Dressing Like A Man: Starting Out

I’ve gotten a lot of requests for this post, so I’ve done my best to try and frame the story.  The transition of a college student into the real world is hard enough, and that quick realization that your wardrobe needs to completely change is another dousing of cold water.

I get it.  Your college wardrobe was easy, especially in the last couple years  when you really had your legs under you.  Beat up jeans, old sport shirts, t-shirts, and some form of ‘loafers’, topped off by some ironically funny hat…

Then you have your first week on the job.  With a couple lunches at non-wing places.  And your first night out at an adult bar as a post-grad.  Eesh…it becomes glaringly obvious that you need to update your wardrobe.  It’s time to grow up.

The purpose of this post is not to rag on the past, but to give directions on how to move forward.  It can be intimidating and expensive.  But there is a way to do it and, with some shortcuts, you’ll be in a good spot.  It’ll take time to get you where you feel completely comfortable, but commit to the process and it’ll pay dividends.

The first thing you need to do is get professionally measured.  Go to any mens store and they’ll do it for you.  Tell them that you are getting started out, and you want to get measured.  Smart mens stores will be happy to do it for you, assuming that you’ll be a future customer.  It’s important to get these measurements because moving forward, you should only buy clothes that fit.  Nothing too baggy or (worse) too slim.  Baggy clothes make you look 20 lbs heavier than you are, and skinny clothes look like you shop at Structure.

Once you have your measurements, it’s time to get shopping.  Even if you work in a ‘casual’ environment, dress up.  I’m not saying that you should wear a suit, but dress for the job you want, not the job you have.  Focus on quality fabrics and fit, and work on building a wardrobe, not buying one in a single day.  Let’s break it out:

Shirts:  Plenty of options here.  Focus on 100% cotton shirts (or minimal stretch).  I’m not a huge fan of non-iron shirts because they get dingy and feel like plastic.  They don’t have as long of a life span as must-iron shirts.

You need two good dress shirts to wear with a tie.  Getting a couple bespoke shirts may be out of the question, so start off with a couple solid options from Banana Republic.  The cut is good, and they are always on sale.  Just don’t deviate too far from the mean.  Stay with blue or white solids.  Maybe a blue stripe.

As for everyday shirts, Brooks Brothers Red Fleece makes some nice must-iron solid oxfords for a really good price (and they are always on sale).  Grab a few of the solids and a couple plaids and you are in business.

Secondhand Options: (I’m going to talk about buying second hand for the majority of the categories.  If you aren’t into it, then skip to the next section).  For shirts, there are TONS of options at Goodwill, and you can find some really great deals for ~$6/shirt.  With shirts, remember that fit is key, and that trumps any special brand you find.  Again, look for 100% cotton options and make sure the fit is where you like it.  Try it on.  If it’s a little wide or the sleeves are too long, take them to your tailor and have it altered.  A $6 shirt with $20 worth of alterations is a good deal.

Pants:  There are a TON of options for pants, but I’m going to focus on the middle 80%.  To get started, I would get a couple pairs of chinos – tan, navy, and grey options in something that fits well.  Duck Head Gold Schools are nice – they are your standard, classic chino.  Another good option is J.Crew outlet.  As for the new 5-pocket trend, I like it.  I think they are fine pants, but they really fit more into the jeans category, and should be worn in lieu of jeans, not pants.

Secondhand Options: Plenty of pants options at Goodwill.  I highly recommend looking through the pants when you are on the hunt.  Make sure to give them a good once over.  Cleanliness is next to Godliness. Related image

Jeans:  You need at least one pair of good, dark jeans.  The type of jeans that you can wear with loafers and a sport coat.  Don’t make this hard: go to a department store (I go to Macy’s) that carries Levis and find the fit you like best.  Whether it’s 501s or 511s, get a couple pairs of darkest shade you can find (NO WHISKERS), take them home, wash them inside out, do not dry them (ever) – hang them up to dry.  Once they are dry, take them to the tailors to have them hemmed to the right length (slight break – no more, no less).

Jackets:  For the adult world, you’ll need a sport coat, a vest, and a coat that is office appropriate.  For a sport coat, I highly recommend getting a nice navy option.  I’d suggest spending a little more here as you’ll end up wearing it quite a bit.  You can get a good option from J.Crew – their Ludlow line is nice, and has a good price point.

From a vest standpoint, don’t think too hard.  Grab a fresh, clean Patagonia Better Sweater or Nano Puff.  Black, Grey or Navy are easy because they go with everything.

For a coat option, I highly recommend the Orvis Barn Coat.  It’s on sale for $98, and is a great outer layer vs. the elements.  And it will look fine in the office.  After your first (or second) bonus, you can upgrade to a Barbour or a Beckbe Blakely.

Secondhand Options: To be honest, I rarely find coats or jackets at Goodwill.  I wouldn’t rely on Goodwill to fit these needs.

Shoes:  To get started with shoes, you need a good pair of brown loafers.  You can wear them with almost anything, and they won’t break the bank.  And I mean real loafers – not drivers.  Drivers are casual, and should only be worn in casual environments.  Onward Reserve’s Pace Bit Loafers or the Martin Dingman Old Row Penny Loafers are perfect options.  Cole Haan’s Pinch Penny Loafer is another classic.

Secondhand Options: Good luck.

