Remember back in the day when women considered proper work wear to be from labels like Liz Claiborne and Petite Sophisticate? It’s also interesting to note that, say, ten years ago, women made a very clear distinction between their professional wardrobes and their “casual weekend” wardrobes—a reference that undoubtedly pulls light wash denim, chambray button downs, and, gawk, open-toed sandals to mind. As almost any flat-form-or-loafer-clad professional working in the fashion industry will confirm now, fashion changes a lot, and very quickly.

Today, the distinction between what a professional wears to the office and what he or she pulls together for a Saturday brunch are nearly nonexistent. Style, from within fashion conscious cultures like New York, Los Angeles, and D.C., is fluid. A leather motorcycle jacket is no longer perceived as an edgy layering piece for a club night. It’s now a third piece topper meant to join that dark wash chambray shirt or popped over a cashmere turtleneck and a skater skirt. Depending on a person’s given work environment, this outfit would be totally acceptable, and may even win her points for style from her colleagues.

Addressing the former generation’s need for a conservative professional wardrobe, the options for updated and trendy styles suitable for a neck collar environment are definitely out there. Subways are perhaps the most effective way of gathering observations of a now fashionable millennial generation working in finance, technology, and law. The navy and pinstripe suits denote Deutsche Bank and Watchell, but the various polka dot socks peaking out underneath those suits, paired with speckled ties and mahogany wingtip leather oxfords, are perfect indicators of fashion’s fluidity, from day to night and Monday to Sunday.

As a fashion player myself, I’ve checked in with a few present and former colleagues and asked them about the way they manage their styles throughout the week.

Here’s what they had to say:

photo (80)Michelle Chuang, Digital Marketing Manager, Tibi

Michelle is wearing: MMM x H&M sweater, vintage silk stripe trousers, and Tibi ‘Leona’ heels.

AG: I’m always fascinated to learn about the process of dressing, particularly of making that style transition from corporate day to drinks and dinner evening. How do you approach selecting versatile pieces?

MC: Comfort is king. I always think about how my clothes will interact with me throughout the day. Luckily for me, strategy works well with the over-sized silhouettes I generally gravitate towards. I never say no to a voluminous dress, pops of red, [monochrome] white shoes, French grocery net bags, and great socks. I try to avoid fancy handbags, unless they’re the ones crafted by my friends at M2Malletier.

unnamed-1Jhonathan Mendez De León, Luxury Public Relations Consultant, New York

Jhonathan is wearing: Tom Ford coat, YSL vest, Lanvin shirt, Burberry pants, and Tom Ford specs

AG: Your style is impeccable and very personalized. That’s a hard attribute to accomplish on a daily basis. How do you do it?

JML: [I’m] Manhattan-raised, so naturally, I have one of those sordid Gossip Girl prep school stories that has inspired both my style and its evolution. I was also moving from one internship to another—Yves Saint Laurent, Louis Vuitton, Hermès, and finally, Tom Ford. Being around all these incredibly cool people, I was able to pick and choose what bits would eventually help me create who I was sartorially. [Thus], I had tapped my core essence—a little street and a little 5th Ave. I [also] didn’t want to exclude the element of exoticism and street from my homeland [Dominican Republic] in my quest for luxe alpaca sweaters, a smart jacquard trouser, and my favorite crocodile loafers. #Normcore is a part of me now, but I just can’t give up the Tom Ford. Too many bowties to just leave behind collecting dust! My goal is to keep surprising (even those who know you)!

10534943_531221087007758_1477301858_nMaide Graebin, Head Designer, Kelsi Dagger Brooklyn

Maide is wearing: Urban Outfitters crop top and skirt, Persol sunnies, and Jamis Beatnik bike

AG: You always dress to the brand, KDB. What’s your take on dressing, not just for one specific environment, but as a lifestyle?

MG: I’ve lived in so many places—traveled quite a lot—and every single culture I experienced [has] had a big influence on my personal style. Working in fashion, I am exposed to constant new trends and creative people, usually with unique outfits. I definitely say that my way of dressing is always changing, evolving. I feel that I’ve developed a personal look that makes me feel comfortable. There are two rules to live by when it comes to dressing, and the rest is usually very easy to figure out: feel good (self esteem is the best outfit one can have) and [wear] great shoes—a nice pair of shoes makes even a potato sack look cool.

– Alexandra Gamez for The Untitled Magazine

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