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First Date Sartorialist: What Do Real Guys REALLY Think?

7 Guys (I actually know), 7 First Date Outfits (I actually own)

What did they REALLY think?  Check out my poll here!


Ricky Van Veen, 26, Editor-in-Chief, College Humor
John Mulaney, 25, comedian
Matt Titus, 40, dating coach “Matt’s Little Black Book”
Steve Santagati, 43, NYT bestselling author, “The Manual”
Kristian LaLiberte, 24, gay boy-about-town, stylist/publicist Unruly Heir
Dr. Bobby Buka, 33, celebrity dermatologist
John Neffinger, 35, public speaking coach, Huffington Post contributor


OUTFIT #1 - Casual

Juicy Couture jeans (Bleeker Street), James Perse tank top, Moe CLICK bag

Van Veen - I’m all for jeans, but there may be Amber alerts out for small children lost in those giant pant legs.
Mulaney - You look like a narc.
Titus - This is adorable. The casual is a lot less intimidating than high fashion and if you want a guy to ask you out, this outfit won’t scare them off!
Santagati – It’s simple, I know the girl wearing it is comfortable enough with herself to show up like this, and I get to see a hint of (sing like Julie Andrews here) a few of my favorite things – and I don’t mean silver white winters that melt into spring.   Mean bum and breast.  Just get rid of the turquoise table tennis paddle.
LaLiberte - The jeans are way too wide and make you look bigger than you are, and the shirt is too tight in comparison. You look like you are going to a hippie retreat to score some ass.
Buka - So close on this one! Imagine the jeans without bells and you’d have an easy winner. A clean, relaxed look – like the friendly, chocolate lab you always wanted.
Neffinger - Oh my God -- Jules, you're wearing jeans!  Did you actually put them on or just photoshop this?  If you showed up in this, forget the reservations, we're heading to the east village for people-watching, window-shopping, conversation and cheap eats.  Much as I love jeans, though, these are ridiculous, a designer version of the kind misanthropic teens scuff around sweeping the streets with. 

OUTFIT #2 - Straight from Work

Nanette Lepore suit (Bloomingdale's), Nine West shoes, Chanel bag

Van Veen - You didn’t have time to change after work? You’d think Scores would let you set your own hours.
Mulaney - This reminds me of that Michael Douglas movie DISCLOSURE where those people almost bone and then there is conflict.
Titus - Straight for work always makes a woman look smart (mentally and physically). I can never resist this look on a woman, it’s sexy for some reason, maybe the whole mental secretary with glasses thing? Where are the glasses?
Santagati – If you are coming “straight from work” to see me for a date then you better undo another button on your top or I’m going to want to talk about real estate prices, politics or accounting with you in this outfit.
LaLiberte - Kinda Princess Diana-ish before she got trendy. I’d wear this if you really don’t want any action, and you are trying to keep it professional. If you wore the jacket unbuttoned one with skinny jeans and stiletto boots that would be perfect.
Buka - I call this one the “Julia Allison.” The ultimate in self-promotion. She made fun of you in the high school cafeteria; now she runs PR for every celebrity you’ll never meet. 
Neffinger -  Straight from what kind of work?  The hem on the skirt is higher than all but the club dress.  Meanwhile, the black-and-grey check jacket with the giant buttons and rounded lapels says 'ladies who lunch.'  But somehow it all works together, a very cute outfit, say for an afternoon's shopping on Madison Avenue.  On a first date, though, this would make me wonder if I could afford to date you if I wanted to.

OUTFIT #3 - Little Red Dress

Diane Von Furstenberg dress, Nine West shoes, Moe CLICK bag

Van Veen - I like this – not too crazy, it’s playing it safe. Definitely good for a blind date with a bullfighter.
Mulaney - This is what I would wear if I was a dame. Then I would go to Filene's and kick some ass.
Titus - Little Red Dress is nice but screams out “notice me please.” I prefer the little black dress. This one reminds me of tomato sauce!
Santagati – This dress is the “Scarlet letter ‘B’” for BORING.  If I wanted to date a woman from the cover of Good Housekeeping, I would hang out in suburbia.
LaLiberte - I love this one.  Fancy, but not too cocktaily...revealing, but still demure. I’d wear different shoes -- the red shoes are a little matchy matchy.
Buka - Ok, ok, I get it - red dress, red shoes, red lipstick. It’s so put together I’m afraid to touch it. Can this girl even fart? 
Neffinger - It covers you up but flatters your figure.  It's eye-catching red with a big friendly bow.  What's not to like?

