The Complete Guide to Dressing Like a Top Performer (for Guys)

The difference between looking like a chump and looking like you have a sense of style can be the difference between being perceived as a mover and shaker or a guy who has hit his ceiling in the workplace. Like it or not, humans are naturally judgmental beings and we make snap judgments about people within the first 10-20 seconds of seeing them. How you dress affects how you’re perceived by both current and potential employers, colleagues, and even new friends or potential significant others.

If you’re looking for a raise or promotion, a new job, or its time to start settling down and looking for a spouse, one of the easiest ways to start cleaning up your image is to give yourself a wardrobe makeover. It doesn’t have to be hard and it can be an impactful move for your career.

We’ll cover casual, business casual, and professional attire, as well as a few grooming tips to get you off to a fast start.

Make Casual Look Good

Casual dress will rarely mean that it’s time to run to the closet for sandals and shorts. In fact it’s highly unlikely that you’ll be asked to wear ‘casual dress’ in most business settings, but there are a couple of instances where it is possible:

1. If the company culture is truly laid back and their style is ALWAYS casual. This would be a unique situation in which the interviewer would explicitly say: “Please do not wear anything more formal than jeans and a polo,” or something similar.
2. If you’re headed to a casual social gathering at a sports game or some other team building activity
3. If you head out with friends or decide to attend a young professional networking event

When it comes time to look into the closet and figure out what the heck to wear, you need to know what you’re doing. First, follow the directions from your invite or contact. In the second point above, you would wear jeans and a polo shirt. If the invite or contact simply states “casual dress”, then stick to these guidelines:

1. Wear a pair of khakis. Dress khakis are best, but a nice pair of pressed khakis will be fine.
2. Wear a decent polo shirt, golf shirt, or a casual button down. If the weather is cold, consider a sweater as well.
3. Wear a leather belt.
4. Always wear shoes that match the color of your belt. Brown is usually a good color for a casual setting.
5. Wear socks. Even in a casual setting. Your socks should always match the color of your pants. If you don’t have khaki dress socks, then wear a pair of blue dress socks.
6. Jewelry for guys should be kept to a watch. Don’t wear a running watch, and don’t wear a MontBlanc or Rolex. Something simple like this or even this will be just fine. A leather-band watch is a great choice for casual attire. If you go with the leather band option, the band should match the color of your shoes and belt.

Remember – there will always be exceptions to these guidelines. If you’re interviewing at Facebook, I would highly recommend NOT wearing khakis and loafers. Facebook isn’t the only laid back workplace around town these days either, so it all goes back to doing the right research and knowing your stuff. Before you ever apply for a job, you should know about the culture and work environment — otherwise it means you’re just taking shots in the dark and applying for jobs online, but that’s a post for another day.

Business Casual: The Business Standard

Business casual dress is the norm for pre-interview dinners in most settings. In some instances you may be explicitly told to wear business casual to an interview as well. Use your best judgment, but here are some basic guidelines to go by:

1. Wear a nice sports coat or blazer. They should have two buttons and fit you well. You should have two sports coats in your closet to start off: one black and one blue.They should be two-buttoned and single-breasted. Here’s a great example from the Jos. A Bank site.
2. Wear a basic shirt. Solid colors are best. White, light blue, and light yellow are your best options. A subtle, patterned shirt is also acceptable.
3. Wear dress slacks. Dark gray or dark khaki are best. You can wear both colors with both jackets. If you are in question about how to combine the pants, shirt and jacket for a cohesive outfit, call me or go to your local Jos. A Bank and ask for advice.
4. Wear a pair of nice dress shoes. Black is usually best. You can wear dark brown if you are wearing the blue blazer. I always wear pinch tassle loafers, but many career sites lean toward laced dress shoes. I personally feel this is a matter of style and either one will do. I wear Cole Haan dress shoes because they are high quality, last forever, very comfortable, and scream professionalism. If you’re on a budget, check out your local Payless or other shoe outlet for similar styles.
5. Match your belt to your shoes. This is very important — nothing screams ‘bozo’ like a black belt and dark brown shoes. If your shoes are mahogany, your belt should be mahogany. If your shoes are black, your belt should be black.
6. Match your socks to your pants. Dark grey pants with dark grey socks shows thoughtfulness and professionalism. Dark khaki pants with dark khaki socks shows you thought ahead. If all else fails, match your socks to your blazer.
7. A tie is optional for business casual. If you are interviewing in business casual, wear a tie. If you are going to a pre-interview dinner, then the tie is truly optional. Stick to subtle patterns like stripes and small dots. When in doubt, ask an associate at Jos. A Bank or email me with a picture of the tie.
8. Jewelry for guys should be kept to a watch. Don’t wear a running watch, and don’t wear a MontBlanc or Rolex. Something simple like this or even this will be just fine. (I wear a Fossil.) If you choose to go with a leather-band watch, the band should match the color of your shoes and belt.
9. Earrings and other jewelry should be removed and tattoos should be covered.

I’ll leave you with the same caveat for business casual as I left in the casual section of the post. KNOW THE CULTURE. Period. you’re going to get sick of me saying that throughout our business and career guides… but guess what? I say it for a reason.

