Well I’m a geek and do consider myself pretty stylish. I strongly suspect her friend feels comfortable in her style and isn’t sure on how to incorporate geek style into average daily life and is likely not a great shopper in general so has her favorite outfits that she wears all the time. As much as I love steampunk most of it isn’t appropriate to wear to the average office. So I disagree with Mallory on how to deal with her friend who doesn’t dress appropriately for various situations. I recommend a couple of options.
Casual fashion intervention
The first one is take her shopping with you and while at the store pick out some items she can add to her wardrobe that would look nice. ‘Oh this would look SOO cute on you try it on’. Now if she’s resistant to shopping or going to the mall than that might be an issue as to why she has a few outfits that she’s likely gotten at a convention or from a geek site.
Cosplay at work
The second is that I love your style but that it’s not work appropriate so it’s standing between you and success aka more money to be able to fund her geek lifestyle. Going to cons and buying stuff is expensive so money is appealing. If she wants to wear her cosplay at work she’ll have to change it up a bit and do more of the steampunk suits (menswear style) or if she’s in a business casual office a jacket over the t-shirts or simple skirt or pants and just use what management wears as a jumping off point to style more in her comfort zone.
I suspect your friend needs a big push not a nudge to start to incorporate her geek style into a wardrobe that will fit in a variety of situations from work, to dating, to formal events and just socializing with friends. Since you can wear a Star Wars style dress to a wedding (as long as it’s not Princess Leia’s white gown) that would look great. I love the dress but it was a simple draped grecian gown. I’ve always found that a lot of people look at fashion and clothes as modern armor that protects them and she’s found what she likes and just needs some help with figuring out how to incorporate her style.
Not everyone is a born shopper or enjoys going to the mall and if you do please give your friend a hand with navigating ‘grown up’ fashion.
My roommate is a beautiful soul. Her wardrobe, not so much. She wears cheap, often tacky dresses (most of them with a “geeky” theme like Star Wars, Dr. Who, etc) all the time. Many of them are full-length ball gowns with petticoats underneath. Her employers appreciate her hard work and dedication, but I’ve noticed they never take her very seriously and she’s never been put in charge of the department she was trained to take over. I adore her geekiness and think style is personal and subjective, but I know not everyone else sees it that way. Her last boyfriend ended things after she wore an R2-D2 gown to his sister’s black-tie wedding, even after he begged to buy her a new dress. She rarely gets a second date. I have tried getting her to try on other clothes, but she seems uninterested. I think it’s entirely possible the outfits are a shield for her insecurity. I believe there is someone out there who will love her the way she is, but part of me wonders whether it’s time to sit her down and be honest because it’s holding her back professionally and romantically and she doesn’t seem to understand why. I’m worried I’ll lose my friend. Should I butt out or speak up?
—Say No to the Dresses
I know my answer should be something about how your roommate has the right to be her geekiest and most authentic self at all times, but I agree that floor-length Dr. Who–themed gowns are not always the appropriate choice for weddings or the workplace. That said, I’m not sure you’re best situated to talk to her about her fashion sense. You say her last boyfriend ended things because of what she wore to a wedding, so presumably she’s aware that her sartorial choices are off-putting to some—I don’t know what you could say to her that’s more effective than “You wore an R2-D2–themed dress, so we’re breaking up.” When it comes to work, your theory that her clothes are keeping her from being named director of her department is just that: a theory. You’ve already tried encouraging her to try other outfits and she’s refused to take the bait. It’s up to her employers to say something if they want her to dress differently at work, and it’s up to your roommate to find romantic partners who like her style. Despite your claim to love her sci-fi bent, I suspect you don’t like (and are perhaps embarrassed by) your roommate’s clothes and are looking for a justifiable excuse to call an intervention. You don’t have one.