Stories From The Hill

A behind the scenes look into image consulting and personal branding. Hill Image will get you there.
18 Jan 2017

Help, my son’s appearance would leave one assuming he’s lazy, apathetic and lacking confidence.

I am often asked if I work with men/ young men on their wardrobe.  I do.  I offer males the same one-on-one services that I do females.  Last April I stepped it up a notch and actually started selling a custom tailored menswear line, J.Hilburn, because there are such limited options for great fit in this area.  Especially for my extended size clients.  (The difference is amazing!!)

Notice how sloping his shoulders look in the blue shirt and how much “shirt fat”/extra fabric drapes on the blue shirt. The lavender shirt fits him perfectly and still allows him to move comfortably. (J.hilburn on right)

Yes, this is the same man. Notice that by perfecting the fit (we need to shorten the sleeves on his next shirt) he looks like he has lost weight!

With a more mature crowd, wives cringe over pleats and cuffs.  With the fresh out of college folk, parents ask “How do you get young adults over the ‘hump’ of realizing that their appearance is not a matter of vanity, but of professionalism?”  This can be tricky.

Here is one suggestion:

  • Assign him the task of researching (stalking) the employees of some of the companies he’d like to work for.  Physically drive to some of the locations.  When they get out of work, what are they wearing?  What does their hair look like?  Do they take care of their coats/outerwear?  What type of satchel are they carrying?
  • Research the city/area the jobs are located in.  What do the people look like there?  What are their hobbies?
  • Have him create an image board of what his life will look like/ what HE will look like if he works for these companies.
  • Determine and write down the adjectives would he want others to use when describing him.

I understand this may seem hilarious to suggest to a teenager or young 20 something.  If the vision board is just too quirky coming from mom and dad, figure out a way to rope his friends in on it.  Assign the task to all of them.  Hell, tell them you need them to do it for a colleague (me) who is doing research and have them email me the information!

If that’s not your style and you want to address it more indirectly, below are a few concepts you will need to address through items you purchase for your son (Macy’s, Men’s Warehouse, Von Maur, Goodwill):

  • Fit is More important than any other detail.
    • Hem pants (little to no break in pants these days) and Jacket sleeves (1/4″ of shirt should peak out from under jacket sleeves)
    • Jackets and sweaters are not life jackets.  Buy one that fits his body perfectly.
    • Have a tailor perfect the fit of his button down shirt to eliminate “shirt fat”
  • Style speaks louder than words.
    • No more baggy.  Everything is slim cut!
    • “Dress for the position you want”– just say no to t-shirts guys.
  • Hair is your most dominant accessory.  Groom it (all of it).
    • Clean and trimmed hair is essential.
    • Beards, stashes, brows, etc– groomed.  Lunch interviews are brutal enough without “saving some for later”
  • Shoes are more than a statement and a necessity.
    • Polish them
    • They’re the daily horoscope for your sign (after your hair).  You can tell a lot about a person by their shoes.
  • Posture, a smile, and a handshake sell you.
    • You don’t need me to tell you this.

Seat fits and does not droop at crotch. Pant is hemmed perfectly to hit the sole of his shoe. The leg width is relaxed but slim. (J.Hilburn)

Jacket is able to button but does not swallow him. The sleeves do not fall below his thumb knuckle (however, I’d shorten them 1/4″ more to show off a sleeve cuff). (Men’s Warehouse)

Pants on the left are too long. Pants on the right are hemmed perfectly and are a good quality pant that won’t show many wrinkles. (J.hilburn on right)


If you are interested in learning the key pieces to have in every gentleman’s wardrobe, email me at  I’ll gladly send you the checklist along with some great pointers if you provide some details about your son.

Good luck!  You got this!


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