Professional: Look Like a Stud

Professional attire will likely be the dress code for your actual interview. Professional attire means suit and tie for guys. Here are the some guidelines to follow:

1. Wear a suit that looks good, isn’t too flashy, and fits well. Dark blue or dark grey are the typical recommendations for suit color. I stand by those recommendations. If you are starting from scratch on your wardrobe, tell the Jos. A Bank associate you want two suits, one in each color. You want to have them tailored to fit you as much as possible. I go with cuffed, pleated pants with a medium break. Style guides go more for a flat front, no cuff, and medium break look. The style is up to you. ** According to Askmen.com, “the break is where your pants fall on your shoes, creating a horizontal crease in the fabric across the front of your pant leg.”
2. Wear a basic shirt. Solid colors are best. White, light blue, and light yellow are your best options. A subtle, patterned shirt is also acceptable.
3. Professional dress means a tie is required. Once you’ve landed the job, wearing a tie is a chance to express your personality (if you have to wear one at all). But, in an interview, a tie should not be a distraction and you should not make a statement with it. Stick to subtle patterns like stripes and small dots. When in doubt, ask an associate at Jos. A Bank or email me with a picture of the tie.
4. Wear a pair of nice dress shoes. Black is usually best. You can wear dark brown if you are wearing the dark blue suit. Again, I always wear pinch tassle loafers, but many career sites lean toward laced dress shoes.
5. Match your belt to your shoes. If your shoes are black, your belt should be black.
6. Match your socks to your suit color. If all else fails, where black socks with black shoes, and dark blue socks with brown shoes.
7. Jewelry for guys should be kept to a watch. Don’t wear a running watch, and don’t wear a MontBlanc or Rolex. You never want to wear something that will show up the interviewer.
8. Earrings and other jewelry should be removed and tattoos should be covered.

Get Cleaned Up

First things first, get a haircut. If you’re like me, then you’re very particular about how you like your hair to look.

• Option 1: Get your haircut the day before your interview if you have a barber or salon that you trust. Make sure they clean up the side burns and neck line. It’s best to have your hair cut above your eyebrows in the front and above the ears on the sides.
• Option 2: Get your haircut one week before the interview if you don’t have a regular barber or salon. If they screw up, it will give your hair a week to look more natural. Go back to the barber or salon the day before and have them trim ONLY your sideburns and neckline.

Cut your nails the day before the interview as well. Yes, I’m serious. No one wants to look at long, nasty nails throughout an entire interview. If you don’t have nail clippers, go buy some from the store.

The day of your interview:

• Get a good night’s rest the night before.
• Get up early, do some pushups and situps to get your energy level up
• Take a shower
• SHAVE with a razor that gives you a close shave. If you insist on maintaining your facial hair, I’ll leave it up to you to figure out what looks professional. At the very least, trim it up to a consistent length. If you don’t have a FULL beard, I would lose it — after all a half-baked beard is not something to be excessively proud of.
• Don’t forget your deodorant, but don’t put on cologne. The last thing you want is for your interviewer to despise the smell  of your cologne. Or even worse, for you to have the misfortune of wearing the same scent of an ex-boyfriend. Just leave the stuff on your dresser today.

Bonus: How to Know What to Wear to an interview

Option 1: Look at the interview invite email. If you’re interviewing for a job that we recommended you for through the Living for Monday Talent Pool, we’ll be very explicit about the dress code for your interview. Anyone working to fill entry-level jobs should provide the same kind of clarity. Before you move on to any other steps, be sure you check your interview invite for any reference to appropriate dress.

Option 2: If you have a friend who interviewed with the same company (or maybe even for the same position), ask them a few questions. Was there a pre-interview dinner? What did the company employees wear to the dinner? What did your friend wear to the dinner? What did the interviewer wear to the interview? What did your friend wear to the interview? Did they feel over-dressed, under-dressed, or just right?

Regardless of what your friend says, use option three below. (As long as you first checked the interview invite)

Option 3: Contact the person that invited you to interview. Calling them is the best option. If you don’t have their number, don’t feel comfortable calling, or catch them at a bad time to talk, then use email instead.

Say something like this:

Dear [name],

I hope you are doing very well!

I am looking forward to my interview on [date]. I checked the interview invite and did not see any reference to dress code for the pre-interview dinner and interview.

Company culture is one of the most important aspects of my job search, so I want to be sure to match [company name]’s culture with my dress. Would you please confirm the typical attire for the pre-interview dinner and the interview itself?

Thank you for your time.

All the best,

[Your Name]

[Note: Not all companies will host pre-interview dinners, but I want you to be prepared for anything.]

Now that you’re armed with surefire information about the dress code for the pre-interview dinner, it’s time to pick out your outfit. You’ll have three possible styles of dress to choose from: casual, business casual, and professional. This is your no-BS guide to all three.

Sum it All Up

Once you’ve interacted with a particular employer a couple of times, you should have all of the information you need about what you should wear. Pay attention to those around you. How do the high performers dress? Take cues from the people who have the jobs you want to fill some day and make it a point to dress in a similar manner.

So much of landing a job that will make you fulfilled and maximize your impact on the world is about knowing the culture and using your intuition. Trust your gut, and if you end up in a situation where you’re dressing in a way that doesn’t fit who you are and what you want… It might be time to reconsider whether you’re even interviewing for a job that will allow you to thrive.

What questions do you have about attire for interviews and networking opportunities with potential employers? Let us know in the comments and we’ll bop back in to give you the best answers we can come up with!

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