The truth is, no man needs 20 pairs of shoes.

Hell, most men could get away with much less..

And if you’re interested in creating a lean wardrobe, stocked with versatile, interchangeable pieces, you should strive for fewer choices, not more.

In fact, you only need six pairs of shoes, but a very specific set of six.

Check out the list, then leave a comment telling us which shoes you’re missing, what shoes you own that aren’t totally necessary, and what others (if any) you would add to this collection.

Need the shoes now and no time to read? Here are my recs:

Note: These shoes are listed in order from most casual to most dressy, with a more pricey and a more affordable option. Athletic or activity-specific shoes are excluded… When it comes to finding the best tap dancing / climbing / boxing shoes, you’re on your own.

White Canvas Sneakers

The perfect casual shoes, these can be worn with or without socks and are great for casual, warm weather situations. Think weekend errands, poolside days, beach trips, barbecues and good old fashioned chilling.

Oh, and these make a great substitute for your brown leather flip flops.

canvas shoes

Light Brown Boat Shoes

A step up from white canvas shoes but still casual, boat shoes should usually be worn without socks. You can wear them with shorts, chinos or casual jeans. You can’t go wrong with tan or brown, but feel free to get creative with colors and styles.

boat shoes

Medium Brown Ankle Boots

The desert boot (or chukka) might just be the most versatile men’s shoe on earth. You can wear a brown ankle boot with jeans, chinos, cords or trousers. You can dress them up, down and everything in between.

My Cole Haan Glens are probably my favorite pair of shoes, but you can’t go wrong with the trendy-yet-timeless Clarks Desert Boot (especially in Beeswax).


Rich Brown Loafers

Boat shoes are great, but you really shouldn’t wear them with trousers or in business casual environments. Loafers, on the other hand, are perfect for those situations. They’re easy to slip on and off, which is nice when you’re running late (or trying to get through airport security). They’re dressy enough for almost any professional setting, but they’re still one click below Oxfords

Don’t just reserve loafers for work, though. You can upgrade your warm weather casual looks by swapping out those boat shoes or sneakers for a pair of leather loafers. Bonus points if you ditch the socks. Just make sure to do it right.


Brown Wingtips

These are your work horses. Your go-to dress shoe. Your wingman (well, wingtips, at least). You get the point. If you work in an office, you probably wear some combination of jacket/button up shirt/trousers every day. Brown wingtips will almost always work with these outfits.

Go for something on the darker side, as opposed to a walnut or cognac color. Don’t be afraid to wear a shoe with some decoration.

If you’re going to splurge on any of your six essential shoes, you splurge on these. It will be worth it in the long run to buy resoleable shoes. That said, there are plenty of affordable options.

wing tips

Black Cap Toe Oxfords

If brown wingtips are the practical, fuel-efficient sedan you drive to work everyday, black Oxfords are your motorcycle that only leaves the garage on weekends. Because black shoes are less versatile (and often more boring) than brown ones, you simply won’t wear them as much.

But when you do, it very well may be a special occasion, and you want to look good. So buy nice shoes that will look great for the long haul, and make sure to keep them polished.

You can choose a plain toe or cap toe, but stay away from the broguing, or decoration. After all, these are the shoes you will wear to black tie events, funerals, etc.

black cap toes

Do you have all of these shoes?

Keep in mind that these colors are just guidelines. If you prefer dark brown or blue boat shoes and tan suede desert boots, knock yourself out! Just make sure to diversify your browns so you don’t end up with three different styles of shoe in the same exact shade.

If you buy smart and focus on what shoes you actually need, rather than what’s on sale and what could go with some of your outfits, you can get away only owning these six pairs of shoes.

Once you have this basic arsenal of footwear, you are free to expand and buy some work boots, monk straps, etc. But you won’t have to if you don’t want to. That’s the beauty of a lean, versatile wardrobe.

Would you add anything to the list?

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88 Responses

  1. HW on

    Good list, though if it were me, I’d definitely add a pair of winter boots on there for people living in colder climates. If you’re trying to stick to 6, I’d probably swap them out for the boat shoes or loafer, but that’s because I generally dislike slip-on loafers.

    • Brock on

      That’s a good swap. Also, you could swap out the loafers or ankle boots for a pair of work boots (Wolverine 1000 miles or something similar). Depends on how casual/dressy you are during the week.

    • Barron on

      Yeah, good point, it’s dependent on climate. If you’ll wear boots more than boat shoes or loafers, by all means, swap one out. We tried to keep it relatively middle-of-the-road in terms of suggestions, and assumed a temperate climate.

  2. Joshua on

    How do you wear all these each day? Wingtips on Monday, loafers on Tuesday, sneakers on Friday? Or Wingtips on all weekdays?

    I have 3 pairs of Allen Edmonds Strands in 3 shades because I want to maintain consistent style each day but for, longevity, avoiding wearing the same pair everyday.

