History in the Making

How to Dress Professionally When You Are a Millenial

There is a whole generation of us that are stuck in between- in between university/ education and true adulthood (according to what the Baby Boomers and Gen Y call true adulthood), in between leggings and sweatpants and suits and gowns, in between the formal workplace of yesteryear and the current dressed down nation we all now inhabit. Today’s post is all about striking the balance between youth and maturity in your professional wardrobe, and building confidence in your own sense of style.
How to Dress Professionally When You Are a Millenial

I am often asked why I am so dressed up; I don’t think I’m particularly dressed up- a dress or a skirt and top are just as easy to put on as pair of pants. (I would actually argue that a dress is easier, but that’s a discussion for another day.) There are a few reasons I dress the way I do, though. 1) I think that we ask too much of our clothing, and are far too hard on it; we should not expect the same pair of pants to take us to the office, to the gym, out on the weekend, on vacation, and anywhere else we please. It’s one pair of pants, not a magic lamp. Having clothing for work, and for play, and for athletics, and whatever else I need, helps my clothing last longer. 2) I think that being ultra casual does affect your mood and work ethic whether you want to admit it or not, and for me it makes me complacent and tired. 3) I enjoy it! 4) Dressing casually can make people think you are younger than you are, which doesn’t exactly help all of the time.

1) Leggings Aren’t the Perma-Answer

Yes, I am starting off blazing here- I do not believe that leggings should be the answer to every wardrobe question, or even a minority of them. Are leggings comfortable? Yes. Can other clothing be as comfortable? Absolutely. I know that a lot of people cling to leggings when they have gained weight- I myself am carrying extra weight currently that I wish I wasn’t, and it would be incredibly easy to slip into leggings every day. There are a few issues with that, though.

If you only wear leggings, you may not realise that the rest of your clothing is tight and uncomfortable. When you actually do need to wear something other than leggings, you are screwed (to be indelicate). Go and buy yourself clothing that fits instead of solely wearing the same two pairs of leggings non-stop; it doesn’t have to be an entire wardrobe but a buy a few pieces that fit properly (whatever size that is, because it’s just a construct), and make you feel confident.

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Via Pinterest; Comfortable but casual to the utmost

Take a step up a notch, and back away from the leggings for a bit. Teacher, parent of toddlers, woman who works 3 jobs, there are comfortable, durable, flattering, easy-to-clean items that aren’t leggings!

2) A Suit is Too Much

Unless you are in a specific industry or a professional carer, a suit probably isn’t needed. In fact, it is probably too much- I am all for dressing slightly above the norm, but a suit is usually overkill. I find that the business and office world is a difficult walk for most of us women currently. Men can still go with dress pants or slacks and button up shirt but us? There is the leggings and tunic look but that can be overly casual, women’s dress pants can be impossible to find (because we don’t get the waist measurement/inseam measurement option that men do), and a women’s suit looks incredibly formal. (If that is what you want, more power to you!)

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Via Pinterest; Perhaps on the formal side for every day work wear now

I also look quite young, and the formality of suits often does make me look far younger than I actually am. When I want people to take me seriously in my career, the last thing I want is people thinking I am playing dress up. I also find that if no other women in your office are wearing a suit, you will often stick out in an uncomfortable way. It’s almost as though we are limited by the sheer volume of choices!

So, How to Walk That Line?

Whatever your own style is, work within it! I skew very classic and traditional in my wardrobe, but these tips can be used for any wardrobe style.

1) Clean and Ironed

No matter what style of clothing you wear, dirty and wrinkled clothing is appealing to exactly no one. Get into a habit of hanging your clothing instead of throwing it in the dryer to eliminate a lot of ironing, and iron your clothing before putting it back in the closet so it is already ready to go. No one has ever said, “that person is too clean and neat for me”!
3_4 sleeve shirt

2) Err on the Side of Simple

I would personally recommend erring on the side of simple rather than busy. That isn’t to say that you can’t have personality in your outfits and statement pieces to make an outfit your own, but a busy and chaotic outfit can often say, “I’m young and trying everything because I don’t know what I’m doing.” I’m not claiming I know anything by a long shot, but I think that the older we become, we try specific things (instead of throwing many things to see what sticks.) A simple but bold outfit can carry a lot of confidence and weight with it!
Smart Set A-line Black and White Dress.jpg

3) Use Structured Pieces

I know that it can be a comforting tendency to wear loose, unstructured clothing when you don’t like your size or shape, but a little bit of structure gives an outfit direction and strength. I would balance structured with looser pieces, so that you still feel comfortable and don’t fall into the overly structured suit trap. (As someone who works in a university, I would say that in a majority of cases, you can tell who is a student and who is a staff member by how unstructured their clothing is.)
Vero Moda Black Blazer

4) Know What Works For You and Use It

We have all different things that suit us. Some of us look great in bright colours, some of us look fantastic in loud patterns, some of us can rock a black tux jacket like nobody’s business. But very few of us can do all of this, and that’s a-okay. I am absolutely more confident a piece that I know “works” for me than a total roll-of-the-dice piece. While I advocate identifying and using your style icon, make sure that the clothing you wear works for you and your body.

