Ask the Editor: An Outfit for the ‘Cool’ Boss

Aug 14, 2023

When you’ve been a direct report for most of your career, making the transition to manager is a challenge.  One of the most visible ways to send the “manager” message is with your clothing.  Dressing just a bit nicer than you staff can help visually remind people that you are their supervisor.  But what happens when your direct reports are all 20-somethings who wear t-shirts and sweats to work?

Dear Belle:

Last week, I was promoted to team lead for a marketing company.  Average age on my team is about 26.  We work for a lot of clients, but they never see us except on the occasional Zoom and it’s a pretty casual industry.  Hot pink Spandex was the most common outfit when the Barbie movie came out to give you some idea of how casual.

I’m in a bind because the other team leads are all 40+ and I’m 32.  They promoted me because they wanted the perspective of a younger generation on the executive team.  My boss dresses like Jenna Lyons and her boss dresses like Victoria Beckham, so everyone has style.  I tried to do a dressed up athleisure thing and I felt like the intern in every exec-suite meeting.  Can you help me plan a couple of outfits that work?

Best wishes, Mercy

I remember my first day as “the boss.”  I was 29 and looked fresh out of college.  Half of my direct reports were 22, the other half were women in their 50s.  It was a strange business trying to thread that needle with my attire.  A suit every day felt like overkill, and not wearing at least a blazer felt like a mistake.  So I understand that it can be tough to find a look that works for this new phase of your career.  But this should also be an awesome time, you got promoted and that’s fabulous, so let’s see what we can do.

This look found on Pinterest felt like a good place to start.  You probably have a few of the pieces already.  And even if you don’t, they’re versatile enough, that if this doesn’t feel right for your situation, you can still wear them in other ways.  I updated the style of jeans and made a couple of changes to bring the look into 2023, but my re-style is faithful to the vibe.

The Blazer // Who bought a plaid blazer in 2019?  Is it still sitting in your pre-COVID closet gathering dust?  This fall is a good time to break it out.  If you still need one, this Maje blazer is absolute perfection (I wish they still had it in all the sizes).  I also found this lighter, windowpane style, also from Maje.  For something more affordable, try this Belle and Bloom blazer or this Steve Madden one.

Plaid not feeling right for you?  This is an outfit that could easily handle a white blazer or a relaxed tweed one.  If those also don’t feel true to you, what about a leather jacket?  This pale mauve one from All Saints has been living rent-free in my mind for months.

The Jeans // These need to be wide leg to be on trend.  This Paige pair has the relaxed vibe of the mid-90s on lock, but with a higher waist than I saw in that decade.  I like the lighter wash and the light distressing.  Personally, I’m going to buy these J.Crew high-waist wide legs in a soft chambray (also in petite and tall).  For a plus-size option, try these Good American palazzo jeans.

The key to making wide legs work is that you need to have them hemmed for the shoes you plan to wear with them.  Take them in, pay the tailor.  Otherwise they look sloppy.  It’s an inexpensive alteration, but it makes a world of difference.

The Tee // The simple black and white tee in the inspiration photo is an easy way to do a graphic look.  This Favorite Daughter tee (they also have “Favorite Aunt” and “Favorite Sister“) is a hot, young brand with a similar appeal.  I also liked this Sezane heart tee (up to XXL) and this Claire V. “Oui” tee.  This would also be a good time to break out that Comme de Garcons tee that you bought on sale and can’t figure out how to wear.

The Sneakers // The old school, high top Chucks are always a solid choice.  But for me, this Cariuma brand is starting to take off, and I want to be the first one in my group wearing them.  Lots of cool color combinations and styles.  Same price point as Veja with a more modern feel.  It’s also an eco-conscious brand.

The Accessories // If you’re ever concerned that bringing the cool to work isn’t in your skill set, do it with your accessories.  You can be perfectly professional with your main pieces and then have the on trend bag, sunnies, and jewelry to raise up the look.  I chose this Maison Martin Margiela bag because it is undeniably cool and unique.  It’s also on sale.  If you’re looking for something more like the flag bag in the photo, try Madewell.

The sunglasses are Anine Bing.  They’re also on deep discount.  So you can get a more recent it girl brand for less.  The shape is a unique take on a classic aviator, and lots of different face shapes can rock a square rim.

Lastly, I finished the look with a white nail, mine with a little sparkle.  And this called for a red brick lip, not red, red brick.  This Laura Gellar choice is also deeply hydrating for when fall starts to zap your skin of all moisture.  Keep the hair casual and relaxed for this look.

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  1. Nadine says:

    To me, this is a situation in which it makes sense to cast aside the idea of a work uniform. As a new-ish manager who also works with students, I dress for my day and my audience. In practice, that can mean anything from leggings and t-shirts to MM Lafleur dresses and blazers, depending on who my meetings are with.

  2. Naomi says:

    Where should the wide leg jeans hit? I would love to embrace a wider leg – my skinny jeans are starting to feel uncomfortably tight on my calves – but I just can’t get them to look good, not dumpy. Any tips for how to wear them with different types of shoes?

    • Belle says:

      This youtube shows you where they should hit: just above the ground in the back, top of the shoe in the front. https://www.youtube.com/watch?v=ZyvGPIWYO5I

      I pick one heel height — usually a 1.5-2″ boot — and hem them for that length. That way I can wear them with shoes that height, but only shoes that height. I’ve been known to have two pair of the same jeans hemmed for flats and heels. This is why skinny jeans got so popular, they could be worn with any shoe.

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