messy hacker. Fussing with scarves and brooches, being deliberate about colour coordination, caring about the size of your pearls like they do on Corporette -- all that sends precisely the wrong message. (As does anything overtly feminine, like skirts or pumps or prints.) In west coast tech, the Corporette-type outfits would read as conservative, over-cautious, old-fashioned, stuffy, and approval-seeking. You would be interpreted as a person who cares too much about what other people think, who thinks about clothes instead of thinking about work, and who focuses on self-presentation because she can't hack it on substance. (I hope it's obvious that I am just describing this, and in no way endorse any of it. It's massively misogynist, etc.)

So. The look you want is "I don't care too much about clothes. I'm not trying to hide anything or over-manage how you perceive me. I'm focused on the work. That said, I know how to dress and when the time comes you can stick me on TV and I'll do fine." Which to me results in a look very much like the photos you posted. Just dress like yourself, and add one strong dark jacket for added authority and in deference to the occasion. You'll be great :)
posted by Susan PG at 9:39 AM on October 23, 2014 [13 favorites]


There's no indication that OP is in Silicon Valley or not in Silicon Valley.

OP, a note about your location would really help people answer your question.
posted by Kwine at 10:12 AM on October 23, 2014


I'm in the same boat as you, like a delicate bird who looks twelve.

I don't dress high powered because I work in the trades, but if you're just going for older, I haven't had one person ask me which high school I go to since I made some changes to my wardrobe.

-stockings (I like sheer black or grey instead of tan, personally)
-heels. nice ones. made of leather. that cost more than $35 and don't have an exposed platform or open toes. I like pointy toe.
-pencil skirts
-silk blouses
-blazers
-no more dangly earrings or big hoops, I wear diamond studs, or other studs (even if they're big and clunky looking.)
-pencil in your eyebrows.
-paint your nails.

and I think the #1 all important factor: throw out all your lipglosses and get some lipstick and lipliner. I have thin crappy lips and this still looks nice and makes me look way older. Rimmel has a line by Kate Moss right now and the number 08 is gorgeous and makes a nice starter lipstick. it's amazing how much older wearing lipstick makes you read.

Yeah, I dress a bit like a funky secretary right now, but "people now think I'm over 25!" which is brand new to me and feels great!
posted by euphoria066 at 10:15 AM on October 23, 2014


Response by poster: The thread seems have veered in the direction of Silicon Valley, so I wanted to nudge it back to a different direction. At this point, I don't know to whom or where I will be pitching. My science is actually biological science and I would partner with some computer science people to get the job done. So, I am not a hacker and my concept is not primarily software related, rather related to health with technology employed in an innovative way.

I've got the minimalist pixie cut. I'm picking up a blazer pattern in the suggestions from you guys.

Would appreciate if you would check out the following shoes, clothes, accessories:
This oxford shoe, but in black:
This ankle boot:
Shoes in red?:
I have these. They don't look skintight on me like they do on the model:
I've got this top in dark grey. Looks graceful on me. Drapes well:

Leather jacket:
posted by Pablito at 10:20 AM on October 23, 2014


I've been researching blood tests recently and came across Elizabeth Holmes, who invented a method for running dozens of test on one drop of blood. She is about your age and dresses in a Steve Jobs inspired black "uniform". She looks kick-ass. Note her body language, here, here, here and here.
posted by travelwithcats at 10:40 AM on October 23, 2014 [6 favorites]


It sounds like your style is basically good, but here's where you should focus your attention to detail, and more importantly, this is where you need to spend some serious money:

- shoes. right now high quality leather shoes in strong accent colors (red, maroon, dark green, purple, make sure they're dark, saturated jewel tones not pastels) are the feminine equivalent to men's "power ties". Stick with conservative styles, rounder toes and moderate heels, not spikes or stilettoes.

