Building a Wardrobe: Foundations

Being a bit of a clothes horse is nothing new to me.  I’ve dialed in my style over the years, and have learned a lot of lessons.  I’ve pulled the trigger on pieces that had no place in my closet, and missed out on even more.  Still, I’m happy with the state of my closet, even though it is a constant state of fluidity.

I went through a ‘rebirth’ in my wardrobe many years ago, and have been curating ever since.  After going through the rebirth and the work associated, I’ve learned quite a few lessons.  Whether it be to know when to buy at retail, knowing where to find the deals, and having a few tailors helping me out, there are more tricks to a good wardrobe then just a closet full of brand name goods.  One of those tricks is having a good foundation.  There are pieces of a man’s wardrobe that are absolutes, and create a building block to take it in your direction; to create YOUR style.

I’ve put together a list of the ten pieces you need as a foundation to your wardrobe.  This is my list, and obviously up for debate, but for now, here you go:

1 A blue blazer.

To me, this is the cornerstone of any man’s wardrobe.  It’s hard to describe the importance of a blue blazer.  You can put it on over almost anything, and it immediately formalizes your look.  It’s also wearable in nearly 80% of situations where you need to present yourself appropriately – big meetings at work, church, dates, parties, events, “jacket required” dining rooms…it doesn’t require a lot of thought.

In terms of the right jacket, we’ve moved past the days of the square blue blazer with big brass buttons.  While I’m all about value proposition, this is one piece that I would recommend stretching the budget.  ALWAYS go 100% wool here.  There are plenty of good off-the-rack options, but if possible, having a blue blazer made for you is actually a good investment considering how much you’ll wear it.  For off the rack options, I would look at Brooks Brothers, but pick the right cut (I prefer Fitzgerald), Tombolini Dream for a more modern cut, or Strong Suit from Nordstrom.  I have experience with each, and can speak to the value proposition of each.  Each hit at or just under that $500 mark, which is a good price point for a wardrobe workhorse.  Should you decide to go big, head over to your favorite men’s store and have them make one for you.  The cost will end up 150-200%+ more, but you know where this is going…

2. A set of dress shirts.

When I say ‘set’, I mean the four colors that would be considered the baseline: white, blue, pink, and blue stripe.  These are the shirts that go with everything, can be dressed up or dressed down, and will never go out of style.  There has been a weird trend to stretch it with your dress shirt.  I’m not big on it, instead I opt to stick with the primaries.

With the shirts, I would stay away from ‘non-iron’.  They tend to break down way too quickly, and look dingy after a few washes/wears, especially the solid dress shirts.  Instead, go with 100% cotton pinpoint or oxford, must iron, and take care of them per the instructions.  I would recommend getting point collars on the white and blue, as they are the most formal, and button down, unlined collars on the blue stripe and pink shirts, as they can be dressed down.  My rule of thumb is that if a collar is lined, it should be dry cleaned (no starch!), and unlined can be washed, hung dry, and ironed.  For longevity, it’s not a bad idea to wear a v-neck undershirt.  It’ll soak up most everything that would cause damage to your shirts.

Again, custom shirts are great, but they can get expensive.  Even though the vast majority of Brooks Brothers shirt collection is non-iron, there are a few choices that are well worth it: the Original Polo Shirt.  Beyond these, there are great options from online Men’s Stores like Ledbury, and Atlanta’s Sid Mashburn has an excellent online collection as well.

3. A good pair of jeans.

What I mean here by a good pair of jeans is a pair that act more like dress pants.  It’s fine to have other jeans that you can bum around in, wear with work boots, and generally beat the sh!t out of, like most jeans are made to take.  Just because a dress code says ‘jeans OK’ doesn’t mean it’s a casual setting.  Jeans can be dressed up very easily, and create a really slick look that isn’t too modern.

I would stay away from any whiskering or pre-distressed jeans in this category.  Again, it’s fine to have a pair or two as back ups, but a good pair of dark jeans is what we are going for here.  You can break them in your way.  In terms of what to look for: I like Levi’s 501 Rigid Shrink to Fits that rarely get washed, and never get dried, A.P.C New Standards, as the denim is excellent, and breaks in extremely well, and Raleigh Denim Jones Fit, which have an excellent story.  The key to this category of jeans is to get them tailored to your body.  Don’t go skinny; opt for slim.  I like a 7.5″ leg opening with almost no break, as it looks the best with dress shoes and loafers.  Care for these delicately…  I would only soak these to wash, and never let these touch the dryer.  Eventually they’ll become a second skin, and a major player in the rotation.

