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What to Wear to Make More Money

A few months back, I switched jobs within the same company. It was a lateral move. I’ve been using that move as an opportunity to re-focus on my career and soul-search on early retirement and other goals. The conclusion I’m coming to is to stay on-course (lucky for you fine readers ha ha!) towards early retirement in early 2020.

Although I have a great boss, great colleagues, decent pay and work environment, there’s a strong pull back to the idea of working on projects and endeavors of my own choosing. Simply put, I still yearn for work that isn’t tied to that compact little cubical.

For a brief spell with this change, I’d taken on the mind-set of a careerist. I bought a bunch of new work clothes and even got them tailored to fit well.

One bit of advice I can offer after almost 25 years in Corporate America is to put some effort into your appearance. It’s an investment that will pay off, particularly for careers where “executive presence” is vital to promotions and increased pay. Just look around your office. By and large, your leaders are smartly dressed, but not too flashy, and sporting clothes that fit well.

What Constitutes “Smartly Dressed” for a Corporate Guy?

There are a few easy things you can do to make sure your appearance is as kick-butt as your performance and actual results. My top five list includes:

1.) Make sure your shoes always appear like new.

This doesn’t mean you need to buy new shoes all the time. On the contrary, buy quality leather shoes that you maintain with care. The number one absolute “must” is to invest in a pair of shoe trees for each pair of dress shoes you own. Shoe trees not only preserve the form of the shoe, they keep the inside of the shoe dry, slowing the breakdown of the materials.

Secondly, take the time to clean and polish your shoes at least once every six months. This alone makes your shoes look a lot newer, especially after sloshing around in snow and salt-treated sidewalks. Finally, stick with cordovan (or dark brown) and black as your shoe colors of choice. The light brown/caramel color is fine for casual Friday.

President Obama is always a good example to follow. Photo courtesy of Muhammad Ghafari

2.) Make sure your belt matches your shoes.

And make sure your socks match your slacks. You can get away with some fun patterns with socks, and I have a few fun pair I throw in from time to time. Just don’t go nuts here. Also, limit the jewelry to a nice watch (band that matches the belt, or stainless) and wedding ring, if you’re hitched.

3.) High-water pants are still not cool.

I roll my eyes in the halls when I pass by a colleague (usually a younger millennial), marching along with a nice suit, well put-together; but you can’t help but notice his pant legs flapping like 3T dungarees on a five year old. Make sure the bottom of your pant legs just touch the tongue of your shoes when standing up straight. We won’t get ’em wet when that big flood hits. Promise.

4.) Don’t be a Dwight Schrute with dress shirt colors.

There’s a few colors that always work with professionals: white and light blue. A few colors that work most of the time include light violet and ecru (which I think is a very light cream color.) Avoid the bright primary color dress shirts, that never look good with a tie (red, dark blue, dark green.)

If you have a few of the more neutral, darker color shirts (black, gray, or navy), keep them open collar, and wear with a sport coat on casual Friday. Sorry, Dwight, no brown shirts allowed. And please, keep ’em long-sleeved!

5.) Tailoring isn’t just for new suits.

Very few of us can get by without caring about what we look like, or what we wear. But for the rest of us, we gotta make sure our clothes FIT. Most suits aren’t tailored close enough to your form out of the store, unless you’re dropping serious coin on some serious threads (which I don’t recommend – this is a financial intelligence blog, remember…)

Make sure you find a quality tailor and instruct them to form-fit your suit. And then, do the same for your dress shirts. Most shirts, even the ones labeled “Athletic Fit”, leave a loose bunch of fabric around your waist (and arms too.) It shouldn’t cost more than $20 – $25 per shirt at a respectable tailoring shop.

6.) A bonus tip:

To save time on ironing during the colder months, throw a v-neck sweater over your shirt and tie. This is the only reason to want winter to last a little bit longer. No one, least of all me, likes to spend time ironing. Oh, just make sure those sweaters are form-fitting too!

Credit for this post goes to John T. Molloy, author of “New Dress for Success.” I picked up this book way back when I first started out in the corporate world, and it’s a reference that’s served me well over the years. I highly recommend picking up a copy. There’s a lot of other good advice that covers things like grooming, coats, and nick-knack stuff like tie-clips and collar stays.

Funny this duality I’m serving up to you here: professional dress advice from someone with a strong urge to burn his ties in an early retirement celebration. Yep, I’d rather be working on house projects; wearing beat-up jeans and paint stained tee shirts.

There’s a time and a place for everything. A modern gent should be ready to show up presentable, when the occasion calls for it. After that, you can take a match to the kit.

Dress Code for Success

Comments 4

  1. I was always told to “dress for the job you WANT, not the job you have”. I believe it is always better to be over-dressed than under-dressed. To be successful you must look successful.

  2. Good points but one additional one is a fit body in a rack suit will look better than a couch potato body in tailored duds. I am a runner and an early retired executive. I bought very affordable $200-300 suits off the rack and was constantly ribbed by my coworkers of wearing $3,000 suits. It wasn’t the suit but the fact that I wasn’t caring as much weight on my frame that made the suits look expensive. I’m not body shaming anyone, but as unfair as it may be, like you point out, looks matter. And if you are a person who can easily control your body fat, I know many can’t, then it will be one more advantage in the corporate world to do so.

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