- bags. there was recently a fantastic bag thread on AskMe and I'm on a mobile which precludes searching; hopefully someone links it here. your bag says a ton about you. get the best, most professional leather portfolio type handbag / laptop bag / briefcase you can afford. several hundred dollars is not too much to spend on this as it's a social signifier.

- collared shirts and blouses. wearing well fitted / tailored blouses with pointed collars a la menswear inspired (not peter pan or rounded or v-neck or cowly / slouchy collars) is one of the subtle ways to achieve a less "girly" and more "serious businesswoman" look. c.f. newscasters and female politicians.

- tailoring. find yourself a decent tailor and get everything, and I do mean everything, impeccably fitted. this means you'll need to avoid things that are too trendy or fast-fashion.

and yes, a nice ring that mimics a wedding band without being one, along with a pair of glasses can help. when I was a very young-looking twentysomething attempting to focus on building a resume without being constantly harrassed or condescended to, I always wore an inexpensive but classy looking silver celtic knot band (I still have it, it's on my right hand now that I'm legit married) and a pair of tortoiseshell frame glasses with clear (no prescription) lenses. yeah, it sucks to have to be disingenuous like that, but I was also way tired of being hassled and ignored.
posted by lonefrontranger at 10:58 AM on October 23, 2014 [1 favorite]


As for feedback on your recent links, I like all of them except for the ankle boot, which seems a bit dowdy to me. Ankle boots remain very popular this season, so there are lots of options that look much more fresh than that one.
posted by quince at 11:28 AM on October 23, 2014 [1 favorite]


One really important way that style guides can lead you astray is that they are fundamentally about helping women look good to other women and to men who know what to look for. That's probably not your audience. Your audience mostly doesn't know what's on trend, doesn't care about and won't look at your shoes, and won't care about bags except at the broadest possible semiotic level ("backpack = young," "briefcase = old").

What signals "not young" to me is: happy-medium makeup and hair (visibly and distinctly "done," but nevertheless subtle), traditionally styled, well- but not aggressively-fitted dark solid suit over a solid white or ivory blouse, a modest complement of jewelry (one stud in each ear, a simple slim rope necklace fairly close around the neck, a ladies dress watch without any bling, no rings other than wedding + engagement). (Engagement ring alone screams "young.")
posted by MattD at 12:38 PM on October 23, 2014


Hair and makeup cannot be emphasized enough. Whether you go more traditionally East Coast polished or a little more laid back Silicon Valley-style, perfectly-groomed hair, nails, and makeup (in the appropriate style) are key to unlock that magical transformation into badass business woman. This has all already been mentioned, but I want to point out that none of it's really worth it without regular maintenance. So budget and plan not just for clothes, accessories, and the initial makeup inventory, but also for biweekly (or weekly, depending on your body) mani-pedis, haircuts however often your stylist recommends to keep your preferred style perfect, and regular dry-cleaning to keep your clothes looking their best. And learn to keep your shoes, belts, jewelry, and other accessories in fantastic shape.
posted by rhiannonstone at 1:04 PM on October 23, 2014


Re: your follow-up: I like the ankle boots. I am pro red shoes and that silouette, but not suede. I'd vote for a sumptuous looking leather if you can find it. The leather jacket is spot-on. The grey trousers are great, especially with something with a heel.

I disagree with the "rounded toes" advice re: footwear above. Sure, no stilettos but there's something deliciously threatening and female about a good pointy toed shoe. You want your heels to be as walkable as possible though. Something you can stride confidently and quickly in.
posted by purple_bird at 1:50 PM on October 23, 2014


Back here to respond to your follow-up:

The leather jacket is similar to mine, which has a good effect on people. I think the collar strap and shoulder details on the one you linked to make it more casual and less classy than it could be, but it looks good. Another style to consider is less motorcycle-y and more suit jacket-y, though those are harder to find.

The ankle boots might be more powerful if the heel were separate (not a wedge).

