Robert's Rules: The First Date Outfit

After last week’s post about what to wear on a first date, we thought it’d be nice to get the male perspective.

Our friend Robert worked on Newbury Street in Boston, which (for the uninitiated) means he’s never afraid to tell us when our outfit looks bad.

Here’s what he had to say about what a girl should wear on her first date:

“A first date outfit must be thought about carefully, because this outfit is essentially a first impression to your date of who you are. Ideally, it would be a sexy (but not too sexy) outfit that incorporates your personal style. In general, no matter where you’re going, I don't think that you should overwhelm someone with an outfit that overtly displays your personal style--say, for instance, that you love mixing patterns: I would recommend working in a few pieces with maybe your favorite print rather than having an outfit made up entirely of different patterns. You don't want it to be too loud, just like you wouldn't want your outfit to be too sexy. I think a good first date outfit would also tastefully show off your body (leave your oversized pieces at home--for tonight, at least).

I think there are two types of first dates: upscale and casual. You should have a different outfit for each occasion.

If you’re going out on a fancy date,:

I think a form-fitting dress would be appropriate. I would stay pretty classic with the dress--let it show off your body--in a solid color, and then punch up the outfit in the accessories. Maybe a pair of metallic stilettos or a really cool bag that introduces a print, or maybe belt your dress (a belt can do a lot to define a midsection and create an hourglass shape--all good things, right?). And don't forget about jewelry! You can also say a lot with a chunky necklace or a cool bracelet. I would stay away from blazers for a first date look, just because I think it may look a little too corporate, and we want a first date look to be more flirty than business.

If you’re going out for a casual night,:

Every girl should have a flattering pair of dark jeans in her closet. Whether you look good in wide leg, boot cut, skinny, whatever--get a pair of dark denim, it may turn into one of the most highly used pieces in your closet. This would be the perfect time to break out the dark denim and pair it with a sexy top--one with a little sparkle to it or maybe ruffles (they seem to be in style right now), and finish it off with a pair of strappy sandals. Or, if you don’t feel like heels, do a nice pair of flats.

And since we’re heading into the winter months, let’s address outerwear. No matter how cold it gets, stay away from the puffy jacket. You don't want his first thoughts of you to be that he's going on a date with the Michelin woman. A pea coat will keep you plenty warm while also being stylish.”

He also has some words of wisdom for our male readers:

“Regardless of where you are going, take this as an opportunity to dress up a bit--but not too much. I wouldn't wear a sport coat, but maybe go for a nice button down shirt. And maybe layer it with a v-neck sweater. I think every guy looks good in a white button down shirt with a navy blue v-neck sweater layered over it. Navy blue is a strong, masculine color that looks good on any skin tone, and the white shirt will frame your face really well. What I’m saying is: guys, put thought into this--don't just put on a t-shirt and walk out the door.

And please pay attention to fit. There is nothing that I hate more than when a guy with a nice body hides it under an oversize sweater. I'm not saying wear something incredibly tight, but make sure that the shoulder seams end at your shoulders and that you can feel the fabric against your body instead of hanging off your frame. With sweaters, what you don't want it hanging off your body. You also don't want it coming too far past your waist (because then it'll be too long). Look for something that is trim in fit--you don't want a baggy arm either. If it’s too ill fitting, you'll look like you're wearing your older brother's sweater, which won't impress any girl.

Now for pants. This is when I also recommend dark jeans--they will work with almost any color (so you won't have to worry about matching) and they are incredibly versatile (they work in both casual and more upscale settings, depending on what you wear above the waist).

Again, pay attention to fit--every guy needs a pair of dark, straight leg denim. They shouldn't be so baggy that you cannot tell that there are legs beneath the fabric. Or also if you want, maybe a pair of cords or khakis, but I think dark jeans are a really stylish choice.

When you’re shopping for jeans, go for a straight leg jean fit--make sure the waist fits well (not too tight and not so loose that you need a belt to keep them from falling down) and also make sure that they sit on your waist (you don't want them to be too high up or else they'll look like the men's version of a "mom jean"). Look for mid rise fits. If you ever are in doubt, ask a sales person at the store! That's what they're there for. And just make sure the legs of the jean don't have so much fabric that you lose your legs in them. Gap's new slim fit 1969 jean is amazing and very affordable.

Now with shoes, go with a nice brown or black loafer, or, if you’re one of those guys that goes crazy about sneakers (I know a surprising about of guys who collect sneakers and pay attention to no other article of clothing), go with a dark, more dressy sneaker (I have a favorite pair of PF Flyers that I pair with almost everything). Don't wear a running shoe. Please.

And in terms of outerwear, go with a nice coat to finish it off, and if you have a scarf and it looks nice with your outfit, consider wearing that, too. (I think it implies that you give thought to your appearance, but if you don't want to, that's fine too--just giving you options!)”