Accessories:  So you are on your way.  As for accessories, buy quality, and buy pieces that are transitional.  Navy blue Gold Toe socks (don’t wear colorful socks.  Seriously.).  A good brown belt that matches your loafers.  A pair of sunglasses that don’t have blue lenses.  A Colonel Littleton leather wallet that doesn’t velcro shut.

Since you are starting to build your wardrobe, it’s important to take care of everything.  You will need to dry clean some, which is fine, but you can extend wear between cleanings by giving your shirts and pants an ironing at home.  As long as there aren’t any smells or stains, use a good iron (this is all you need) to get all the wrinkles out.  Buy a few Tide sticks and put one in your briefcase, one in your car, and keep a couple at home.  Pesky stains are much more manageable if you treat them right away.

Otherwise, take care of your stuff.  Hang your shirts up after work.  Don’t throw your pants on the floor.  Use shoe trees in your loafers.  The better you take care of your stuff, the longer it will last.  And that’s good for your wallet.

Lastly, take care of yourself.  Get a good haircut.  Watch your diet.  Exercise.  Read a book a month.  Go to church.

This should get you started.  Remember: as it relates to dressing well in a professional environment, those that need to notice how you look, will notice.  Put yourself in a good spot.

P L E A S E    S U P P O R T    O U R    P A R T N E R S :



  1. ACM
    01/21/2019 / 7:50 AM

    Great stuff, as usual. 

    • JRS
      01/22/2019 / 2:24 PM

      Thanks my man.

  2. Scott
    01/21/2019 / 8:32 AM

    Awesome advice. Way too many folks coming into work world think they can go half way and look worse than if they didn’t try. 

    • JRS
      01/22/2019 / 2:25 PM

      I see it all too often…

  3. J.T. Lancer
    01/21/2019 / 8:43 AM

    Have more traditional dress pants fallen out of favor? They dress up any sport shirt and I find them more comfortable in warmer months

  4. JSP
    01/21/2019 / 8:49 AM

    Excellent article I wish I had read way back when. Totally on point. 

  5. RBG
    01/21/2019 / 8:51 AM

    Really solid advice. Nothing worse than the too hip dude who is trying to look like Esquire or GQ dressed him. People notice and it matters how you look. Nothing too on trend. 2nd the church part. Helps keep Saturday night under control and there’s nothing wrong with a hangover at church. A good priest preacher rector will understand and will probably be jealous. You can nap in the afternoon and the bloody Mary’s will be better when you meet your friends for brunch.

  6. OhioHead
    01/21/2019 / 9:55 AM

    Peter Miller makes an excellent khaki style pant (multiple color options) that can consistently snagged for about $50 to $60 @ Nordy Rack, the inseam is approximately 36” inseam so will need to be tailored.  I also suggest a dark brown pair of chukkas that work w/ khakis & jeans.
    Great post RCS!

  7. whiskeydent
    01/21/2019 / 10:32 AM

    If you have an odd shoe size (ex. 14B like me), Allen Edmonds is your best bet. Go to one of their stores and tell the sales person you are trying to figure out what last is best for you. They’re usually very helpful and knowledgeable. Unless there is a big sale going on, don’t buy anything. Instead, watch for their major sales online — especially the end-of-season ones.  You can also consider buying a pair of “seconds,” though there are risks involved. AE has some dressier loafers that cover a lot of the casual-to-business territory. They also have some nice chukkas as suggested above. Most importantly, the quality is good, though not Alden great.

  8. Trip
    01/21/2019 / 11:58 AM

    +1 for the “Structure” reference.

    • JMR
      01/21/2019 / 2:07 PM

      Man, would a 22-23 year old even remember Structure? I feel old. 

  9. HLL
    01/21/2019 / 7:22 PM

    I hope you or some readers have suggestions for me. I have a few Barbour jackets – but am looking for a camel hair/wool type of jacket, Barbour length or mid thigh and not with all the chore jacket-ish type of pockets. But also not just for the boardroom and super dressy. Seems like a lot of details. But if you or anyone has ideas or a brand or specific jacket to check out let me know. Thanks 

    • Trip
      01/22/2019 / 12:12 PM

      Have you considered a duffle coat, like one from Gloverall?

  10. 01/22/2019 / 9:25 AM

    Good post. I learn something totally new and challenging on blogs I stumbleupon everyday.
    It’s always interesting to read through content from other
    authors and practice something from other web sites.

  11. Mr. Wonderful
    01/22/2019 / 9:58 AM

    I would add that every grad needs one good suit.  Solid blue or grey, simple and traditional in cut and fit.  This can be worn to interviews, weddings and funerals and will make you stand out in a positive way.  As someone who hires serious people for serious work I tend to give a leg up to those who understand dressing for the occasion.

  12. Michael Kilkenny
    01/22/2019 / 1:02 PM

    I highly recommend a book called Dress for Success by John Molloy . I was issued a copy when I was stationed @ the pentagon in 1976. Really old school classic ideas. Has been a fashion bible for me over the past 40+ years and holds up well today. 

  13. Madison Roberts
    01/23/2019 / 6:38 PM

    I’m saving this post for when my boys get grown.  They’re 11 and 8 right now, but your advice is timeless. Well done! 

    • OhioHead
      01/25/2019 / 11:55 AM

      Start teaching them now and you will not need this post in 10 years……my boys know which suit/sport coat buttons to button already.

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