In our latest piece for ESM we discuss the transition from entry level to mid level dressing.  It's a transition.  We'll help you get there.

Last month we discussed dressing well even when you can’t afford much.

Dressing on a budget is important, but eventually you will graduate, you will get a promotion, you will get a raise and your budget will grow.

Many of the articles and websites on menswear talk about shopping on a budget, or about acquiring aspirational pieces that most men will never be able to afford.

The men in the middle are the ones left out.

This month we discuss those middle men. The men making more than a little money but less than a lot who want an end to look good. They are transitioning from entry level to mid-level in their career and their wardrobe needs to keep up.

Have a seat and take a listen.

Suits for the Middle Manager

  • Two suits are essential but five suits are better. Wool is great but fabric mixtures are the next level.
  • Buy suits with two buttons or three buttons that roll down to two, peak lapels, with one or two vents. Add a double breasted to the rotation. Keep it classic.
  • Solids and pinstripes are foundational. Try patterns like herringbone, Glen plaid, houndstooth and windowpane. Gray and blue are classics. Mix it up with colored pinstripes and speckled solids outside and colorful linings inside.
  • Step it up with a bold chalk stripe. No reason to blend in with all the other candy stripers.
  • Upgrading to five suits will provide a healthy rotation. Just like shoes your suits need a rest and adding more options will make any man feel his best.

The good news? You don’t need to spend more than $1000 to get a good starting line-up.

Shirts and Ties

Seven dress shirts get you through the week. Twelve to fifteen will give a man a handful of proper choices. Ten for two weeks of work, and three to five for a couple weekends.

  • A professional man should keep a crisp folded shirt in his car in case he needs a change headed to happy hour or an afterhour’s affair.
  • Solids and stripes in white and blue are nice. Solids and stripes with contrast collars and/or cuffs are better. Flirt with different collar styles. Add a cutaway and/or a club collar.
  • 100% silk ties are the standard. Look for mixtures in silk/wool, linen/silk, or cashmere/wool. Add a few with texture and/or pattern. A crest tie is good way to show your personality.
  • The four-in-hand is the king of tie knots but it won’t hold up well under a cutaway. Try a double four- in-hand or even a half Windsor which will give you a beefier knot with more heft.
  • Instead of going for slim and trim like the cubicle guy try a tie in a wider width to go with your wider suit lapels and you’ll gain a new level of respect from your subordinates and peers.

Trousers and Belts

Three pairs of trousers of will get you through. Five to seven pairs will get you noticed.

  • Add flannels, cottons, and gabardines in checks, stripes and plaids.
  • You may choose pleats or no pleats depending on your body type and personal taste, but be sure they are meticulously tailored and fit you well
  • Two belts are sufficient. Five belts are sublime.
  • Make them high quality leather, suede, or alligator with sleek buckles that do not draw attention to the waist.
  • To be sure the leather is quality look for the 100% leather or alligator stamp
  • There should be no creases in the leather and it should reform to its original shape after bending

Dress Shoes

Men who are upgrading their wardrobe will invest their money in quality shoes.

  • Two pairs won’t get it done; five to seven are a must.
  • Look for high quality 100% calfskin or suede in Goodyear construction. If cared for properly these will last longer than you.
  • Add shoes with thin soles for the city and thick double soles for the country.
  • Choose a wingtip, whole cut, perforated cap toe, or slit toe blucher and keep them shined and/or brushed.
  • Use shoe trees. They will keep the shape of your shoe and keep your shoes from smelling like, well, your feet.

Underwear and Socks

Actually, more like undershirts. Again, you need at least seven. One for every day of the week.

  • Buy gray. Gray actually looks better under white shirts (as in you can’t even see it) and no one will be able to tell.
  • Skip the plain socks and go with color, pattern and texture. Add stripes, checks, and dots. Look for wool, silk, Egyptian cotton and cashmere. Try colors like purple, bright blue, fire engine red, and yellow.
  • Only buy over-the-calf hosiery as the bare leg should never be seen when a man crosses his legs.


This is the extra ten percent. Where most men blend in, a select few stand out. You should be one of the few.

  • A good watch is a must. Stylish men should have three watches. One for work, one for formal attire, and the other for sport.
  • Pocket squares are essential. A good suit is nothing without the proper finishing touch. Look for linen, silk, or cotton.
  • Tie pins, collar bars, cuff links, lapel pins, boutonnières, are all in play. Just don’t wear them all at once. The subtle statement is the best statement.

Transitioning from entry level to mid-level doesn’t need to be difficult but just adding to your wardrobe isn’t good enough.

Numbers without results are nothing. If you’re going to double the size of your wardrobe make sure it’s with quality items that will last you until your next wardrobe upgrade.

Don’t worry, we’ll get to that later.