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10 Pieces That Never Go Out Of Style

Photo by BG002/Bauer-Griffin/GC Images, Photo by Jeremy Moeller/Getty Images, Photo by Edward Berthelot/Getty Images, Photo by Jeremy Moeller/Getty Images

I started working in fashion fresh out of college. Lacking legit credentials, I’d sneak into shows in the early ’90s when Linda Evangelista, Christy Turlington, Claudia Schiffer, Naomi Campbell ruled the runway. It was heaven. Because I’m slightly neurotic and tend to look at fashion the way a doctor examines an X Ray, I started taking field notes on my personal style icons sitting front row at the shows (like Madeline Weeks at GQ, Carolyne Cerf de Dudzeele at Vogue, Isabelle Dupre at Elle). Years later, when I was named editor-in-chief at a  fashion mag, I found myself traveling to Europe for the shows alongside those women, essentially the most stylish on the planet. And I never stopped taking notes. One thing I loved to study was how they packed for three intense weeks in Milan, Paris and London. Here’s what I learned: Every good fashion editor, off-duty model and celebrity in full stealth-mode reaches for the same timeless pieces. Here they are:

1. The Trench Coat

My style magnetic field is the Paris Girl: Jane Birken, Inès De La Fressange, Alexa Chung (honorary, she’s from the UK), and most recently Alicia Vikander in HBO’s Irma Vep (also honorary, but the series is set in Paris). My entire fall identity can be distilled to this single image from a scene in Irma Vep:

As seen above, your trench should be in khaki and cinched at the waist. My Commes des Garçon trench is so old, like from the last century, and I’ll never buy a new one. Future-proof your trench by getting the proportions right. Lapels should not be outsized, buttons should be in a camel tortoise, keep to the classic khaki color and always in a heavy-duty, waterproof cotton twill; function is a major part of the appeal. Length should be just below the knee (not longer, not shorter). Trust me, it stands the test. Beware the trendier versions. Lo, that silver, metallic-leather Marc Jacobs trench was super cute…until it wasn’t.

2. The Boyfriend Jean

Sticking with the Paris Girl theme, a good mid-rise boyfriend jean is nothing less than essential, the classic, straight-leg shape always holds up. I never get rid my old boyfriends (jeans, yo) until they’ve lived a full life that goes something like this: (1) wear them till hole-y; (2) patch holes with amateur embroidery and vintage fabric; (3) when patchery-to-denim ratio becomes too great, cut them off; (4) when tattered beyond repair, give them a hero’s funeral. 

3. The Print Blouse

Whenever I’m styling someone, I recommend a pretty, feminine button-down silk blouse. If you don’t have a lot of print or color in your closet, one of these blouses is a good place to start. Think colorful patterns, possibly with ruffles or a tie front. Brands like La DoubleJ and MSGM usually nail the look. It goes to work with a blazer, but I equally love print blouses paired with a high-waisted short, the shirt tied at the waist. My favorite is an old Tracy Feith silk button-down in bright blue with weird aqua-colored deer running across it. Always works. 

4. The Blazer

It instantly makes jeans office-ready and dresses up a pair of shorts and sandals for a weekend look. Fit-wise, I like a boxy cut; the Dad version here is a bit sexy with pushed-up sleeves.  A cotton twill material will give you layering options for spring, summer and fall.

5. The Neutral Ribbed Turtleneck

If you had a late Friday night, keep this outfit on ice for Saturday morning: ribbed turtleneck, trench, boyfriend jean, sunglasses, Stan Smiths. Easy, beyond chic, hangover proof. 

6. The Cargo Pant

Wear it with high-heeled boots and a pretty silk blouse or chunky sneakers with a tiny top and a bomber. Revel in all of your pocket options—so many places to store your phone and stash your lipgloss. And pardon the ASMR moment, but I forgot how much I love the sound of baggy pants swishing when I walk. 

7. The Crisp White Button Down

Keep it crisp (no coffee drips please), choose cotton twill and wear it untucked with jeans or layer it with a neutral tones. So many good ones this season. Stick with the conservative basic or try some of the versions here. I re-buy my white shirt every fall because I like it blindingly white. This year that means supersized, slightly sheer with long, buttoned cuffs.

8. The Leather Tote

When my son was a baby, I violently rejected the diaper bag. What? Because I’m a new mom I suddenly want to walk around lugging a black nylon bag with bright butterflies? I don’t think so. My solution was to buy another, even bigger leather tote, which is now working great as my weekend bag since my son is long out of diapers. If you can splurge on a luxe, thick leather with good fittings all the better—it will last for years.

9. The Bomber Jacket

The bomber makes the list because it comes back almost every fall. As I’ve said before, stay away from extremes–shrunken or balloon-y shapes are ultimately one-season wonders. My choice is a slightly oversized bomber in nylon army green. Ideal for the summer-to-fall and spring-to-summer transitions, wear it with shorts, cargos, jeans or a mini, along with a simple tee and maybe some lug boots.

10. The Classic White Sneaker

When I arrived at GQ many years ago, Madeline Weeks, the fashion director, introduced me to Stan Smiths, the king of white sneaks: That was in 1997. I have since purchased dozens of pairs. The Ellen Show came and went and I never relented: I wear them with everything from minis to jumpsuits. Likely you have a pair. If you don’t, might I suggest: 

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