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Work to Play or Play to Work? Lee Ann's Short Term Investment

Updated: Sep 4, 2019

Work to Play or Play to Work? Lee Ann's Short Term Investment

I am jealous of my husband.

Barring awkward patches of chest hair and his booming but innocuous morning farts, I would happily trade places with him.

“But Kat, you have such soft hair and an incomparable command of flowery prose, why would you want to trade that in for the backside of a sponge (what some refer to as a boy)?” you ask.

Well, men have it easy when it comes to getting dressed, particularly easy when it comes to transitioning from work attire to play. It seems with very little effort my husband can enter a business meeting and be ready for date night with the power of Old Spice and the cuff of a sleeve. That’s enough for me to shake my fist at the heavens and demand “Tradesies!” at least twice a week.

And unless you also find yourself with awkward patches of chest hair and booming morning farts, you may too feel a bit confused for how to seamlessly transition your look from work to play. Fret not; I have cracked the code, and it doesn't require you to wear a blazer over top of your dinosaur onesie. I spent a day of playing dress up with a woman who works and plays and works and plays again – Lee Ann Moyer, entrepreneur and owner of the Portland’s Mom Blog. Lee Ann wears many professional hats and is also required to run, crouch and chase as she is also a busy mother to 4 energetic little humans. I set her up with a Short Term Investment styling package, focusing on finding outfits that would seamlessly transition from role to role throughout the day.

Lee Ann Moyer wearing vintage wrap dress looks

Look 1: The Wrap Dress

As you may have seen from my other blog post, I’m a huge fan of wrap dresses. Here we have paired it with black ankle strapped heels, making Lee Ann a force to be reckoned with for client meetings, speaking engagements and conferences alike. To transition this look into something that is appropriate for play, like a romantic-but-casual date night with her husband or a stroll to an evening farmer’s market, the goal is to soften the look with a midi sweater and a detailed belt along the waist. The sweater itself is so unapologetically soft and conjures feelings of comfort and relaxation. The detailed belt adds visual interest and defines Lee Ann’s waist to balance out the softness of the cardigan with the slightest hint towards her curves. Finish the look off with a pair of nude shooties and this lady is ready to paint the town red. The key to transitioning a wrap dress is softening the ensemble with a soft layer, such as a midi or maxi cardigan sweater.

Lee Ann Moyer wearing grey blazer looks

Look 2: The Boss Lady Blazer

Business casual takes on a different meaning depending on your geographic location. In Michigan, it meant khakis and a button up; in Portland, it means jeans and tennis shoes. I remember the utter shock I was in when I went in for a coveted job interview in Portland to find that the head honcho herself was clad in a pair of relaxed fitting jeans and New Balance tennis shoes. Ah, Portland. I will never be ok with wearing tennis shoes to a corporate work environment, not even on a casual Friday. My 4-year stint in Michigan has brainwashed me and for now, I don’t think I will ever think differently.

For Lee Ann’s look, we went for business casual incorporating a tailored blazer with the slightest bit of shoulder padding that adds stature to Lee Ann’s frame. The patterned navy top adds visual interest and disguises any wobbly bits while the dark washed skinny jeans elongate her gorgeous leg line. To finish it off and as a nod to the free and fun nature of Portland’s super casual take on business casual, I cuffed her pants and had this lovely lady strolling around in a pair of low ankle sandals.

To transition into play, we have taken away all the pattern and opted for a monochromatic layer beneath with a silky black top and black pant leggings. This monochromatic ensemble creates a crazy long unobstructed leg line, making Lee Ann look model-esque in all of her height and glory. Additionally, the monochromatic ensemble mimics an adorable jumpsuit, oozing feelings of play, margaritas and happy hour festivities. To complete the look, I have added a fun bohemian choker necklace and a pair of neutral shooties. When thinking about how to transition your blazer for play time festivities, a monochromatic base layer, draping necklace, and edgy pair of neutral shooties will get you there faster than a stick of Old Spice deodorant.

Lee Ann Moyer wearing blue trench looks

Look 3: In the Trenches

This is perhaps my favorite look on Lee Ann. The sky blue trench coat is a timeless piece that adds structure and polish to any outfit. When I see it on Lee Ann, I am tempted to sing in falsetto, snap my fingers and belt out the most tone-deaf rendition of the Isley Brothers’ “Who’s That lady?” that I can muster. This coat just makes you take notice of whoever is in it. To accentuate Lee Ann’s gorgeous leg line (this lady has legs for days,) I have opted for a checkered, black and white pencil skirt that sits close against her skin and accentuates some lovely curves. We have completed the outfit with a white tank tucked in that serves as a neutral pop of color. This classy look is perfect for any of Lee Ann’s client meetings. To transition this outfit for non-work activities (think a very classy grocery store trip or a parent-teacher conference), we went the route of tank and jeans. For this transition, we traded her skirt for a pair of dark-washed skinny jeans, tucked in the tank top and kept the same ankle strapped heels. When thinking about how to make a trench play time appropriate, a tee shirt and jeans as a base layer will never fail you.

Work To Play or Play to Work?

It seems the transition from work to play can actually be as easy as Old Spice and a cuffed sleeve, if not easier. You will get it right every time when transitioning your attire if you think more about your outfit’s balance rather than individual clothing items. A work blazer begs to be neutralized with a fun jumpsuit, and there’s nothing a trench coat loves more than a pair of fitted jeans and a tucked in tee. Often times finding the compliment to your outfit’s feature piece is all you need to soften or sharpen the look for your next work or play adventure.

If you enjoyed seeing the results of Lee Ann’s Short Term Investment package, there’s no time like the present to invest in your own look! Throughout all of May 2019 I’m taking 20% off all of Seven’s styling packages, including the Short Term Investment package. This package is the perfect way to get your feet wet with personal styling – schedule your free consultation today!

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May 09, 2019

Hey Healerword! Awwww.. I love that you are picking your style crush via my mama makeovers, I am so very flattered. I adore Lee Ann's looks and I am so glad to hear they resonated with you!


May 07, 2019

I didn't see this one from earlier on in the week, but just as lovely. I think its so amazing how these are two completely different women and you have given them two completely different looks. I love both, but I think Lee Ann's is more of my style.


May 05, 2019

Hey Lisa! I absolutely concur, this baby blue trench on Lee Ann is the perfect addition to any Spring wardrobe.


May 03, 2019

I have been looking for a trench coat just like the one she's wearing, I think they are perfect for Spring.


May 02, 2019

Hey itshellgarcia, Yes, you are correct, makeover magic strikes again!

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