Dress Like A Boss!

Are you a young Professional man? Did you just land a new job?

That’s awesome! Congratulations! Now that you have landed the gig it’s time to start considering your wardrobe! Whether this is your first real job, a switch from a more casual office or just a fresh start it’s a great time to refresh your work wardrobe!

I know that this sounds scary and expensive! But it doesn’t have to be – if you have a strategy it can be simple and inexpensive to build an awesome work wardrobe!

Now let’s jump into it!


Always look sharp with a suit!

I know – you may work in a business casual office where you won’t wear a full suit often. But I want to challenge you to play the long game. Don’t be the guy who wears the same tired suit to every wedding, funeral and interview! Be an adult and pick up a few suits! This way you will be prepared for a big meeting or last minute interview opportunities! Plus – it never hurts to mix in the suit every once in awhile to keep people guessing. Additionally, as part of our strategy you will be able to wear the suit pants as part of your rotation.

When you are starting out don’t pick bold patterns or colors. If that is your taste, fine, mix them in later when you have a larger collection. True problem with bold patterns is that you cannot wear them frequently and they can be tricky to wear with complementary clothes.

Stick to the solid classics! I recommend the following;

Charcoal Suit
Every man needs a nice Navy suit

Dress Pants

I recommend that guys pick up 3–5 dress pants or slacks. These will be your workhorses – with suit pants occasionally mixed in.

A few guidelines to keep you looking good:
* Keep it classic – nothing that will standout!
* No pleats – these make you look wide
* Avoid Black – black pants fade quicker and show more lint etc. avoid if you can.

All that negative out of the way! I recommend you pick up the following:

  • Navy
  • Brown or Khaki for casual Friday’s only!
  • Dark charcoal
Ministry of Supply
  • Lighter Charcoal
  • Gray

Coats and Outwear

Depending on where you live this section may vary in importance! I happen to live in the Northeast so this is an important section for me.
Consider spending on a quality coat – it will last longer and you are seen in a coat much of the year.

I find it best to think of coats in terms of season:

  • Fall/Spring
    • Trench: if you wear a suit this is a must. Keep dry and look professional!
Prada Trench
    • Wax Jacket: for a more casual look that works well on weekends too!
Barbour Basic jacket – perfect for transitional periods of the year
    • Fleece: keep a nice fleece in the office for unexpected cooler days.
Patagonia Fleece is perfect for the office
  • Winter
    • Wool Coat: this is your workhorse! It helps to have a couple to extend the life. I prefer longer charcoal wool coats to the more casual pea coat.
    • Winter Jacket: not really part of your work wardrobe but consider getting a decent looking one if you live in an area where snow and wind make even a wool coat useless against the weather. You don’t want to be the guy wearing a loud ski jacket to work!

Dress Shirts

Finally, if you want to show your personality this is a place you can start! I am more conservative so I keep it pretty classic. The key here is fit, quality and finishings.

Check out this guide on how a shirt should fit! If you find a maker and cut that works for you – keep buying that style shirt! Don’t over think it! For finishings just be careful to buy the collar and cuffs that you want – don’t buy a French cuff if you don’t wear cuff links!

In terms of what to buy I would recommend a mix like the one shown below!

  • 3 white
    • 2 light blue
    • 4 conservative patterns
    • 1 wildcard (pink or yellow)


    If you have the misfortune of having to wear a tie every day I suggest you check out these guys, The Tie Bar for help building a collection. To start – I recommend keeping it simple. That means lots of solid, pin dot and stripes ties! Save the novelty ties for Christmas parties.

    Sport Coat

    Pick up a Navy Sportcoat to elevate a more casual outfit as needed! I always have a sport coat on the back of my door!


    The first thing a woman will notice on you is your shoes! Don’t leave the wrong impression – spend money on your shoes and take care of them!

    If you are just starting out pick out the best of these that you can afford – look for Goodyear Welting and leather soles.

    Black Oxford

    Loake Rothschild

    Brown Oxford

    Loake Shoes from England


    Crockett and Jones

    Add duplicates as your budget grows – this will help you rotate your shoes and extend their life!


    Don’t overlook your accessories! Again I prefer to fit in with my dress so I keep my accessories understated!

    • Socks

    I like to ensure I have fresh socks so I subscribe to Brummell for premium socks.

    • Scarf: a nice scarf will truly elevate your winter look.

    PS: if you purchase any of these great products through my link I may, in some cases, make a small commission at no additional cost to you. We appreciate your support.