Tips From the Top: Fashion Goals For an Almost 30-Year-Old

Bill Cunningham, The Times' legendary fashion photographer, built a career on capturing others' personal style in candid street snaps. Like many influential industry figures, Bill's own style has always been unobtrusive, defined by one distinctly unglamorous item: LL Bean duck boots. Those duck boots have pounded the pavements of New York for decades — and, what started as a nod toward practicality, has become synonymous with the man himself.

With Bill's duck boots in mind, I've vowed that all future purchases must stock my own armory of fabulous, functional pieces. These must be clothes to see me through both the seasons of time and the fickle seasons of fashion; if an apocalypse happened tomorrow, I'd expect to look good during it.

It goes without saying that footwear is fundamental. Ballet pumps by French Sole or Repetto are an enduring lesson in chic, while classic white tennis kicks are equally timeless. A sturdy collection of jeans — skinny, wide-leg, and a few vintage Levis 501s thrown in for good measure — add variety, while a well-fitted jacket polishes any outfit.

My own collection of clothes, a jarring cacophony of prints, patterns, and styles, requires the stern hand of Balenciaga to sort the wheat from the chaff. There are pieces that should have been discarded years ago; some sort of color-coding system would also help instill order.

But I suspect Cristóbal was referring to more than just a well-ordered wardrobe when he uttered these words. Many outfits are most striking in their simplicity — and a capsule wardrobe, heavy on the neutrals and classic with its cuts, promises lasting elegance. So where do I begin? Amping up my collection of white shirts seems like the best place to start, as does buying a collection of tailored black pants. Fabrics should also be taken into consideration: high-quality cotton, linens, silks, and cashmere have proved fail-safe investments in the past.

Iris Apfel, a fashion force not far off 100, defies all conventional wisdom about style. With feathers, loud prints, lashings of jewelry, and a penchant for oversize glasses, her clothes celebrate fashion as something fun.

A streamlined working wardrobe needn't mean weekend clothes that follow suit. Rather, I'd like to use my off-duty time to channel an Iris-inspired jubilance when it comes to fashion. That means sequins, costume jewels, head-to-toe prints, feather boas, and anything else that takes my fancy. A bejeweled turban? Iris says yes. The only thing worse than making a fashion faux pas is being too scared to try in the first place.

Confidence can't be bought, but an outfit that exudes it can. In my first job, I spent a day in Burberry's awe-inspiringly sleek headquarters in central London. I was young, I was new to the industry, and the last thing I wanted to do was give any sign that I wasn't equipped for the job. Half my monthly salary was sunk into a silk dress; years later, that sense of certainty that my outfit was appropriate still seems like a worthy investment.

Edith Head, a costume designer who brought iconic glamour to stars that included Audrey Hepburn and Grace Kelly, knew a thing or two about dressing for the part. Update Edith's brand of Old Hollywood glamour with the assertive style of Samantha in Sex and the City and you've got clothes that demand to be taken seriously. Repeat after me: leggings do not maketh the woman, but a serious power-b*tch outfit can take you anywhere.

If Monsieur Lagerfeld's words are true, I gave up long ago. And, while I don't wish to squeeze myself into a couture suit and fingerless gloves every time I leave the house, he raises a valid point — sweatpants are the ultimate expression of comfort over style. They're the socially acceptable solution to wearing pajamas outside, and the spate of trendy activewear brands now available has made it a habit even harder to break.

So what's the solution? For me, it's two-fold. I've started monitoring my fondness for a stretchy pair of pants, trying to limit it to days which actually involve breaking a sweat. And, when that proves too much, I've started buying athletic wear that could almost pass for real clothes. I haven't lost control, Karl — I've just lost the will to use a zip.