Lots of Career Advice + What to Wear to Work This Summer

May 28, 2019

Summer Work Wear I wit & whimsy

I’ve always been extremely motived when it comes to my career. I think it is one of the characteristics that allows me to work for myself. While I don’t have a boss anymore, I rely heavily on my own determination to ensure I’m succeeding. In my recent reader survey I had several inquiries about more office-friendly outfit recommendations and today I’m excited to share them with you along with some of my best career advice from a 12-year career. I’ve also crowdsourced career advice from some of my friends and former colleagues and I hope you’re left as inspired and motivated as I was reading through all of the wisdom!

Summer Work Wear I wit & whimsy

Summer Work Wear I wit & whimsy

Summer Work Wear I wit & whimsy

Summer Work Wear I wit & whimsy

Summer Work Wear I wit & whimsy

Some of my best career advice:

  • Always over-deliver. Do what’s been asked of you and then do more. It will make you memorable.
  • Be extremely detail-oriented. Have you double checked your work before you submit it? Is the formatting perfect? Have you gone above and beyond?
  • Think differently. Sure, there’s ways that things may have always been done in your line of work…but is there a better way you can propose? Fortune favors the bold.
  • Be resourceful and be a resource. Don’t ask questions to your manager or a higher-up if you can easily find out the answer in a different way. And become the person they feel they can go to. For ideas, for help – you name it! Being a reliable, go-getter colleague is a way to set you apart.
  • Remember that some of your most stressful or overwhelming projects or clients will be the ones that are defining moments in your career. They’ll often be the ones you come to reference for years to come when you need examples of your work. Push through and remember things will always improve and you’ll be grateful for the experience in hindsight.
  • Follow through. I can’t believe how many people I have managed or mentored over the years who ask for guidance or help and then never circle back to say thank you or to tell me how circumstances net out. They ask for my time reviewing their resume, making connections, being a reference, taking a meeting to get help, etc. etc. etc. And then I don’t hear from them again. If I get a lead or a referral from someone I always look to remember to go back to the person who recommended me to thank them, give them a little gift or a referral bonus of sorts. Much of your career will be guided by who you know and people always remember how you made them feel.
  • Trust your instinct. This has been a guiding light for me in self employment because I have less people around to help gut-check me but it has been a powerful lesson. If something doesn’t feel right, figure out why. Don’t take the job just because you think you should or because it looks great on paper. What does your gut tell you about the job?

The best career advice from people I know:

  • Be true to yourself and set boundaries early. Work will take advantage of how much you give, so decide where your hard lines will be and don’t budge from them. Want to make it to the gym a few days a week? Block it on your calendar like you would a meeting and don’t compromise. You are in charge of your own work/life balance. Also ask for feedback at every opportunity – do it until you annoy your coworkers. Craving feedback – even for the littlest things – will help you grow and find new opportunities to stretch your abilities. (Andrea S.)
  • The best career advice I’ve ever gotten was from my #1 career and life coach, my dad. Early in my career I was thrilled to be working in an office that was primarily run by women and had fantasies of being nurtured and mentored by all of these talented, successful, professional women. So it was a huge disappointment when a few of them wanted little to nothing to do with me (a 22 year old intern, can you believe it…!) I remember my dad saying to me at the time, “one day you’ll be someone’s boss, and you can remember this moment and use it to help you decide what kind of boss you want to be.” It is advice I took to heart and advice I have given often since then. I have chosen to try and treat everyone I work with and manage with compassion and respect. You never know where people will end up and as much of business is built on relationships, it’s helped me foster and invest in people who’ve ended up becoming important partners, clients, and members of my extended network of super smart, talented women. (Erin F.)
  • Before you send an email, ask yourself: have you anticipated and answered any question that could arise?  Have you included all of the necessary details?  People are so quick to react, they don’t think things through, which leads to 200 unnecessary back and forths. Take a beat to go through your points and ensure you’re thinking 5 steps ahead for the recipient on the other end – especially if it’s your boss – before you push send. Additionally, no matter what task you’re assigned – ace it. Never be too big to do the smallest job in the room. I’m almost 20 years into PR, and I can compile goodie bags and create press placement reports with the best of them.  Yes, experience often means you don’t have to do the more menial tasks, but you should always know how to do them and not let your ego get in the way of you helping when help is necessary. (Jaime M.)
  • No one is going to give you what you want unless you ask for it. Over the years I’ve sometimes naively assumed that bosses would give me more money, responsibility, autonomy, etc. without me having to ask or have the uncomfortable conversations. But the truth is that no one is going to fight those battles for you or do you any favors. You have to speak your mind and ask for the things you want and deserve. (Hailey T.)
  • There is a Billie Cox quote that the former President of my company once referenced when talking about her own career and advice to live by, “the two things in life you are in total control over are your attitude and effort.”  (Jenny R.)
  • “Own it”. Good or bad. Think you have a good idea but aren’t sure? Own it with conviction. Messed up? Own it but make sure they know your intention. (Alyson B.)
  • Mistakes are going to happen and things will go wrong. What I’ve learned is that it’s not worth stressing about what has already happened.  Instead, handle it quickly and focus on how to avoid the same situation happening in the future. (Annie M.)
  • Put in the time at the beginning to avoid overtime at the end. Aka: be detail-oriented and ON every project from the start so that you don’t have to waste time correcting mistakes and problem solving at the end. (Sarah B.)
  • Your energy is contagious! Be aware of how others are perceiving you and how you want to be perceived in the workplace. Also: Create boundaries and find balance. Your sleep schedule, waistline and sanity will thank you. (Angie T.)
  • A good reputation is hard to build and easy to destroy. And create a seat at the table. Bring ideas, talent, and strong work that add value. Don’t just fill the position—make people rely on you for the value you add. (Rachel Z.)
  •  “I believe in myself so much that I make others believe in me.” This has become my mantra and I like that it levels up “fake it till you make it.” (Zoe C.)
  • Be the person who is willing to say, “you have spinach stuck in your teeth.” In other words, don’t be afraid to give feedback in a work setting, even if it’s to your intimidating boss. Any real professional wants feedback to grow, and anyone who blows up at you for giving feedback is not worth working for. I have never met a person who doesn’t want to know there is spinach stuck in their teeth! (Bekka P.)
  • You quit your boss, not your job. Who you work with is SO important! (Jill C.)