I'm not a pump wearer but if I were, I'd agree that suede wouldn't be high on my list because it can look battered and scuffed so easily. Red is hot, though.
posted by ceiba at 3:30 PM on October 23, 2014


You're trying to convince people that the "corporation of you" is a good investment. What you wear might make a difference to a point, but really, it's all about competence and the confidence that comes with the knowledge that you can succeed at any goal you put your mind to. Good ideas are a dime a dozen. People who are capable of turning a good idea into reality are much more special.



1) No flat shoes. Those first two shoes you linked in the comments are a 'no' if you're already coming across as small and youthful. The third ones are good. The right person can wear them in pink suede. Flat black leather in that same style would be my style preference. Here's something I'd consider wearing, plus those pumps you linked, a nice watch, small diamond/pearl/gold studs, and maybe a camel blazer. The key here is to figure out what makes you feel comfortable and secure, and then make it slightly more professional.

2) You aren't coming across as less powerful only because your face looks young. It's all in your body language. Women have to pay special attention to the cards they're dealt with their physical appearance. Your goal here seems as though it's to stop coming across as childlike. Have you tried going to a flea market and bargaining for an item? Try to go really, really, really low...to the point of embarrassment. Do this like 10 times at different booths. The key here is to get yourself used to failure when pitching something. This will help much more than anything else. Also, go rock climbing, sky diving, whatever. Push your own boundaries. Believe in your own competence in other areas, and that will shine through in other interactions. You have to be able to walk into a room and not feel nervous to talk to anybody.

3) You're pitching your project and trying to get funding. Great. What relationships are you looking to build? I think a lot of failure in business is people who are inexperienced and treat the experience as a transaction rather than a relationship. It's not just about their money. Don't try to make it about their money. It's about them and you and building something together. It's about culture. It's about fit. Because, well, if they fund you and you're successful, they're going to be dealing with you for a very, very long time. Money is relatively easy to come by, but successful working relationships with people you enjoy are much more special.

4) You say you're trying to work with software people. Okay, here's my suggestion: learn a programming language and complete a project. (This will help with my suggestions in part 2 as well) If you want respect from any good software engineer, the fastest way is to be competent. The easiest way to let a software engineer know that they might be able to walk all over you is this mentality: "So, I am not a hacker..." How are you going to hire the right people for the job when you feel unable to even try what they're doing? You might get lucky, which would be great. :)
posted by semaphore at 3:54 PM on October 23, 2014 [1 favorite]


I think you might like Mango. I feel like a lot of it says "smart, capable but creative professional" and the look is adult -- it's one step above Zara/etc. in my mind and it helps to get ideas in terms of styling. I like something like <>this outfit for you (you can, of course, probably find similar pieces elsewhere).

It's a joke that as women get older, they cut off all their hair. I am not recommending a mom cut at all, but a good cut with some style will make you look older. When I cut off my waist-length hair a few years ago, I ended up looking both a bit older but also more hip. A good haircut can make an outfit.
posted by darksong at 5:07 PM on October 23, 2014


I think your taste in clothing is fine. I wonder if something else is leading to being called "honey" and "baby" (setting aside the issue of how obnoxious that infantilizing behavior is...sigh). What stood out to me from your first three pictures was the body language of the woman in the third image; she looks less powerful because her toes are turned in. In short, you may be able to get more traction by working on stance. Your clothes seem fine.
posted by MrBobinski at 6:49 PM on October 23, 2014


Three thoughts:

1. Can you channel Tilda Swinton?

2. You linked to a bunch of stuff at Nordstroms. They have free personal stylists. You tell them what you're interested in, they bring you options. My friends who have done this have loved the whole experience. http://shop.nordstrom.com/c/personal-stylists

3. Alternatively, subscribe to a service like Stitch Fix (https://www.stitchfix.com)? You select a style profile, and give them your sizes, then they send you clothes regularly. You keep what you want and pay for them, and send back the rest.
posted by semacd at 11:11 AM on October 24, 2014


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