The Do’s and Don’ts Of Work-Occasion Dressing

OFF-SITE EXCURSIONS: All business-related events, no matter how casual—team-bonding activities, brainstorming retreats, etc.—still require a professional look. 

Don’t:  Don anything extreme, such as cropped tops, tight gym shorts, ripped clothing, worn-out jeans, sweats, or tees with controversial or political messages. 

Do: Take a step down from your usual work look—if you normally wear a suit and tie or dress and heels, think a stylish button-down with nice pants and a blouse. If that is your daily look, consider a polo shirt or nice top with tailored  jeans.

Men: Try a button-down with contrasting cuffs and collar; wear with khakis or dark-wash denim and a pair of stylish shoes. 

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Women: A ponte-knit fabric pant looks polished yet allows for easy movement. For a more casual look, try leggings or straight leg, dark-wash jeans paired with a stylish tunic or another long top. 

GOLF OUTING: Golf is a game that’s steeped in tradition and, not surprisingly, has strict rules about appropriate attire, whether you’re playing at a fancy private club or a public course. 

Don’t: Try to get away with T-shirts and other collar-less tops, street shoes, jeans, sweat pants, or ultra-short skirts. 

Do: Wear soft-spiked golf shoes and golf clothing—it has detailing like required collars, front pockets for balls and tees, and fabrics with sun protection. Overall, keep it simple with regard to color and patterns—this is not the time to stand out from the crowd. 

Men: Collared polo or golf shirts paired with golf pants or golf shorts and hat. (Many courses require tucked-in shirts, so don’t forget a belt.)

Women: Collared golf dresses or collared shirts paired with golf skirts, pants, or Bermuda-length shorts, plus golf hat or visor. Culotte-style skirts with built-in nylon shorts are especially comfortable and not too revealing when swinging a club.  

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WORKING ON THE WEEKEND Again, think casual but office-appropriate. When in doubt, go a little more traditional—you’re still at your workplace and not working from your couch.

Don’t: Come to the office in too-casual attire such as workout wear, gym shorts, sweatpants, flip-flops, cropped tops, leggings with short tops, or exposed bra-straps. 

Do: Dress as though you might bump into your boss—you very well might. The trick is to look professional while not too stuffy. 

Men: Button-downs, new-looking jeans or khakis, and rubber-soled shoes. Fabrics can be casual, such as a denim shirt, but cuts should be tailored. Creatives can think more out-of-the-box with colorful button downs or graphic T-shirts.

Women: Make changes to your regular attire—wear shorter heels or flats if you usually wear high heels, separates if you always wear suits, and pants (see off-site recommendations above) if you typically wear dresses. Add stretch-blend tops—they’re comfortable and move with you yet are more attractive than tees or sweatshirts. Leggings should be thick, opaque, and resemble pant fabrics and absolutely worn with tops that cover the derriere.   

FLYING ON A BIZ TRIP: The trick here? To be comfy—but not look it.

Don’t: Travel in sweatpants, tracksuits, pajama-style outfits, or fuzzy slippers.

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Do: Be comfortable without looking sloppy. And dress in layers to accommodate changes in temperature in the terminal and aircraft. 

Men: Traveling solo: dark-wash jeans, T-shirt, sweater, or nice hoodie plus stylish sneakers. With the boss, clients, or colleagues: khakis, a button-down, classic blazer, and loafers.

Women: Tailored pants in a stretch fabric, dark denim, or leggings. Pair with sleeveless or short-sleeved long-knit tops and add a wrap-style jacket or a soft pashmina to double as a blanket. For footwear, check out the versatile KaraMac line designed in Mount Kisco; it offers different embellishments and heel covers to create several looks from each pair. 

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