3 Rules for Dressing to Impress (in the workplace)

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I need to preface my post that these are going to be tips for men. Sorry ladies, don’t know enough about it to write a helpful post. Plus, who am I to comment on women’s fashion? 

Growing up with two parents who were in the shoe industry, I was constantly immersed in shoe and fashion trends. It started out as something my parents did; as I grew older, I took greater interest in their occupations. I saw shoe samples, prototypes, drawings, trade magazines all over the house at all times. It turned from our daily life into a lifelong interest and hobby; demonstrated by the sheer volume of what’s in my walk-in closet. Most people that come to see our house joke about how much room my wife “leaves” me in our closet. Truth is, I have just as much as she does. 

My goal with this post is to educate you on how to look good in professional settings and how to make a great killer first impression, because you can tell a lot about a person by the way they dress. 

1. Wear clothes that fit! 

My biggest pet peeve is seeing someone with ill fitting office clothes. It makes you look sloppy and not to be taken seriously. 

So here’s my most important tip of this post. Find a great tailor! When you find a great tailor, hold on to them and never let them go. It’s becoming a lost art in North America but so critical when it comes to looking well put together. Your tailor will be able to take any clothes you buy off the rack and look like they were made exactly for you. When you’ve made enough money, you should also pay a tailor for bespoke suits. 

You won’t be able to use your tailor for every piece in your closet so you need to know your measurements. Get measured by a tailor and take note of your neck, chest, sleeve length, waist, inseam. 

Pro tip * keep a tape measure around so you can measure yourself when shopping online * 

Knowing your measurements will give you confidence to shop at any store and buy the right size. 

Learn your measurements, find a tailor, and you are on your way to looking sharp for any occasion. 

A great place to get clothes that fit you is bonobos.com They offer multiple fits based on your body type – slim, tailored, straight, athletic. I can’t believe it took this long for a retailer to understand that men want clothes that fit and more sizes than S, M, L, XL. I’m not an affiliate for them, just love their selection and think they’re going to be a major player soon (if not already). If you live in a major city, see if they have a brick and mortar location. They measure you in-store and recommend fits and sizes. 

2. Have these Staples in your closet to Impress 

This will vary based on your career and your workplace culture. Working at a tech company like Wayfair, Google, or Facebook, you’ll probably get away with a business casual to casual look. If you work in finance or law you’ll be wearing a suit and tie regularly. 

Regardless, here are staples in your closet that will work universally. 

Dress shirts: Get 4-5 shirts to use in a regular rotation. I like to go with basic neutrals, blue, and black. Basics don’t go out of style and you’ll save money in the long run. Also I recommend 2 or 3 statement shirts with fun patterns that you can wear to a party or a date. Go with a tailored fit and don’t be that guy wearing a shirt that looks like a blouse. 

Dress pants: This will vary based on the climate you live in. If you live in Southern California you probably don’t need wool pants like I do here in the Northeast. I recommend having 3-4 pairs that you can use in a regular rotation with your dress shirts. Again, go with basic colors like black, gray, navy, and khaki. If you work in a business casual environment, go heavier on chinos and if you’re in a more formal setting go with more trousers. Again, I recommend going with a tailored fit to look professional. Also when trying them on, make sure they are comfortable to sit in. 

Polo shirts: If you run hot like me, you’ll need 3-4 of these bad boys for your summer rotation in basic colors and 2 or 3 statement pieces. 

Sweaters: Go with 2-3 sweaters in a rotation that are comfortable and can be worn by themselves or with a collared shirt underneath. Christmas sweaters need not apply. Banana Republic, J-Crew, Bonobos, Calvin Klein are some of my favorite retailers for sweaters that offer good quality but not kill you on prices. 

