Fashionfilter: How can a female geek dress for success?
August 2, 2011 10:29 AM   Subscribe

I've been a programmer for my entire adult life, which means jeans, tshirts, and sneakers. I recently decided to move into management, so now I'd like to start transitioning into dressing better - for the management job I now have and for the next.

I'm a pretty average size: 5'4", size 8. I want to wear clothes that are the female version of the men.

Button down, tucked in shirts make me look like a lesbian. Skirts make me feel like I'm in drag.

What does that leave me?
posted by bikergirl to Clothing, Beauty, & Fashion (20 answers total) 8 users marked this as a favorite
I bought nicer tailored jeans, which I wear with tshirts and suit jackets. I do a lot of fancier tops with slacks or jeans and heels. It took me a full year to be able to pull out something that looked like me, but also like I was in charge. I also found that accessories (necklaces, belts, etc) helped a lot in having cohesive looks.
posted by Zophi at 10:39 AM on August 2, 2011

I used to feel the same way about skirts, and then I got a huge influx of skirts from a friend who moved suddenly and had to purge her wardrobe. Also, I'm poor and my old pants were nearly busted anyway. So I'm a skirt person now.

But I'm still super casual. Instead of a t-shirt and sneakers with jeans, I wear a t-shirt and sneakers with a skirt. The skirts are, for the most part, all A-line and around knee length, so I feel like I can sit/stand/walk comfortably without showing off the good china. They're all also all natural fibers, so I don't have any of the gross synthetic clingyness going on. (Caveat: I'm several inches taller than you; I've heard that if you're shorter, above-the-knee skirts are better, but I don't have much experience there.)

Try getting a skirt cut similar to this (not that pattern, necessarily, just that shape) and trying it out for a while. Just wear it like you would a pair of jeans. See how you like it.

This might not help you so much in the overall dressing nicer arena, but it will (might?) help you become more comfortable in skirts. Not that you have to wear skirts, of course, but I've decided that I like them a lot better than pants. Turns out pants (especially jeans!) are really constrictive and binding. I had no idea. I was the most anti-skirt person on the planet until about two years ago, and now they're pretty much all I wear.
posted by phunniemee at 10:46 AM on August 2, 2011 [1 favorite]

How do you feel about pantsuits? That's what a lot of women in management in male-dominated fields wear. (Also Hillary Clinton, of course--but you don't have to look like her.) Stores like Talbots carry both pantsuits and separates, and if you want to add a bit of color and style, Pendleton often has beautiful, artsy jackets.

You'd wear them with serious shoes (flats or low heels) and a bit of jewelry or a scarf.
posted by tully_monster at 11:16 AM on August 2, 2011

As an IT manager, I mostly wear dark-coloured slacks and (mostly lightweight) button-front shirts and blouses with one or more of: tailored to fit my shape (darts under the bust rock), strong colours, visually striking patterns (those stripes and paisleys and large prints the 20-year-old me would never have dreamed of wearing). Sometimes I'll wear an unbuttoned shirt or partly-buttoned blouse over a tank top or turtleneck, or a lightweight V neck sweater over a shirt.

I wear nicely tailored jeans about 1 day a week, either on a Friday or when I know I'm likely to be doing lifting and other physical work.
posted by thatdawnperson at 11:17 AM on August 2, 2011 [1 favorite]

I wore khakis, a cardigan sweater and a nice tank/camisole as my work uniform for years, and year-round: wool pants and sweaters in winter, light cotton khakis and cotton sweaters in summer.

The sweater is a nice, softer alternative to a suit jacket, but I can always pop a suit jacket on top of the tank and sweater (if I am wearing appropriate pants) if I need to. I also wear button-down shirts with sweaters, and leave the shirt untucked and the tails out on top of my pants. It's a casual look, but it's pulled together.

You can leave a button-down shirt untucked, but it should be fitted.

The sweaters and pants are neutrals; the shirts and tanks are patterned or brighter.
posted by hmo at 11:20 AM on August 2, 2011

Response by poster: These are some great ideas! Thank you all.

