If I wanted to date a woman from the cover of Good Housekeeping, I would hang out in suburbia. Fancy, but not too cocktaily…revealing, but still demure. Van Veen – How convenient that our date is a picnic and you brought the tablecloth! Buka – This is the girl you take cow-tipping or to a rodeo. It doesn’t look like you spent all day getting ready, but that you care about how you look and it’s sassy! 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.I’d wear different shoes — the red shoes are a little matchy matchy. Neffinger - It covers you up but flatters your figure. Good, clean fun until somebody gets pregnant in the back of the Ford pick-up. Santagati – It’s cute if you’re 50 and going on an “Upper East Side Luncheon” with your Yorkie. La Liberte – Actually kind of like this if you wore a cute little jacket on top, and KEPT IT ON.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.In 2015, one of three high school seniors reported ever having smoked a cigarette, according to the U. What they eat, wear, say, sell, and Snapchat is of great significance to their young fans.And though Jenner has claimed she doesn't "really" smoke, she continues to puff on a cigarettes in many of the videos and imagery used for her merch venture, The Kylie Jenner Shop.On a first date, though, this would make me wonder if I could afford to date you if I wanted to.
Buka – I call this one the “Julia Allison.” The ultimate in self-promotion.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? 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.She made fun of you in the high school cafeteria; now she runs PR for every celebrity you’ll never meet. 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.
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 La Liberte, 24, gay boy-about-town, stylist/publicist Unruly Heir Dr. 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! La Liberte - The jeans are way too wide and make you look bigger than you are, and the shirt is too tight in comparison.