Hope you guys find the above inspiring and helpful…now onto workwear!

While most days I am pretty casual working from my apartment or my co-working space The Wing, I also regularly have in person client meetings or attend events where I want to be more formal. My number one rule to getting dressed for meetings? I want my outfit to represent myself and my brand. This means not dressing for how I think I *should* dress for certain work environments. I want to always be appropriate but also be ME. I remember that as I was graduating college and looking for entry-level PR jobs someone told me I needed to dress for the job I wanted in the environment I wanted. When I looked at PR firms hardly anyone was wearing suits. So, instead, for every interview I wore a pair of black cropped pants, a white button down or a sleeveless silk blouse and a pair of pumps that made me feel confident. It said “I’m here for a job” but also “I’m not cookie cutter” or just trying to look the part.

For a little summer work wear inspiration, I teamed up with Ann Taylor who has long been my go-to for outfits for important meetings. I absolutely loved styling the Ann Taylor Wide Leg Marina pant and in the white it is such a great summer alternative when you tire of wearing dresses or black pants. These pants are so comfortable and if you’re less risky and would prefer to steer clear from white pants, fear not! They also come in loads of additional colors (I’m going to buy black because I love how they look so much!)

A few other summer workwear outfit ideas:

  • If your office lets you wear jeans, I think there’s nothing more chic than a great pair of denim paired with a tweed jacket or simple blazer and a pair of great pumps or kitten heels. I love the one I’m wearing in the above photos because it adds a fun dose of color but this white one is also so my style. It would also pair well over a sheath dress or a striped tee.
  • If you can’t wear jeans to the office, give yourself some license to play with work pants in a variety of colors but a classic style like these.
  • When it comes to tops I personally always look for ones that can do double duty. I want ones that can be worn to work but also could work for “off duty” style. For example, a versatile silk cami that’s great at work under a blazer or tweed jacket but perfect for nighttime when worn with jeans and a leather jacket. Also love this sleeveless sweater and this button-back shell.
  • If you want to up the cool factor of a shift dress, try adding a moto jacket like this one.
  • Speaking of shift dresses, look for ones with special details or versatility. This one would be great for a hot day in the summer at the office but you could also make it work for a bridal shower or baby shower or a more casual wedding if paired with the right accessories.
  • If pencil skirts aren’t for you, try a wrap skirt style like this one. I love how AT styled it with a buttoned up cardigan! (I bought the cardigan because we all know how I love a midi skirt!)
  • If you want to up your shoe game, Ann Taylor’s shoes right now are SO GOOD. I love the suede version of the shoes I’m wearing in this post, these darling bow heels, these sandals that are great for work or weekends, these sandals with pearl details (you know I love a pearl detail!), these heels with stylish scallop detailing and these versatile heels.
. . .

Ann Taylor Wide Leg Marina Pants (wearing size 4) // Ann Taylor Shoulder Tie Sweater Tank (wearing M), Ann Taylor Fringe Tweed Jacket (size 4) & Ann Taylor Leather Block Sandals (tts & so comfortable! Also come in black) // Cluse Watch

p.s. you can explore all my past career-related posts here.

This post is in collaboration with Ann Taylor. Thank you so much for supporting the brands I love to work with!

[Carter Fish Photography]

what I'm wearing

18 comments on “Lots of Career Advice + What to Wear to Work This Summer”

  1. I can always count on you for the perfect advice and the perfect outfit! Thanks for this post—it’s always so hard to find the right wear-to-work looks and still feel like myself. I also love all the advice from strong career women. Thanks so much for sharing with your readers!

  2. You look amazing in this look! I appreciate hearing your advice and how you were able to be confident enough to work for yourself. Do you mind sharing where your purse is from? I’m looking for a structured satchel, and yours is to die for! Thanks in advance 🙂

  3. Love reading these wonderful pieces of advice from such an incredible group of women. Also love the outfit inspo! Such a perfect time to gear up on a new summer work wardrobe.

  4. love the marigold top on you! yellow and marigold are my FAVORITE colors for spring and summer, that’s when I know warm weather season is here!

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