OUTFIT #4 - Preppy

Le Shack by Tracy Feith dress (Bergdorf's), Chanel bag, Bebe shoes

Van Veen - How convenient that our date is a picnic and you brought the tablecloth!
Mulaney - Duke Graduation.
Titus - No man can resist the preppy look. Just like Charlotte on Sex in the City! You look sooo innocent!?
Santagati – I went to school in Boston and the girls from Wellsley would wear this crap but were often good in bed.  When a girl wears this she’s saying “I’m conservative on the outside but naughty as all hell on the inside.”
LaLiberte - Preppy look suits you best, and it’s classy without being too frigid, because you show some skin. You look like you aren’t promising anything, but damn it would be hot if you did.
Buka - This is the girl you take cow-tipping or to a rodeo. Good, clean fun until somebody gets pregnant in the back of the Ford pick-up.
Neffinger - Julia, only you would ever wear this within city limits.  If the date in question is at the Kentucky Derby, then great.   If anyone else showed up in this dress in New York, she would have some 'splaining to do.  Like, for starters, why she stole your dress.

OUTFIT #5 - Little Black Dress

Chanel dress, Manolo Blanik shoes, Chanel purse

Van Veen - Ew. Very Charlotte. (yes, I watched SATC, and yes I abbreviate it SATC).
Mulaney - Meanwhile uptown, Charlotte and Trey blah bling blah etc. etc. etc.
Titus - This is my favorite. It is classy, sophisticated and not too done up. It doesn’t look like you spent all day getting ready, but that you care about how you look and it’s sassy!
Santagati – It’s cute if you’re 50 and going on an “Upper East Side Luncheon” with your Yorkie.  However, a little black dress is cute and always a safe bet, but it’s just that, safe.
LaLiberte - You look like you are trying to hard and your makeup is too heavy.
Buka - zzzzz…huh? Wha? Must have dozed off, because this girl’s BOR-RING! Looks like my Aunt Sadie! I bet she’s got the same nasally voice.
Neffinger - This is not the little black dress, this is a little black dress with some little doily details, something you wear to work because you need something conservative but not identical to what you wore yesterday.  Totally uninspiring, but totally forgivable. 

OUTFIT #6 - Sexy

Bebe dress, Moe CLICK bag

Van Veen - Wow, leave a little something to the imagination. For example, your cervix.
Mulaney - Are you holding a shoe-horn? What is that?
Titus - I’m a guy, so this is definitely my second choice. Leaves little, very little to the imagination and any guy who doesn’t put this one is his top two needs to be sent my way for relationship help!
Santagati – This is as hot as the jeans & tee but if a girl shows up in this she better be pretty confident because this doesn’t read “girlfriend material” it reads, “she’s gonna get it good.” HA HA.  It’s a great look if the girl wearing it knows how to handle the attention she’ll get, and I don’t mean be a bitch.
LaLiberte - Actually kind of like this if you wore a cute little jacket on top, and KEPT IT ON.
Buka - This is the girl Mom warned me about – this ensemble reads open Boxster and Bridgehampton. Order the salad, because you’re going to be buying lots o’ Veuve.
Neffinger - Well alright then -- straight to the club, do not pass go!  As long as you're not expecting me to take you to a fancy-pants restaurant, this could be fun.  If you want to be taken seriously as relationship material in this thing, though, you'd better talk about the more serious side of your life... which is tough to do over the sound system pounding out dance music.

OUTFIT #7 - "High Fashion"

Alice & Olivia coat dress, American Apparel leggings, Nine West shoes, Chanel bag

Van Veen - Where does she think I’m taking her, Mars 2112?
Mulaney - This is the worst thing I have ever seen and would only be worn by fools.
Titus - I am sure it works on the runway, but for some reason I am getting Star Trek flashbacks. No first date wear or second date wear either for that matter! But, love the Chanel bag!
Santagati – THE WORST PIECE OF SHIT I'VE EVER SEEN; astronaut meets aerobic instructor is never a good look. Plus the lipstick is like someone melted a red crayon and smeared it on your face.
LaLiberte - Leggings scare straight guys I think.  I think it’s a trend that is kind of out. The coat is cool but you look a little barberalla-ish.  Too extreme for first date.
Buka - This dress is melting my retinas! High fashion, my foot! Send this space girl back to the ship before that thing climbs up her face.
Neffinger -  Is this coat sealskin, or the stuff astronauts wear for spacewalks?  Demerits for being a crazy fashion victim, but since you are, you do get points for going all out.  If you wear something with this much character, though, you gotta back it up with fun conversation and zany stories, otherwise it makes zero sense.