@tully_monster: I've never looked at Talbot's before...nice stuff. @hmo: I've just started wearing cardigans and I like them a lot, where do you like to get them?
posted by bikergirl at 11:32 AM on August 2, 2011

If you're wearing jeans, I'd wear dark jeans, and not so skinny jeans/not too tight. Stop wearing t-shirts, but collared shirts if you're wearing jeans or khakis. If you wear shirts that have shape to them, which most women's shirts do, you'll look less 'lesbian', as you call it. You can also wear boxy stuff and put on accessories to look more feminine, like undo a button, one, not 5. I'd also invest in several pairs of dark pants and tailor them to the height of your shoes. I tend to wear shoes that are 2-3 inches for work so I don't have to worry too much about the pants length to shoes. In regards to the top, I have the most trouble with this, because how a top looks on you depends on your shape (if you're petite with narrow shoulders, broad shoulders with big bust, small waist, or small bust with thick waist, etc) You're gonna have to go try on some shirts. You can invest in a few cardigans without having to wear a suit jacket. If your subordinates or colleagues are not wearing suits everyday, wearing them yourself may make you look stuffy...esp after having been wearing t shirts and jeans.

Also invest in a decent coat, depending on where you live. Even if it's not a thick winter coat, wearing a more shaped coat will make you look professional without being too stuffy. I love Ann Taylor for these types of clothes. I'd also go to the mall and checkout various tops. If you have a few hundred dollars to spare on wardrobe, I'd hire a personal shopper to work with you.
posted by icollectpurses at 11:37 AM on August 2, 2011

For me, I really like slacks and a sweater set. Here's one example (shell and sweater). It's almost as dressed up as a suit, but more comfortable and a more forgiving fit. You can also do a more casual version with a solid tank top and a sweater on top. I really like gap's perfect trouser (gap comes in lengths and has decent sales).
posted by mercredi at 11:39 AM on August 2, 2011

J. Crew Jackie fit me best, and they're always on the clearance rack.

But you can find cardigans like this anywhere: round neck, fitted through the body, three quarter length sleeves that ended right at the thinnest part of my arm, pearlized buttons that look almost jewelry-like, hits at hip and lays flat.

I also wear v-neck sweaters with a light-colored tank; the tank adds light under my chin so it looks like I only have one chin.

I hardly ever wear a crew-neck weater because I just feel it looks sweatshirt-like.
posted by hmo at 12:01 PM on August 2, 2011

As a tech writer, I frequently wore vests (as a jacket/cardigan alternative) with a sleeved shirt to dress up a little without going all the way to a suit. I would go for jackets and sweater sets in your shoes, but if you want to break yourself in easily without looking like you've had a manangerial lobotomy, vests are a halfway step.
posted by immlass at 12:56 PM on August 2, 2011

Apparently hmo and steal each other's clothes.

But what's underlying this is: once you find a new type of work uniform, it's almost as easy as jeans, t-shirt, and sneakers.

The one thing I would say is splurge a little on really comfortable dress shoes. That's a whole other question, but fund a couple of pairs you like. You'll never feel comfortable in dressier outfits if your feet hurt all the time.
posted by mercredi at 12:59 PM on August 2, 2011

You don't say how old you are, but I'm guessing you're around Gen-X' may not like Talbot's in person, their cut is a little "older." My mom really likes it and their clothes look cute on her (60's), but they look boxy/dumpy on me (20's).

I recommend checking out Ann Taylor Loft. They have great-fitting casual/business casual clothes.
posted by radioamy at 2:01 PM on August 2, 2011

If you want to look polished, slacks or trousers are better than khakis or jeans (unless it's casual Friday). The right pair of shoes helps a lot, as does the right length for the pants. Fit is a huge part of looking pulled-together. Nothing too tight; nothing baggy or sloppy.

When you get the pants hemmed (which you will probably need to do because of your height), make sure you are wearing the same shoes you plan to wear with the pants. Otherwise the pants will be too long or too short and the whole effect will be thrown off.

