Home / Career Development / Dressing to Impress: 4 Essentials to Look Like a Boss
Dressing to Impress: 4 Essentials to Look Like a Boss

Dressing to Impress: 4 Essentials to Look Like a Boss

Cham­pi­oned by: Daniel Stock­ton
Co-Authored by: Nevin

From ‘Frat’ to For­tune 500

Do you want to learn why dress­ing to impress is impor­tant? Of course you do…

Let me tell you two things I already know about you:

1. You own a pair of Sperrys

2. You’ve worn said Sper­rys with khaki chinos/button up, and con­sid­ered it “busi­ness casual”

If I’m wrong, I’m wrong — but I’m not.  Today we cover a few basic ten­ants of dress­ing to impress.  Most of us, whether it’s in col­lege or fresh out, are dress­ing up for intern­ships, inter­views, and brand new 34k-a-year big-boy jobs.  Regard­less of your rea­son, your game-plan should remain the same.

The prob­lem?  Most of the time, nobody cares to tell us the off-the-rack Polo blazer we bought at Stein Mart looks like a hand-me-down from Grandpa Bill.  You know what I’m talk­ing about, cuffs too long (we don’t know where they should break), shoul­ders too wide (but we’ve been in the gym, and we’re def­i­nitely a 44 reg­u­lar), vent still sewn shut (they never sewed my trendy Amer­i­can Eagle jacket like that).  Noth­ing worse than see­ing a sharp guy in a not-sharp sport-coat.

[Sighs, sips scotch] Here’s what we need in order for the boss to com­pli­ment the tie*:

1. Rub­ber is for pro­phy­lac­tics, not dress shoes

Unless you live in a trop­i­cal rain-forest where it rains 70% of the time (Seat­tle, but even then… no), you should never put on a suit and a pair of dress-shoes with rub­ber soles (see my approved busi­ness casual rub­ber shoe, Sper­rys and New­Bal­ance not included).

Leather soles, my friends, and only leather soles.  I don’t need to explain, but I will. Leather soles make noise, and that noise announces you as you make your way down the hall, it dis­tin­guishes you — and solid­i­fies your pres­ence.  It’s all about how that sound makes you feel, and it makes you feel good!

2. Tai­lored suits are not an option, they are mandatory

Why spend $500 (in our case, as young pro­fes­sion­als) on a piece of cloth­ing that doesn’t fit you per­fectly?  Why spend $500 on any­thing, any­where, that doesn’t do every­thing it’s sup­posed to do… per­fectly?!  Check out these up-and-coming hab­er­dash­eries  that make custom-fitting suits a breeze. Here’s another trick — either spend the money to get the suit tai­lored, or nego­ti­ate the tai­lor­ing into the price.  Prime exam­ple:  Jos. A. Bank runs more sales than the dol­lar gen­eral store (think about it…). They are always wheel­ing and deal­ing, so wheel and deal back. Tell them you’ll buy the three suits you’re try­ing on, but you want the alter­ations included in the total price, and a shirt and tie to boot.  Most of the time, they’ll work with you on a deal.**

Couple resized 300x300 Dressing to Impress: 4 Essentials to Look Like a Boss

And remem­ber this… a well-tailored suit is to women what lin­gerie is to men.

3. Ditch the clas­sic fit para­chute shirt, it does you no favors

Parachute Resize 300x200 Dressing to Impress: 4 Essentials to Look Like a Boss

You know what I’m talk­ing about, pal. I won’t explain, but visit my guy Charles Tyr­whitt  and sign up for the monthly cat­a­log — their sales are insane and their shirts are the best bang for your buck.  Wel­come to the world of cus­tom fit dress shirts, sir.

4. Acces­sorize with ties 

Power Tie Resize 300x224 Dressing to Impress: 4 Essentials to Look Like a Boss

We’re going all out with the tie. We want this bad boy to pop; we want our tie to DEFINE power. Not nec­es­sar­ily with a crazy pat­tern, but a promi­nent color that will stand out. Remem­ber, we’re look­ing for an atten­tion grab­ber to turn heads, how­ever we don’t want it to be too loud, and the only thing they can look at (i.e. — fig­u­ra­tively smacks them in the face, not a crush­ing blow leav­ing them down for the count). It’s sup­posed to catch their eye and then draw atten­tion to the “Money-Maker” (your dev­il­ishly hand­some face).

That’s it.  Four steps, each with its own respec­tive action item. How­ever, we warn you: once you start look­ing damn good, you can never go back.

Over the next few weeks we will delve fur­ther with sev­eral of the subtopics listed above, mak­ing sure you have this look­ing good thing down pat. Be on the lookout!


* If some­one com­pli­ments your tie, they are com­pli­ment­ing your look.  They’ve sized you up, and like what they see, but don’t want to give it all away.  So, they com­pli­ment the tie.  “I like your tie” will usu­ally mean, “hey, you’re a good look­ing son-0f-a-gun”.  Unless, of course, you’re not look­ing good, in which case — it’s just the tie.   
**NO PLEATS.  Are you under the age of 40 and still in good-enough shape that you don’t mind hav­ing the lights on when you… for­get it.  No pleats.  Pleats are to make fat peo­ple look less fat.  You’re bet­ter than that.


Have any ques­tions or fash­ion tips for us? We would love to see them in the com­ments below!


  1. I like the arti­cle, I only wear cus­tom and made-to-measure suits…Astor and Black and J Hilburn. Noth­ing bet­ter than a per­fectly fit­ted suit of fine con­struc­tion and impec­ca­ble tex­tiles. The only thing bet­ter than look­ing like a boss…is actu­ally being the boss.

  2. Great arti­cle, loved it. Only ques­tion I have is, when is it accept­able to wear a now tie?

    • Bow* tie

    • Bet­ter ques­tion, when is NOT accept­able to wear a bow-tie? Ha! Only kid­ding. I do love a good bow-tie. My advice is this, at for­mal events (wed­dings, com­pany din­ner, etc), they’re always accept­able — I’d say almost uni­ver­sally. For daily wear, it’s at your dis­cre­tion. I know a few classy guys that wear noth­ing but bow-ties, and that’s their “thing”. But if you’re young and work­ing your way into the com­pany, maybe you’re not sure if your boss approves of them or not, just give it a shot an gauge the feed­back. If you just need an excuse to rock a solid bow-tie you picked up on sale, just call it Bow-Tie Thurs­day (that’s what we do!).

  3. Hilar­i­ous and help­ful arti­cle! I’ve been on the Charles Tyr­whitt site for a good 20 min­utes now, some great stuff. For ties, what kind of knots should I be wear­ing? I would love some advice.

    • Tan­ner — highly rec­om­mend you per­fect two knots. Wed­dings, events, galas, etc, rock a half-wondsor. And for daily work/leisure/just to look awe­some, per­fect the four-in-hand (work­ing man’s knot).

      The key to either is a solid dim­ple. Ties are like dogs, they can be trained. Tie it right from the begin­ning and it will even­tu­ally just fall into place!

      Good luck, sir.

Leave a Reply

Your email address will not be published. Required fields are marked *


Scroll To Top