4. A pair of brown loafers.

The older I get, the more I wear loafers.  It’s almost like I’ve forgotten how to tie shoes.  On rare occasions loafers can be worn with suits, but on ALL occasions loafers can be worn with anything else.  A good pair of brown loafers is an extremely worthwhile investment for building a wardrobe.

There are a few types that work here: a penny loafer, a bit loafer, or a tassel loafer.  In all cases, I highly recommend a leather sole, good welting that can be re-soled, and quality leather that can be conditioned and polished.  For a penny loafer, the Old Row Penny Loafer from Martin Dingman is excellent.  Bit loafers add just a bit of flare to the penny, and my pick is from the fine folks at Oak Street Bootmakers.  They knocked it out of the park – the vamp is just right, the leather is great, the toe box is sleek, and the price is just right.  Tassel loafers are the dressiest of my recommendations, but what was once your grandfather’s shoe of choice is making a big comeback.  No question here that Alden is the way to go.  It’s an investment, but you won’t find a better tassel loafer out there.

5. A grey suit.

Unless you are in a few professions, suits simply aren’t worn that much anymore.  However, it is extremely important to have a good one for the rare(?) situations where one is needed.  I would argue that men are most vulnerable when wearing a suit – because they don’t wear them that much.  Having a suit that fits well, is somewhat stylish, and of good quality will give you confidence when stepping out.  If it’s old, out of date, and/or ill fitting, you may as well stay home.  Remember what Prime Time said… ‘if you look good, you feel good….’.

A good suit doesn’t have to cost a ton of money, as it’s more about the fit.  I would recommend going with a medium to dark grey for your main suit.  I also like Navy, but I think that’s better for your #2.  Grey is extremely versatile, and can be dressed up like a tuxedo (with black shoes and belt), or almost as a neutral with a striped shirt and solid tie.  In terms of what to get, I recommend going more classic rather than trendy.  Hickey Freeman’s B-Series Beacon suits are extremely handsome, and an excellent off-the-rack option.  The Loro Piana wool and updated cut is just right.  A custom suit is always an option, but that isn’t for everyone.  The Brooks Brothers 1818 standard 2-button suit is great, and there are always coupons available or big sales to help cut down the cost.  With your suit, get a good hanger and storage bag, since it’ll probably spend a lot of time in your closet.  Doing it right means that you’ll be at the top of your game any time you pull out the suit of armor.

6. A good pair of khakis.

Don’t kid yourself, just because jeans are more acceptable and 5-pockets have become popular has nothing to do with the diminishing return of a good pair of khakis.  Good khakis are in an exclusive category of their own.  I’m not referring to Duck Heads here – I’m talking about a nice pair of twill dress pants that happen to be in the khaki shade.  These pants become workhorses in everyday situations, and go with just about everything.  A good fitting pair is a mature look, and will serve you extremely well.

In terms of the pants, when I say ‘good’, I mean a pair of khakis that have an alterable waistband, NO logos, and constructed of substantial twill fabric.  They should fit well, like the jeans above, and keep their shape throughout the day.  Personally, my favorite are Hertling khakis, which is a source for most good menswear shops like Harrison LTD in Birmingham.  Their Badge khakis are literally the nicest khakis I’ve ever seen.  Incotex/Unis are an excellent choice as well, as they are usually great right off the shelf.   Finally, Orvis did an outstanding job with their slim fit Ultimate Khakis.  They are a GREAT value for what you get.  When ordering, get them longer than you need, and have them tailored to the perfect length.  It’s worth it.  I’m anti-pleat, and do enjoy a good cuff every now and then.

7. A grey cashmere sweater.

I love cashmere.  For the longest time, I was intimidated by the supple fabric…mainly because of the price, but also because I was positive that it would be something I would ruin.  I’ve gotten over that, and have jumped into cashmere head first (a metaphor, but it would also be pretty cool to dive into cashmere).

