One of the many benefits of being a columnist/celebrity interviewer is you can push off those cash spending casualties as work related expenses. Underage Halsted Street hookers, booze, and of course impromptu trips to New York to interview music industry execs and party with porn stars. It seemed like a perfect idea, a week of shopping, partying, oh and work. I would soon find out though that NYC is no place like home and if I was going to blend in as a young New Yorker I had to look the part.

Us Midwestern boys would rather a t-shirt, jeans, and a baseball cap over a stuffy designer suit any day, but when in Rome, I suppose. Here I was, in the city that never sleeps, prepping for a night of debauchery. While wickedly drunk is wickedly drunk no matter where you are don’t think for a moment I’d take the chance to be shined out by a local in my tame Chicago duds.

Everything here is newer, edgier , the go-go boys are more naked and sluttier, and the music that’s hot right now won’t hit your city for months. It seemed like an appropriate excuse to put a dent in the vacation budget. No mission of high importance is without an appropriate team of course. I enlisted the help of dance/pop recording artist Gioia to tote me around town and be my eyes and ears of what’s hot in chilly New York. You’ll remember Gioia from the wildly successful girl group Expose, back in the late 80’s when I was a homo in the making and pop divas were becoming gay icons. The still hot, still ridiculously in shape crooner is currently shaking up the dance charts with contributions to Queer as Folks soundtracks and her bouncy solo artist releases.

The songstress picked me up promptly in the traffic friendly Times Square. Ignoring angry New York drivers she excitedly popped out of her sleek, black Mercedes and gave me a big ol’ bear hug. Hoping she wouldn’t notice I held on for a second longer, examining her vintage leather trench with fur lining, sexy! We then headed to the famous gay hood Chelsea to find the appropriate digs for the New York queer bait on the scene. After good hard trial and error we stumbled on to a fashion goldmine, appropriately titled "Bang, Bang." Why appropriately titled? Well from my observations you certainly get more "bang for your buck" or "if you wear these clothes, you’re going to get seriously banged," those are crucial deciding factors when shopping right? The manager floated all around us, grabbing sizes, commenting on our asses, and throwing different outrageous outfits on us exclaiming "I know my gay men, you love it, right?".

Hmm so this is where fag-hags go to die. Regardless, I walked out with some steals: A down jacket with fur trim (54.99), a motor oil inspired button up polo (59.99), "gold digger" tee(19.99), X-ray jeans(120.00). Cha-ching, left with enough in my New York budget to head to a trendy Chelsea munch spot.

We then strolled into the very lovely Food/Bar. A simple drink/eat up, conversation place with great atmosphere and waiters that could easily pass for pool boys. Miss Gioia and I munched on some fried calamari, washed it down with a little white wine and got down to business. Being a New Yorker all her life and spending most of it in the image conscious entertainment biz I wanted to get her take on NYC style. Here’s what the quirky singer had to say:

Justin) How has your look/style evolved from the days in Expose’?

(Gioia) I don’t think it’s actually evolved. Jesus, I’m exactly the same, I didn’t realize it till now. Ok maybe the hair has a little less lift but that’s just because I can’t find the aqua net in the pink can.

(J) What do you think a New Yorker’s philosophy on style is?

(G) Anything black, big sunglasses, high heels and cell phone surgically attached to head!

(J) What is your one favorite piece of your wardrobe that you’ve worn to death and can’t live without?

(G) The black leather bra! It was my good luck bra for a while I couldn’t do a show with out it.

(J) Do you have any past trends you totally want to bring back?

(G) Opaque leggings under shorts. Seriously, I’ve always been a fan of the bolero jacket. Is that still in?

(J) Describe the sexiest outfit a man could wear.

(G) I like a guy in a nice tailored suit, birthday or otherwise. Oh, and skip the tie.

(J) What something a guy will wear that’ll turn you off?

(G) Something that looks better on him than on me!
Bitch!

(J) Do you let your gay friends dress you up?

(G) All the time, that’s my favorite part! I went to the White Party in Miami dressed as a bride without the actual dress, just the petticoats and the fun stuff underneath, I think I danced with every person there. No proposals though. Maybe next time I’ll wear a tux!

(J) Finish this sentence “_____ “is better than shopping.

(G) Sex! Of course did you really have to ask me that question?
And think of the calories you burn off, those new clothes will look just FAB!

After the eats and equally delicious convo, Gioia and I made one more pit stop on our feel good, spend dough date. Not caring if we’d fit into the clothes we just bought, we headed to an upscale bakery and stocked up on chocolate croissants cookies, and whatever else was sure to bloat me and in turn kill my chances for a NYC lay.

Totally exhausted, I made my way home, drowning in bags. I looked in my wallet and suddenly that shopping high wore off. My 20’s and 50’s had become stripper style dollar bills and I realized I could only afford to shop like a New Yorker for one day. Well, good thing I stocked up.

Gioia’s currently in London writing new music and promoting the release of her single, "Why Did You Call Me Again?". Look for the release of her remake of "Your Love Is Lifting Me Higher," in the US this summer. Check out gioiabruno.com for more info.

(View column photos by Frank Failing, Male Image Photography who also made the trip to NYC)

Justin Boltz takes us through the glamorous world of hot stars and gay influentials with a unique voice that always proves to be provocative. As a contributor for Gay Chicago Magazine, BOI magazine, and ChicagoPride.com, nothing's ever off limits with this youngster columnist.