Suits: Every grown man should have 2-3 suits in their closet. If you are starting out your suit collection, go with black, navy, or gray. These colors are versatile and can be combined in multiple combinations with shirts, sweaters, even a nice t shirt for a weekend look. I prefer a single breasted 2 button jacket with no pleats in the pants. Calvin Klein offer a great modern styling but entry level pricing. If you have a little more cash to spend, I like Hugo Boss to offer sharp modern men’s styles. Check out their outlet locations for better pricing. 

If you attend regular formal events, it may be good to grab a black or blue tux as well. You can use the tux jacket in combination with a t shirt and nice jeans for a great casual look. 

Once you have your basic staples in your closet, I recommend getting a fun blazer that you can throw into the rotation to mix things up. 

Shoes: Have a pair of black and brown dress shoes that are comfortable and durable. Spend money on a better quality shoe and find a cobbler that you trust. This way you’ll have shoes that will last you years and give them character as they age. Do not buy shoes with a square or pointed toe. That was a trend that lasted a few years in the 2000’s and it didn’t end quickly enough. Who’s feet are shaped like that anyway? 

Stick with traditional styles like oxfords, loafers, chukkas that won’t go out of style. 

Also make sure you have a good pair of sneakers that can be worn in a business casual setting like an Adidas Stan Smith, Nike Air Max, New Balance 998. If you want to get fancy, go for a high end fashion brand like Gucci, Christian Louboutin, Louis Vuitton. 

Another company I like is Common Projects, which offer leather sneakers that are more expensive than your average sneaker brand but a better quality and not as expensive as luxury brands. 

Accessories: I’ve been getting into stepping up my accessories game the last couple years now that I have most necessary staples I need in my wardrobe. Here is what will set you apart from the crowd and get noticed. Especially if you pair great accessories with basic staples. So let’s get crazy here. 

Couple items that are worth spending money on – work bag, travel bag, and watch. I recently bought a Tumi work bag and absolutely love it. It’s great quality that has modern styling. I get compliments on it all the time. They also make sure that their pieces are practical. 

The weekender travel bag I use is from Hook and Albert. I love it because it’s also a garment bag that you can use to pack your suit without it getting too wrinkled from travel. 

Re: Watches – I’m really getting into the watch game lately, probably turning into a little big of an obsession. If you’re not looking to spend big money on a luxury time piece, I recommend looking into: Shinola, Daniel Wellington, MVMT for entry level time pieces. A step up from that would be Swiss watch companies like Tissot, Oris, Tudor. 

If you want to get into serious time pieces, I recommend getting a sports watch like the Rolex Submariner. Luxury sports watches look good with any outfit and will get positive attention. 

A great looking watch will complete a look like jewelry does for women. 

3. Importance of Self Care

Part of completing your look and being well put together is self care. 

Make sure you are on a regular fitness regimen. Find something that you enjoy doing so that you’re motivated to do it on a regular basis. Getting your blood flowing is good for mind, body, and spirit. You can find thousands of studies on the positive impact it has on mental health and mental clarity (not going to bother with physical benefits because that’s obvious). It helps you feel more confident and relaxed, which, will do wonders for your business and personal relationships. My preference is a combination of weights and cardio. I use those moments as a chance to refresh my mind and body. 

Personal hygiene – Use deodorant that’s not offensive and same goes for cologne. One or two sprays of cologne is all you need. There’s nothing worse than walking into an elevator with someone that put on an oppressive amount of cologne or perfume. We’ve all been there, don’t be that guy. 

Get regular haircuts from a master barber to keep you looking good. Don’t forget about keeping your nails short or trimming any excess nose or ear hair (for those of us in a certain age group). 

Keep your skin looking good by drinking plenty of water. My wife is a professional make up artist who specializes in Wedding makeup. Her number one tip to all of her brides is to drink water. It’s amazing what drinking enough water for a month will do for your skin. You’ll notice less fine lines, puffiness, and reduce dark circles under your eyes. Not to mention you’ll have more energy for your life. 


I hope this post helps  you. Let me know what you think by leaving a comment below.  

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