I look at my grey cashmere v-neck sweater as a savior.  More times than not, I’m able to throw on that sweater and it immediately fixes whatever is wrong with my outfit.  It immediately dresses everything up.  My wife loves it because not only does it look good, but it feels good.  In a hurry after a long day at the office?  Throw on a grey cashmere sweater over a pink oxford with jeans and tassel loafers and you look better than 99% of the guys at the bar.  Also, it doesn’t matter if you’ve been wearing that shirt all day…(wink).  Not getting into the long vs. short fiber cashmere argument, these sweaters are priced all over the map.  Johnstons of Elgin is as nice as it gets, but you pay for it.  Alan Paine makes very nice sweaters, and the steal is from Nordstrom.

8. A pair of black cap toe oxfords.

While these will probably get worn as much as your suit, it’s extremely important to have great pair of black cap toe oxfords.  You can’t wear a good suit with bad shoes.  There’s no way you’ll be taken seriously.

There are a few that I would recommend here:  My go-tos are Allen Edmonds Park Avenues.  Simple, no frills, and constructed well enough that they’ll last for years.  Cobbler Union makes an extremely nice pair of cap toes call the Richard, which look like a race car, if that’s possible for such a classic shoe.  Care to go a bit English?  Treat yourself to a pair of Crockett & Jones Audley’s.  They are as good as it gets.  As with any dress shoes, take care of them.  Clean, polish, and always store them with cedar shoe trees.

9. A clean, white golf shirt.

It’s funny how golf shirts accumulate over time.  There are so many styles, fabrics, and cuts that it’s easy to build a stack that eventually gets out of hand.  I quit buying shirts at most golf clubs for this reason.  Too many golf shirts cause analysis paralysis.  What you do need is one, great, white golf shirt.  Great cut, no logo, and not dingy.  Here’s the argument: it takes away all dressing issues when a dress shirt is too much, and it’s hot outside.  A white golf shirt goes with everything: jeans, khakis, shorts of all varieties, and an even wider range of footwear.  Got a round of golf with your bosses, boss?  White golf shirt.  Having dinner at the beach where a jacket is required?  White golf shirt.  Heading to The Masters to watch the Par-3 tournament?  White golf shirt.

For me, there isn’t a better white golf shirt than the Chapman from Holderness & Bourne.  Yes, we’ve done some work with them here, but all the praise is very well worth it.  The shirt is cotton, the collar is perfect, and the white is just right.  You’ll want to take care of this like a dress shirt.  This one is an ace, folks.

10. A DYNOMITE tie.

There comes a time in life when you need to be taken seriously, while at the same time not causing a distraction.  All of those motif ties with beers and limes, beach chairs and umbrellas, and whatever cartoon are fine ties.  But they aren’t the tie you need.  There are going to be times when you have to knock it out of the park.  Think job interview, rehearsal dinner, Christenings, galas…any black tie optional event where you elect not to wear a tux.  This is where you bring out the big gun.

A great tie like this does not need to be expensive.  It needs to be a power tie.  I like a bold color, a tight pattern (if any at all), and most importantly: not a distraction.  Top of the food chain is Hermes, who makes very handsome, timeless ties.  I really like ties from Drake’s.  They have a great selection, and the quality is top notch…you aren’t just paying for the name.  Other options are from Ben Silver and Brooks Brothers for the uber traditional set.  Remember: the tie completes your set of armor.  It’s your sword.


This is my take.  I get questions all the time on ‘what should I do in this occasion, etc.’; conversations I enjoy immensely.  We’ll do 11-20 later, but for now, I’d love to hear your feedback.  Cheers, JRS.



  1. Nem
    10/23/2017 / 8:23 AM

    Good list of basics.  I’d add a good quality brown alligator, or at least top quality bridle leather, belt with a nice brass plate or slide buckle.  Good pants or jeans are often ruined by some ugly afterthought belt.

    • JRS
      10/24/2017 / 8:29 AM

      I knew you’d pick up on that.  I struggled with adding a belt, but I couldn’t find something to swap it out for…I’m sure you can guess what #11 is…

  2. Livingston Mimms
    10/23/2017 / 9:03 AM

    Great post. I am re-thinking my “uniform” now, which is basically PM Five Pocket pants and PM golf shirts, and in winter adding a PM pullover. This setup is a little prone to club logo overload and is also a little casual. 
    I am now (slowly) sourcing the following: 5 Blazers / Sport Coats (1 week rotation), 10 Dress Shirts (2 week rotation: Blue and White and Pink Solids and vertical stripes), 2 pairs brown bit loafers, and the worst part: socks. I hate buying socks. Add in a few Smathers and Branson belts and a black and a brown belt and you are set. 
    Also, a great option for a sweaty guy is the Thompson V-Neck T to protect your undershirts. 
    Best shops in town for MTM shirts are Miller Bros and Sid. 

