What to Wear When You’re Not Sure How Dressed Up You Need to Be

What to Wear When You’re Not Sure How Dressed Up You Need to Be
An introduction to dressing like a social chameleon.

The hardest part of dressing well isn’t figuring out fit. Or how colors match. Or how much to spend on a specific item. These are things that can be picked up by doing a little bit of research (or sent right to you if you’re a Primer subscriber).

Those questions are the technical side of style, more of the science.

The hardest part is deciphering how casual or dressed up to be for any given event. Some things are predefined by culture – a traditional wedding calls for a suit and tie. A funeral, a dark suit and muted colors.

Some things, like a job interview, used to be easy but now require a greater understanding of the social nuances of an industry. While finance or other classic professions still call for a suit and tie, wearing that to a Silicon Valley startup or to a creative Los Angeles advertising agency (as I mistakenly did 10 years ago), shows the dressed-down interviewer you’re green and lack boots-on-the-ground work experience.

This is where the art of dressing well comes in. Being impeccably dressed doesn’t just mean your tie bar is straight and you have the perfect pocket square fold – it’s knowing whether wearing a tie bar and pocket square at all is the proper level of dressiness for where you’re going.

And that is something that’s very tough to pick up, specifically for places and groups of people that are new to us.

Your partner invites you to accompany them to hang out with some higher ups to celebrate a win after work. The first inclination would be to wear more professionally-minded clothing – but this is outside of the office, and the goal isn’t to get your partner a job, it’s to help prove their social fluency within the group to encourage greater work engagement and opportunity. So what does that mean? That means you don’t want to appear too stuffy. You want to look and feel cool, but dressing too casually could exaggerate the higher ups’ perception of youth and inexperience.

You’re attending a work conference – except it’s in San Diego. You’ve never been there but you know it’s a much more casual city than the one you live in. Do you still wear a tie? A jacket even?

You’re going on a first date to a bar that you’ve never been to. You need something that’s sharp and intentional but A) doesn't make you look like an old man who overdresses because that’s what he has to wear to work; and B) doesn’t make you look like a guy who never outgrew college and still wears t-shirts to everything. But on top of both of those things, this bar appears to be a fancier cocktail type place – which would lead to dressing up – but it’s new and trendy and this person seems hip so…maybe casual?

Have you ever showed up somewhere and you’re way overdressed? It makes us feel old and socially inept, and like we’re standing out.

Have you ever showed up somewhere and you’re way underdressed? It makes us feel immature and socially inept, and like we’re standing out.

Which means you’ll feel unconfident and embarrassed. A powerful example of the real message behind the sentiment “clothing makes the man.” People misread that and think it’s a shallow and consumerist message. It’s actually a reference to the confidence and courage feeling well-dressed in a certain setting builds in us.

“Ok, great Andrew, but I still have to get to this thing in an hour and I don’t know what to wear.”

Almost all of the men’s fashion styles and items we talk about on Primer are from the foundation of versatility. I like to refer to really versatile items like a pair of boots that can be dressed up or down as chameleon items. On a day to day basis, that’s smart spending, as you’re getting more wear for your money than you would from a pair of dressy-only boots.

But what happens when you create an entire outfit of chameleon items? Full on social cloaking. Blending in like a chameleon isn’t referring to wearing a uniform that looks just like everyone else – it’s about choosing items that look like the appropriate level of dressiness whether the venue ends up being casual or dressed up. Put an actual chameleon on sand and he fits in with sand. Put him in a jungle and he fits in with the leaves.

That’s the goal of this outfit. When you’ve got 30 minutes to get ready and you’re staring at your closet completely dumbfounded with how dressed up to be: Start with this outfit. Look great and fit in regardless of how dressed up the setting actually ends up being and ensure you have the confidence to put forward what really matters: Your awesome personality and expertise.

what to wear when not sure how dressed up to be

Thursday Boot chukka honey scout 210 east oak watch herringbone blazer target goodfellow Cashmere sweater amazon levis charcoal jeans

What to Wear When You’re Not Sure How Dressed Up to Be

Why this works:

Every item in this outfit is one that could be dressed up or down, and its chameleon-like properties come from its interaction with the other items.

This herringbone blazer from Target can easily be dressed up with slacks, a tie, and dress shoes. But because of its thick weight and texture, it’s also able to be dressed down. And if you show up somewhere and everyone is dressed more casually and you don’t want to be the one guy in a jacket, taking it off completely alters the dressiness of the outfit. Because we’re not wearing a collared shirt under the sweater, simply removing the blazer makes the outfit just a sweater, jeans, and boots. A perfectly acceptable casual outfit for any situation.

A thin cashmere sweater like this from Amazon’s house line could be worn dressed up with a suit and tie, or just with some jeans and sneakers.

Dark gray slim jeans, my personal favorite for versatility, can be dressed up due to their fit and color, but easily look modern and cool with a henley and a bomber jacket.

And perhaps the most versatile item in this Getup are the chukka boots. Lots of boot styles can be dressed up or down, but I find the chukka to be the most universal. I’ve had this pair from Thursday Boots for a couple years now, and are often my go-to when I’m just not quite sure how dressed up I should be. Their shape and thin sole allows them to appear more dressy, but the minimalist clean design also works perfectly with modern casual outfits like the henley and bomber.

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Herringbone blazer: Target, $50

Suede chukka boots: Thursday Boot Co., $149

Cashmere sweater: Amazon, $89

Gray denim: Levi's $41

Watch: 210 East Oak, $179

What do you wear when you're not sure how dressed up to be? Chat with me in the comments!

Andrew is the founder and editor of Primer. He's a graduate of American University and currently lives in Los Angeles. Read more about Primer on our About page. On Instagram: @andrewsnavely and @primermagazine.

  • Zac Silk

    This is a normal getup for me. I usually sub in a navy blazer and grey slim chinos. Having said that though I’ve stocked up on grey slim jeans this year.

    As well as that splurging on a cashmere sweater has been a worthwhile investment.

    My goal in my wardrobe is to have a cameleon wardrobe, and with suede chukkas are a perfect accompaniment for the other items.

    This seems like a perfect getup for a typical day at college for me and I’m going to find a herringbone blazer when I next can.

    • http://www.primermagazine.com/ Andrew

      That’s great! That would be a great look too.

  • rogun

    Great piece Andrew!

    • http://www.primermagazine.com/ Andrew

      Thanks! 🙂

  • Chris Romano

    Thanks Andrew, great informative article, and I learned a few things that I’m going to start doing right away..

    • http://www.primermagazine.com/ Andrew

      You’re welcome! What did you find the most helpful?

  • http://mfglimpse.blogspot.hk/ richie cheung

    Nice post. Awesome styling.

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