What do you want your style to say about you? 

Until tomorrow,
The Historian
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24 thoughts on “How to Dress Professionally When You Are a Millenial”

  • I am 60+ and still working, and have and never will be a casual office person. I, for instance, do not own jeans, and will never ever wear that to work, not leggings. That does not fit into my wardrobe for office wear. I only wear a dress, or a skirt and a nice top, and ‘casual’ jackets and nice decent shoes or sandals in the summer. I am also not a flip-flop or sneaker office person. Maybe I am old school, but that’s just me.

  • Great tips… I’d never dream of wearing leggings to the office! I agree especially with your point about structured pieces. I think that well fitted (not tight) clothing always looks polished and can work on just about any body type.

    • I’m not sure when leggings became the “norm” but it really seems like they have, unfortunately. I do understand that the drawback of fitted clothing is that weight loss and gain means that you do need more tailoring, but I think that that isn’t a bad thing!

  • I used to hate having to wear suits because I felt so awkward in them. Took awhile to find my style for a professional work environment. Great advice!

    • I do struggle in suits- I am quite a petite person, and it’s difficult to find a suit that is a) petite and b) not “too old” for me. Unless a suit is strictly required, I recommend playing around to see what is comfortable for you!

  • I feel the same way about leggings! I own a few pairs but they are definately house leggings only haha 🙂 I started placing a focus on a more professional dress at the beginning of the year and it’s been great! It’s crazy when you realize that you have been dressing without putting a lot of thought into it this whole time. Great post!

    • I have 3-4 pairs of Lululemon leggings that I’ve had for years, and I love using them for yoga, for walking my dog, for house work… NOT for work! And it really is surprising when you stop and look at your wardrobe and what you were throwing together without thought, and then realise what a difference a little bit of thought can make! Thank you 🙂

    • It’s just not appropriate- leggings are NOT always the answer!! And finding a good pair of black pants that work for you is key for not only your professional wardrobe, but casual as well- you will ALWAYS use them 🙂

  • Your rant on leggings is sooo funny. One of my many hats is a teacher at a really small, cooperative school of home schoolers. Ninety percent of the moms are leggings, all day, every day.
    And I get flack for dressing up a little. But I feel like it’s important to create a bit of a barrier when I teach high schoolers. Distinction between myself and them. Clothes are an easy way to give a visual cue, I am not your classmate.
    I find that increasingly important with every year I teach. LOL

    • That’s exactly it- I work at a university and it is so easy to be mistaken for a student. And because a student can be of any age at a university, being older isn’t a clear indicator you aren’t a student!
      When I have time at home, I have comfortable clothing to wear that isn’t leggings- it’s not THAT hard to find clothing that isn’t!! I will say it- I don’t take you seriously if you live in leggings. If you aren’t going to put effort into your appearance ever, how do I know that you will put effort into anything else?

    • When we dress we send out a message – a visual cue if you like. This could be anything from: I could not care less about you or about myself for that matter therefore I barely bothered to wash, to ; hey look at all the pile of expensive clothes and accessories I managed to combine in one outfit.

  • Being a plus-sized person, I have always stayed away from leggings but over the last year or so I’ve fallen in love! Not with like actual legging-leggings (if ya know what I mean) but with hybrid leggings. Especially as I have been dropping weight. I have “jeggings” which are more jeans than leggings, but I can get a smaller size or a snugger fit, and know that they will stretch a little bit over my body and last longer because they won’t feel loose as quickly because of the stretch. I can’t go the full-on legging route like yoga pant type things though. I always say that if the material can support a pocket but it’s more of a pant than a legging and it’s ok haha.

  • Truer word was never spoken! I agree with all your points above…. brilliant post. I am going to prepare a post on my blog about the return of dressing up. Not ridiculous dressing up , but wearing actual clothes as opposed to sweatpants…

    • Oh, I am so excited to read it- please comment here with the link when it’s up so people can go read it!! I’m wearing sweatpants right now- before 7am on Saturday right after I walked my dog…. not doing things out in public….

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