    • JAG
      10/23/2017 / 3:22 PM

      Try some TM Lewin or Charles Tyrwhitt. For the money you can’t beat them. See comment below.

    • JRS
      10/24/2017 / 8:31 AM

      I like the transformation.  The Five Pockets are great, but I would add some REALLY nice khakis in different shades, get a La Matera belt instead of another S&B, and Pantherella socks.  

  3. JMR
    10/23/2017 / 10:06 AM

    I’d add a good sneaker that you can throw into the mix. Loafers are fine, even preferred, when heading out to the farmers’ market. But when your toddler makes a b-line to play in the dewy grass, you’re going to ruin that good leather. A good pair of classic sneakers (I like Onitsuka Tiger) are not only cheaper to replace if necessary, but are probably up to the task without looking like you just threw on your gym shoes. 

    • JRS
      10/24/2017 / 8:32 AM

      I agree that a sneaker is good, but I don’t know what it would replace…  Just wait for my #11-20 list…

  4. MDV
    10/23/2017 / 10:37 AM

    Oak St. has discontinued their bit loafers. The window has closed on these save for the few on the board that can still wear Stride Rites. 

  5. PLF3
    10/23/2017 / 11:33 AM

    Great list. I would agree with adding sneakers such as Tretorns. 

  6. JAG
    10/23/2017 / 3:18 PM

    Good picks. You can do a lot with all those. Add in a few variations and your wardrobe would be set. One thing for me is a crocodile black and brown Trafalgar belt strap that I just swap the buckles out on. It’s one of the only ones I wear b/c I can do it with anything. Also, I couldn’t make a list without a good pair of boots in there. Preferably some Tecovas. As for shirts, (this may be a suggestion for Livingston Mimms) I use to spend a pretty penny on my rotation from local men’s shops, Brooks, Nordstrom’s, etc. My rotation is typically 2 French cuff white, 2 French cuff blue, 2 barrel cuff blue, 2 barrel cuff white, a pink, blue Bengal, and a few other random classic Bengals with one or two ginghams. I recently got turned onto Charles Tyrwhitt and TM Lewin out of London. If you Google “Charles Tyrwhitt” the top link will be $29.50 shirts from the competing TM Lewin. I ordered a few to test them out and they’ve been great. I still order my french cuffs from Charles Tyrwhitt but I’ve started mixing in the others and I doubt I’ll have to go buy shirts again at a store unless its MTM. They do free returns/exchanges so you can easily find your perfect fit. I usually over order and send back whatever doesn’t work. Just as an example, I ordered 8 from Lewin and 6 from CT in May. I’ve worn them in regular rotation and dry cleaned them (laundered, no starch, hand pressed). They still look great and aren’t worn out at all. I’ve been very pleased. That entire purchase cost me maybe $450 (with a few initial customization’s, etc) and has been worth every penny. I love the fact that there are basically just two brands that dominate my shirt rack. 

  7. SMGS
    10/23/2017 / 11:20 PM

    Who makes the suede shoes paired with the khakis? Been looking for something similar for a while now. Thanks

    • JRS
      10/24/2017 / 8:33 AM

      My guess is that they are the Alden unlined chukkas.  They are outstanding.

  8. nachdrock
    11/04/2017 / 11:13 PM

    you feel good, you play good….you play good, they pay good

  9. RTB
    03/07/2018 / 11:33 PM

    Are we going to see a 11-20 list?

  10. B. Scott Robinson
    12/30/2020 / 12:01 PM

    Still spot on! Covid won’t last forever!

  11. CCE
    12/30/2020 / 2:57 PM

    This list still holds up, however I think going into 2021 Brooks Brothers has finally hit rock bottom. As I turn the corner towards 40, I’m in a position to really make better choices with my wardrobe, and I lean towards bespoke or semi-custom over off-the-rack for most business/business casual staples. Solid pairs of cordovan and black lace-ups are always correct and will never go out of vogue. Like RCS says, a good tailor can really make a difference when buying off-the-rack, so I recommend finding a tailor who truly knows how to reconstruct an article of clothing. Look good, feel good.

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