First Date… What to Wear?!

While talking to my dear friend about what to wear on a first date (which is a nice way of saying we were trying to figure out how just much boob and/or leg she should show), I came up with the idea of having a basic T: A ratio. That is, how much cleavage (T) and leg (A) a gal can sport at once. I think the T is directly inverse to the A. Which, again, is a nice way of saying if you’re giving it all away up top, cover up the gams a bit. Conversely, if you are wearing 2-inch inseam shorts (and go on with your bad self if you are), wear a long sleeve or loose fitting top. Some women do this so effortlessly (a la my dream girl Kate Moss), while others (Heidi Montag of my most hated duo on the planet “Speidi”. If that name doesn’t ring a bell, you are officially my idol) are running around town with barley contained nipples and almost visible underwear.
So I thought I would break down some of my favorite first date looks using my carefully crafted T:A ratio rule….. enjoy

Shorts with a loose fitting blouse:
I love the look of nicely tailored shorts (I say keep the inseam from 3-5 inches) which really highlight a great pair of legs and a blousy top. This is a great look year round, well at least here in Southern California. In the summer or spring, pair white or dark denim (darker denim is a bit dressier for evening) shorts with a floral long sleeve, semi sheer blouse. For the impending fall and winter, I love wool shorts with a tie front blouse and opaque black tights with black heels or ankle booties (the black tights and black shoes will create a long and lean line, or legs that go on for days as I like to call the look). Top it all off with a fitted, almost shrunken blazer and you are good to go.

Loads of cleavage with pants:
Now, I am one of cleavage’s biggest fans (and dare I say when in Europe, a fan of a slightly visible nipple as well), but there’s a classy way to advertise the goods. In the summer or spring, I love a deep plunging neck silk camisole (but, take note gals, the insanely deep necklines are good only for gals with a B or smaller cup, think Kate Hudson. Anything bigger looks vulgar) with either higwaisted jeans or dark skinny jeans. This fall and winter I love the look of silk V-neck camisoles in deep plums and smoky grays with dark skinny jeans and a bright, stacked high heel (probably in yellow or red). Wear a fitted cashmere cardigan to complete the look.

Now, ladies, I can’t help your dates with their looks, but here’s a basic rule of thumb I tell my single friends; if he is wearing Mandals (male leather sandals), carrying a Murse (man purse) or wearing capri pants, calmly pick up your gorgeous oversized clutch and… run like hell.

Ladies, please dress your age!




Since I was just featured in InStyle’s Fall Makeover Issue as a specialist on how to dress when you’re fifty, I thought I like to share my pearls of wisdom for dressing at every age. It seems like this should be a no-brainer for us gals, but we’ve ALL seen them; the 20 year-old hiding behind a college sweatshirt and Levis from junior high, or (god bless her) that 50 year-old mom rocking the too tight bedazzled jeans, the bedazzled tee, the bedazzled trucker hat, the bedazzled… well, you get it. As a wardrobe stylist, I have seen it all throughout the years and have honed a few tips for women of every generation. Enjoy:

20’s
Guess, what? You’re not in college anymore, so please, please burn those flannel PJ pants and University sweatshirt. Conversely, you’re not a teenager anymore ( ahhh, the good ol’ days), so please keep your midriff and bum crack covered at all times. Your twenties are a perfect time to explore every style (classic, Goth, modern, feminine etc); and you lucky bitches still have the bod to pull off most looks. Experiment with color, fabric and style to find a look that is truly your own. I recommend playing with a few trends but mixing in some classic staples as well. For example, this fall, the boho look is making a strong comeback. Wear a boho print mini dress with black tights and peep-toe ankle booties, and top it off with a fitted cardigan. It’s a perfect balance of trendy meets classy.

30’s
By now, every woman should have her own signature style and know what she can and cannot wear. Perhaps you have learned that not everyone is meant to stuff themselves into skin tight jeans like a little sausage about to burst out of its casing. Highlight your best assets in a classy way. Love your gams? Wear a structured mini skirt with a blouse and leather jacket. Have fab cleavage? Show it off in a top with a plunging neckline, and wear fabulous high waisted jeans (Try Rich & Skinny’s, they’re amazing, you’ll instantly look 5 pounds slimmer). It’s all about proportion and rocking those assets you feel most comfortable with.

40’s
40 is the new 30 in my book. You just keep getting better with age, as should your style. Wear tailored pieces such as pencil skirts in lace (one of fall’s favorite fabrics) and a crisp white blouse. Mixing patterns in a subtle way is one of my favorite trends for ladies in their 40’s. Keep the 2 (or 3 for the hard core fashionistas) patterns in the same color family to keep the look more chic than clown-ish. Accessory wise, I think a lot of ladies date themselves by wearing just studs and a dainty necklace. You have many, many good years left my dears, so please stop accessorizing like your grandma. A chunky men’s watch looks gorgeous on a lady’s delicate wrist. Layer a few delicate necklaces, or bracelets; wear one giant and fab cocktail ring. Have fun with it!

50’s
No mid-life crisis here ladies; please don’t raid your daughter’s closet in attempt to look younger; you’re not fooling anyone. There is good news is though, you don’t have to dress like a nun. One mistake I see a lot of women making is hiding themselves under baggy layers to look smaller. This technique actaully has the opposite effect; it makes a body look bigger and dumpier. Keep your lines clean and fuss free. Try a wrap dress. it’s one of the most universally flattering looks a woman can wear. It nips you in at all the right places. Pencil skirts are a great look as well. Just pay attention to the hemline; keep it in one inch above or below the knee. Anything shorter looks a bit street-walker and anything longer visually cuts your leg in an unflattering place.

Okay ladies, I think I have given you some gems to work with here. Now, go try some of these looks and watch your style evolve.