Sexy clothes for a girl with a tomboy style?

April 4, 2008 1:08 PM

What should I wear to the bars with my new romantic interest tonight?

I'm going out to this bar: http://www.yelp.com/biz/el-rio-san-francisco tonight with a guy I've been on 2 dates with before. We're meeting up with a bunch of his friends (my first time meeting them!)
I'm a snowboarder, and my clothing style reflects that - a lot of Oakley/Volcom tshirts, down vests, jeaas, and fleece coats. I think I look good, but not sexy. None of my clothes show any cleavage or anything. I think he's the same style - he skateboards - but since I've only seen him twice, I can't say for sure. I don't want to look completely out of place with his friends.

What can I wear that will preserve my current, kind of punky style, but also be sexy? I'm thinking maybe a cargo skirt, or a v neck long sleeve shirt with a down vest. Please help!

posted by anonymous to clothing, beauty, & fashion (17 comments total)

Down vests are not for wearing on dates. It sounds like you would be comfortable in a nice pair of jeans or casual skirt with something like the v-neck top you described.
posted by ThePinkSuperhero at 1:22 PM on April 4, 2008 [2 favorites]

If you wore the outfit that you feel prettiest in, what would you be wearing? Could it be tweaked slightly (e.g. add a necklace, remove a down vest) to be date-fancy? I think you'll do better if you wear something that you feel good about already, rather than something that you think you "should" wear. If you've been out with this guy a few times before, he probably likes you for you, anyway.
posted by prefpara at 1:26 PM on April 4, 2008 [1 favorite]

Yeah, V-necks are almost universally flattering, but not too slutty. Leave the down vest at home. I'm a chemist, and I've never had the urge to wear my lab coat on a date. You want him to see that you're multi-faceted. Assuming that you are, in fact, multifaceted.
posted by Green Eyed Monster at 1:28 PM on April 4, 2008

Dark blue jeans and a black v-neck top are always a good sexy/casual date look.
posted by MsMolly at 1:28 PM on April 4, 2008 [2 favorites]

Some of the stuff over at Swell might be up your alley, for future dates.
posted by cior at 1:28 PM on April 4, 2008 [1 favorite]

Seconding the advice about wearing what makes you feel best--that's probably the best way to go. That aside, though... I know I can't speak for everyone, but cargo skirts are really not sexy. Do you have a really nice pair of jeans that show off your body? Those would be better. The top you describe is fine, but ditch the vest. If you want to show off your style, try using some accessories--do you have any cool jewelry or shoes or anything like that? Do you wear makeup? If you do, you can change that up to show off your style, even if your outfit is kind of non-descript. And your hair. I've worked at a lot of places where I had a blah, unalterable uniform that showed no style of mine whatsoever, but a lot of punk-ish people gravitated towards me because (I think) of accessories and makeup (I wore a lot of choker-type necklaces, rings, had a choppy, messy, punky haircut, wore bright eyeshadow and winged black eyeliner, etc.) But yeah, just do your thing. If you're meeting his friends, he likes you a lot.
posted by Polychrome at 1:30 PM on April 4, 2008

"Dark blue jeans and a black v-neck top are always a good sexy/casual date look."
posted by MsMolly.

MsMolly is a genius. Comfortable, cute, sexy, slimming. Still you, but dressier but still casual. Throw on cute earrings or a nice necklace (or both, but don't overdo it) and you're ready to roll. NO DOWN VESTS ALLOWED. Seriously.

Have fun!
posted by cachondeo45 at 1:37 PM on April 4, 2008 [1 favorite]

Ok cool - good to know. I really like my down vest, but I'll definitely leave it at home tonight! I think I'll wear a cute pair of jeans, a tight, gray, scoop neck Oakley long sleeved shirt, silver earrings and necklace, and silver kitten heels, plus black eyeliner for a sexy and punk look. Thanks!

(Oh, and the stuff at Swell is perfect - just the style I was looking for!)
posted by Maia at 1:41 PM on April 4, 2008 [1 favorite]

That seems like a great outfit to me. The jewelry and the heels make it dressy, but it sounds like it will still be totally your style.
posted by MsMolly at 1:47 PM on April 4, 2008

A good trick to retain your "style" while still dressing in a slightly different way is to make your accessories reflect your style. The right necklace, bag, hat or shoe can turn any outfit into "your look". It's how I retain a sense of who I am while having various pieces of my warddrobe exist for different aspects of my life.
posted by Stynxno at 2:06 PM on April 4, 2008 [1 favorite]

I think I'll wear a cute pair of jeans, a tight, gray, scoop neck Oakley long sleeved shirt, silver earrings and necklace, and silver kitten heels, plus black eyeliner for a sexy and punk look.

Your outfit sounds fantastic! I love it!
posted by prefpara at 2:13 PM on April 4, 2008 [2 favorites]

Your most flattering jeans and a slim-fitting v-neck with long or three-quarter sleeves. Casual, not too girly, but still sexy.
posted by Kololo at 2:17 PM on April 4, 2008

I'm straying away from the v-necks because those make me feel like I'm going to a job interview :)
posted by Maia at 2:19 PM on April 4, 2008

Strappy tank top, jeans, done
posted by whoaali at 3:36 PM on April 4, 2008 [1 favorite]

Keep in mind that half of el rio is outside. You do want to leave the vest at home, but you do want to bring something to keep warm if your big group ends up out back.
posted by Wolfie at 3:48 PM on April 4, 2008 [1 favorite]

i'm not a girly girl at all, and my default date outfit is always: dark jeans, black v-neck top, one piece of funky jewelry or a funky long thin scarf, interesting shoes.
posted by thinkingwoman at 4:45 PM on April 4, 2008 [1 favorite]

To paraphrase what a friend once told me:

"If it's gonna happen, a down vest won't matter."
posted by doncoyote at 5:50 PM on April 4, 2008