For tops, I don't think you need to wear collars or button down shirts. I would go with thin sweaters (short-sleeved or sleeveless, depending on the season) plus a cardigan that either matches or contrasts nicely. Something like this. It's a dressy version of a t-shirt.
posted by tuesdayschild at 2:15 PM on August 2, 2011

Response by poster: @radioamy thanks for the heads-up about Talbot's. Looking at Ann Taylor, they definitely look more modern. And yes, I'm in my 30s. :)

Sounds like most of you wear some version of a knit top or cardigan, I like the look and think it would be comfy and seasonless, especially here in San Francisco where it's almost always a little chilly.

Looking around, I think my best bets will be Ann Taylor Loft, J Crew, and Banana Republic.

I'd appreciate any others you can think of too.
posted by bikergirl at 2:48 PM on August 2, 2011

I've been wearing Talbots since I was in my early thirties--some of my favorite pieces come from that store. YMMV.

As you're probably well aware, though, in a field like IT or computer science, fashion sense is counterintuitive. You actually want to dress somewhat older than you are, and you want to look very no-nonsense and sensible (sounds like you've got that part down). In some areas of the country I've been in, however, everyone, including management, wears nothing but Patagonia because they take off after work to go hiking or mountain climbing--that look would probably work well in San Francisco.
posted by tully_monster at 3:04 PM on August 2, 2011

I've just started wearing cardigans and I like them a lot, where do you like to get them? - this may depend on your area, and takes some persistence, but I've been pleasantly surprised at the quality of sweaters I've turned up at the Goodwill. Given that wool can be spendy, and that wool sweaters are often just plain nicer to wear, it may be worth the effort.
posted by epersonae at 4:49 PM on August 2, 2011

This is pretty similar to where I'm at.
Here's what I do, but just my top 3.

1) Stalk Chadwick's and Land's End online. Yeah, crazy - but I'm a fan of three-quarter sleeve stretch button downs. Make sure you get princess seamed shirts.

2) Make sure I always have a pair of wide-leg trouser cut jeans in the darkest wash I can find.

3) A good wrap sweater for fall-winter-spring that works well to cover up in a cold office.
posted by msamye at 5:35 PM on August 2, 2011

There are some great clothing ('fashion') blogs out there. I emphatically suggest you find a few that inspire you.

The Sartorialist is great, for instance. Very varied. Skim a couple pages back, see if it's anything for you.

Danish style is currently very clean and elegant. A little too 'dry' by itself but what they have going on is a great base to build on. Here's one that seems representative:
posted by krilli at 1:43 AM on August 3, 2011

Hi you! You sound a lot like me! I was nothing but ripped jeans and ponytails and nerdy t-shirts for most of my career...and then halfway through last year, I started deciding to do the very same - dressing a little more professionally, or at least a little less like all of the scruffy engineers I work with.

Personally - and I'm citing this as more of an example and less as advice - I adopted the softer, more nerdy/bo-ho approach: I have a lot of dresses that I've collected, especially fitted one from etsy; shawls and cardis; and nerdy accessories. It's done a lot to distinguish me from being "one of the guys."

1. This may just be my start-up background, but this already puts me pretty far ahead of the pack. If anything, multiple female coworkers drag me out with them to go shopping because they want to switch towards a more personal/less casual look. And I'm 20x comfortable because I chose something that appealed to me, and wasn't the usual button-downs and pencil skirts or khaki pants (eww).

2. Hairstyles matter a ton. I got my hair styled and added some (drastic) color - even with the purple streaks, I still looked professional and slick, and it really made a difference in how people reacted to me. Your profile mentions you're in San Francisco? James Maher of Mahrz Salon in Redwood City is where I got started on having a hairstyle that was less pony-tail and more me without too much effort.

3. Dunno if you're also into make-up or not, but that, too, helped with my confidence and made me feel more put-together.

Feel free to memail me if you want to shoot the shit about what kinds of looks might appeal to you/figure out where to find the clothes to match? A side effect of my nerdy-fashion-soul-searching was a ton of reading about what I thought matched my personality and my lifestyle, and I've got a lot of references for other folks as well.
posted by amestar_runner at 7:56 PM on August 4, 2011

Response by poster: Thanks @amestar_runner - those are some great suggestions!
posted by bikergirl at 3:58 PM on August 9, 2011

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