Author Kendall Farr has a charming and succinct way of putting across her thoughts about fashion and style. I particularly liked the second chapter of Style Evolution, “Dressing Your Body Now”, where she writes that “Good fit is the equivalent of six months in the gym”.  It’s a clever way of pinpointing the true advantage of superbly fitting clothes. 

I spend a good deal of time helping clients and forum members achieve good fit because it makes a huge visual difference. It sharpens your style by making it more polished, professional, chic and sophisticated. Although you may not aspire to looking sharp in this way, good fit does above all, flatter your body and enhance the silhouette of your ensemble. 

That being said, when you browse popular fashion websites and check out the outfits of stylishly savvy fashion bloggers, you’ll also find them wearing ill-fitting garments — and pulling off the look. I’m not talking about the intentionally oversized cut of a boyfriend blazer and shirt, a poncho or a soft boxy blouse. Or slouchy trousers that are roomy at the waist because the point is that you belt them to create a pouffy effect around the hip area.

I’m talking about lasses who wear items like tweed jackets and button down shirts that are clearly two or three sizes too big, but get away with it (see this photo of Garance Doré on The Sartorialist, for example). They scrunch the sleeves, perhaps add a belt to define the waist, wear it over a pair of short shorts and finish off the look with a killer pair of peds and headgear. The fact that Garance is drowning in her ill-fitting jacket while the rest of her outfit components fit pretty well is, quite ironically, stylishly acceptable. In fact many people would aspire to replicate this cool look. The ill-fitting statement has a creative, unique and “rough around the edges” integrity that is appealing. 

The fit contradiction is food for thought. On the one hand, I am a strong advocate for good fit because it has extraordinary figure flattering advantages and it sharpens your style. I will absolutely have my own clothes altered to achieve a perfect fit. Effective tailoring is an extremely important part of my style because it helps me to achieve the crisp, strong look that I’m after.

On the other hand, I see how a garment that is ill-fitting and not (conventionally) flattering can be made to look interesting and distinctive by a style savvy dresser. 

The question is, when do ill-fitting garments look creatively cool and when do they look unstylish? Or does good fit trump the “cool factor” no matter what?