9 to 9 Style: Working Your Wardrobe to Fit Your Life

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Have you found yourself leaving behind a conventional office and conventional schedule for a more flexible work lifestyle? For instance you might to go to a networking breakfast, followed by a late morning one-to-one, answer some emails, fit in a quick walk at lunch, make a few sales calls, let the dog out and join a client for an early dinner meeting, followed by coffee with friends. Whatever you put on in the morning needs to work hard for you all day and into the evening, and in all those scenarios. The more varied your routine, the more flexible your wardrobe needs to be to accommodate it. It’s the reality of 9 to 9 Style.

Saying goodbye to 9 to 5 Style and hello to 9 to 9 Style requires thoughtfulness and some planning, but it rewards you with an ease of use and versatility that is so vital to a busy lifestyle. When you’ve finished reading this you will know the key points of making a 9 to 9 Style work for you.


Key Items for a Woman’s 9 to 9 Wardrobe

(Don’t worry men. It’s ladies first, but I’ve got you covered. Keep reading.)

Structured Jacket: I’m always telling my clients that a good business casual Look needs at least one wardrobe “Spokesgarment” – the piece that tells everyone that you may be relaxed, but you’re here for business. A structured jacket is an excellent “Spokesgarment”. It can lend authority to a pair of nice jeans and a basic tee, or a feeling of grounding to a light summer dress.

Ponte Knit Dress: Sheath, shift, or fit and flare, a basic Ponte knit dress is a wardrobe chameleon that can take you from the playground to a downtown bistro with a quick change of accessories you can keep in your car.

Dark Wash Jeans: The workhorses of the Business Casual wardrobe, dark wash jeans can easily be dressed up for an evening out after carrying you stylishly through a day of business appointments and errands. Just remember to leave all distressing and embellishments out of it. You’re going for classic, not trendy.


Accessories are the transformers of the clothing world. They can take a simple dress and launch it into heights of elegance, or ground it in relatable comfort. Let’s consider what they can do for a knit dress:


Navy Sheath


This solid navy sheath has incredible possibilities. Let’s start with the 9 to 5 accessory Look.




Maintain work-worthy polish with pearl stud earrings, dressy casual shoes such as suede slim-line loafers (comfortable enough to get your walk in at lunch), a patterned scarf, and a gold (or silver) cuff bracelet.



Cuff bracelets are often better for women who work at least part of their day at a keyboard. They sit higher on the wrist and don’t clank annoyingly on hard surfaces, such as desks.


Now, to take this look from 5 to 9 all you need is a simple change of accessories.


Navy Sheath 5 to 9 Look


Remove your scarf and tie it on your handbag for a little pop of color there. Complement your pearl stud earrings with a pearl necklace. Exchange your loafers for dress flats or heels. To really polish off your Look, add a pop of saturated color on your lips.

Pro Tip: Matching the shade of your lipstick to the shade of your shoes is a great way to amplify the impact of your color statement. This works well with pink, plum and red shades… not so much with green, blue, and other non-traditional lip colors.


The same accessory swap can update a blazer, pants and cami Look. If your days are more formal and your nights more casual you can reverse the accessory swap to suit your schedule.

What to watch out for:

When you swap casual shoes for dress shoes, make sure that the heel height for both works for the length of the pants, or skirt you are wearing. The wrong hem length is a Look Killer!


Can I wear clothing like jogging pants that look like trousers to work?



Key Items for a Man’s 9 to 9 Wardrobe


Non-Wrinkling Button Front Shirt: If you want your shirt to carry you from morning until evening, you have to get one that has staying power – meaning one that won’t look like a rumpled mess by noon. You can have a traditional pointed collar, or a banded collar, but it has to be made of non-wrinkling material.

Lightweight Blazer or Sport Coat: Whether it’s knit, tropical weight wool, denim, linen, or seersucker, a lightweight blazer is an essential for pulling a casual look together.


Pro Tip: Always keep a blazer in your car, or office, ready for a quick image upgrade.

A friend of mine proved the worth of keeping a blazer handy when he was working in a casual office dealing with disaster preparedness. While he was there a call came that he was needed to meet with then-governor George W. Bush. There was a fair amount of panic in other parts of the office, but my friend just popped on the blazer he kept on a hanger in his office. His appearance was instantly upgraded. When his coworker was incredulous and said, “You keep a blazer in your office?” He replied, “Yes. For times like these.”


Dark Wash Jeans: A pair of well-fitting dark wash jeans can easily move between work, play and dress casual evening events.

These flexible staples can see you through most days in your 9 to 9 lifestyle. Semi-relaxed fits are okay, but don’t go too loose. A little fitting is necessary to keep things looking sharp.


Accessories play an important role in taking a man’s attire from a 9 to 5 Look to a 9 to 9 Look, just as they do for women. Let’s look at how they can transform these easy to wear pieces.




A non-iron button front shirt, cuffed three times, with a pair of dark wash jeans are a great start for a business casual 9 to 5 Look. Add a pair of leather loafers and a fabric belt and you are all set.

Now for a quick accessory change.



To take this Look from 5 to 9, add a blazer with a silk pocket square and swap your fabric belt for a leather one that goes with your loafers. Add a tie, if your agenda calls for it.

If your days are more formal than your evenings, you can reverse the accessory swap to suit your schedule.


Pro Tip: Take care of your leather.

Poorly conditioned, marked-up, or cracked leather doesn’t say “Boss” any more than wrinkles do. Invest the time to keep your leather well.

When it comes to your shoes, if they are a hard leather, keep them shined. If they are a soft leather or nubuck, get a chem bar to keep them scuff-free and clean. Foam “eraser” cleaning pads are great for cleaning scuff marks off rubber-soles.

If your belt begins to crack or show other signs of wear (not counting deliberately distressed styles) get another belt. Remember to check the condition of your leather wallet, as well.


The Midday Refresh

When your days blend into your evenings, it’s good to give yourself a boost to keep your visual spark to the end of your day. That’s where the Midday Refresh comes in. Sometime between 3 p.m. and 5 p.m. take a moment to take care of yourself.


  • Comb/brush your hair. The easiest of all refreshes.


  • Women – take your lipstick completely off and reapply it fresh. Apply fresh powder.


  • Men – splash some water on your face and neck to “renew your outlook” as Aunt Eugenia used to say. Skip adding more aftershave. Many men refresh their aftershave or cologne after lunch/midday because they’ve gone nose-blind to it. Guys, the rest of us haven’t.


  • Brush your teeth or swish with some mouthwash.


  • Stretch your back and neck. It can do wonders for your disposition and help you enjoy the rest of your day/evening.


  • Take a micro-nap, if you can. Just closing your eyes for a few minutes can help you recharge before taking on the rest of your day.


Your varied and busy lifestyle doesn’t have to mean hauling around a complete change of clothing for each new appointment. Versatile pieces and well-chosen accessories can help you create a wardrobe that flexes with your day, from 9 to 9, with ease.


Are you ready to see where a well-crafted image can take you? Let’s talk.







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