Why does the character Molly Kagan, played by Debra Messing in the Starter Wife, look so uncomfortable in the clothes she wears on the show? The fashion seems so forced. It’s not that the clothing is over the top, it seems unnatural. Debra Messing is such a natural, gifted actress and she is certainly reason enough to watch the show. She’s referred to as the next Lucille Ball for good reason, because she’s funny and we can easily relate to her. The stylist/costume designer is just not getting it right for her. I think there’s a push from the producers or whoever to have fashion play a big part in the show, and it comes across as fake. The girls from Sex and The City, and even Lipstick Jungle do a much better job pulling off high fashion. Carrie Bradshaw’s style was usually way over the top, she looked comfortable in the clothing, and we completely bought it. Why is that? Is it because those two shows are NY based, and therefore the fashions look more at home walking the city? Do the fashions that Debra Messing wears in The Starter Wife not fit the city she’s in? I’m interested to hear your thoughts on this one, because I love the show I just find that aspect of it so distracting.

Purple is everywhere this fall, and the best thing about the trend is its versatility. It spans so many categories —scarves, bags, dresses, and shoes to name a few— and unlike some other trends, this is one that anyone can pull off because the options are endless. Making purple work really depends on what you pair with it.

One important part of the purple trend is picking the right hue. We’re not talking neons or pastels. This trend calls for a deep, saturated purple which the women above display. The key to making these outfits work is the combination of purple with neutrals: blacks, browns, and metallics become the perfect backdrop for such a strong shade.

The problem with the outfit on the left is the multiple shades of purple. We’ve got blue-purple shoes, a light purple bag, and a dark purple shirt, resulting in purple overload! In the middle, the woman has paired a purple top with other bright colors which battle with the purple, and end up looking unfocused rather than sophisticated. Lastly, we have a purple shirt and a matching print skirt, which takes away from the excitement of the purple trend and also looks dated. Make sure your purple is a surprising pop in your outfit, not just an expected match.

Plaid can be bold, rough and grungy, but we’ve found real life women who have dared to wear the look with grace.

New York women have decided: they love the plaid mini dress. And it’s the perfect item to take you from Summer to Fall. The women above pair these cute, breezy dresses with light heels and sandals, but these plaid pieces can easily be transitioned into Fall. On the left, the woman daringly pairs her yellow and black plaid with punchy colors to play up the summery nature of yellow, but this can easily be matched with darker colors for fall to create a completely different look. The woman on the right wears a dress with a flirty back cutout that can be warmed up with a shrug for fall. This simple dress shape proves to be an easy way to wear a daring print.

Of course, plaid can easily go awry. On the left is a classic example of ill-fitting plaid. These lines in the print are no longer straight; they are following every single curve of the woman’s body, which isn’t flattering. While plaid should be tailored, it should never be skintight! The woman in the middle pairs plaid shorts with a print top, which makes the outfit way too busy. Though a careful mixing of prints can sometimes be genius, this looks messy and unplanned. While this last outfit on the right may be stylish in the moment, lets be realistic: I don’t care how trendy maxi dresses or plaid are, in a few months this woman will be sure to look in her closet and wonder why she ever wore that much baggy plaid at once.

Below this announcement, you’ll see the 1st installment in a new series we’re introducing at the style observer. It’s called: style observed and it will come to you on style observer weekly. In this new series we’ll take a cue from the magnificent Sartorialist and his incomparable street-style mode of fashion commentary. In our take, we’ll show you how it a trend or look was done right…..and not so right - and how to work it into your own personal style. We’re not out to embarrass anyone, only educate. You’ll never see faces, only examples.

This 1st installment is a look at this years hottest trend (we claim it as such because it is by far the most searched term this year for us). Of course, we’re talking gladiator sandals. Style Observer contributing editor Ellie Jabbour combed the streets of New York for these great examples. Ellie twitters at @elliejabbour.

We hope you like the series and we’d like your feedback. We have several more in the works but tell us what topics you’d like captured. Enjoy!

The Summer is coming to a close, and we’ve made some observations about one of the summer’s biggest trends. As we’ve discussed before, the gladiator sandal is a daunting trend for anyone to just to throw on. Here’s our solution: we’ve scoured the streets of New York and found women who have pulled off the look, as well as some fashion blunders.

These women display two key elements for pulling off the gladiator sandal. The first is keeping the look feminine. Pairing these sandals with scarves and skirts is an easy way to avoid looking too tough. A second tip: regardless of the length and width of your legs, these sandals can add some bulk. Combat this with a high waistline or a short hemline, which will elongate the leg and balance out your look.

Beware of pairing gladiators with dresses that cut the leg at the calf! This isn’t going to flatter anyone. Instead, opt for a maxi dress or one that hits above the knee. Also, watch out for any white or gold clothing that will leave you looking ready for battle. While the gladiator sandal is a strong look, the women above have pulled them off in their real lives, free of stylists and runways, so give in to the temptation and try it yourself!