    • Brock on

      Hi Joshua,

      If you’re wearing a suit and tie everyday, you might need to double up on the formal styles. For me, a typical week looks like:

      M – Oxfords
      T – Wingtips
      W – Oxfords
      Th – Loafers
      F – Boots
      S – Boat shoes
      S – Sneakers

      The wingtips and Oxfords are interchangeable for me. Just depends on what pants I’m wearing. The boots and loafers are both “smart casual” in my opinion, so they’re pretty interchangeable too.

      Same with the sneakers and boat shoes. They’re both pretty casual.

      I’m not saying you shouldn’t double up on these for longevity, or get different colors or a shoe you love and wear a lot. My point is, most guys can totally get away with these 6 pairs. Definitely these 6 styles.


      • Joshua on

        OK. I could see how this could work.

        I decided to go with “uniform” with my wardrobe. I wear my Strands to work and to play. Only a pair of sneakers.

  3. Matt on

    I can’t live without my Chelsea Boots. I live in the midwest, they keep me warm, offer great traction, and the right pair would not look out of place with a winter suit.

    I work in a casual office, so I am not sure how these would fair with the suit-and-tie crowd. Your thoughts gents?

  4. Quentin on

    I’ve got the brown brogues (Allen Edmund Strand Walnut) and the black oxfords (Cole-Haan). I don’t do white canvas; instead I’ve got green cons, grey custom cons, black vans, black/blue vans. I agree with Matt; I can’t live without my black Chelsea Boots. I wear them with any color of jeans and a black T Shirt. I have tan Clarke ankle boots. So I’m just missing the brown loafers and brown deck shoes from the original list. But my all-time favorites are my brown Frye 12R harness boots in Gaucho Brown.

  5. Vladimir on

    Great list! I’d say I own all, except for the brogues…and instead of desert boots I own an Adidas Climatex Boot which goes for my rugged outfits. The downside is that its completely outdoorsy and unclassy for a smart casual look. But anyways, there’s one more type of shoe that hasn’t been included – sports shoes. Though yes a sneaker can be used – I keep lightweight outdoor shoes for running and exercises.

    I used to own engineer boots as well – but in the end they are heavy, too rounded (the steel toe) to look casual and you can’t polish them.

    But my most favourite shoe would still be these brown Camel oxford shoes that come with a sporty sole – it looks classy and it can be used for a run/sporty activity if the need arises.

  6. Peter Gahan on

    My must have shoes are a pair of brown Hush Puppies. Comfortable and can be worn in formal or leisure situations. I disagree about your tennis shoes. No one should wear sports shoes except when playing sports.

    • Brock on

      Never worn hush puppies, myself. Agreed that tennis shoes should only be worn for sports or working out. But canvas shoes are not tennis shoes (not sure if that’s what you meant).

      • Peter Gahan on

        I don’t wear white shoes, and automatically assumed the first picture were trainers/tennis shoes. Have never seen white canvas shoes. mine are blue.

  7. Majid Ur Rehman on

    I own a black plain toe oxfords and a black loafer both from hush puppies. I have another loafer again from Hush Puppies in grey colour. I have black sandals from Caterpillar. I have brown sneakers type shoes from Clarks.
    For outdoor I rely on Clarks sneakers or grey loafers or cat sandals. For office I only wear black Oxford plain toe. Or sometime black loafer.

  8. David on

    I like this list. I agree that for us living in the north we need a boot. It is tough finding something that isn’t huge, yet warm and also professional looking. Also, I would say stay with these color choices. My first splurge out of college was a burgundy pair of Allen Edmond’s cap toe. They scream 1990’s. I don’t wear them much but I cant stand the thought of parting with them either.

      • david on

        Color. I can’t remember the last time I saw anybody wear burgundy. I’m not sure what I would even wear with them to be honest. I no longer have the navy blue double breasted suit I often paired it with.

        • NC on

          i have a pair of burgundy florsheim berkleys and they are definitely one of my go to shoes. very versatile at both the office and the beaches and the color gives it an interesting depth.

    • Jason on

      Lol? Seriously? That comment makes you look desperate and is a bit of a turnoff. I like your designs but you haven’t been around long enough to warrent serious consideration. Let your products stand on thier own merits and stop nipping at the heals of your opponents like some insecure chihuahua.

    • Marshall Lilly on

      Is this really an actual comment from a real company? Absolutely no way I’d give my business to a company who thinks behavior like this is ok.

  9. Peter Gahan on

    I would also add that a pair of walking boots is essential. Living where it snows, rains seems to be generally miserable a lot, a sturdy pair of waterproof walking shoes is fantastic. Waterproof and keep the rubbish out. I often go to the office in them, with my Hush Puppies waiting for me.

  10. Sirilly on

    I had a pair of desert boots once, they fit nice quite nicely but I’ve always found them to be too bulky at times so I gave them away. I know boots are bulky in nature but db’s just aren’t my cup of tea. So I would personally switch out the desert boot for a shoe more suited towards bad weather conditions (L.L. Bean Boots), and rely on my driving shoes for a little more zest. Speaking of which, do you consider driving shoes to be a good variation of the penny loafer? Because mine look just like them expect for the sole. Penny loafers look great, they’re just too click-clacky for me so I’ll leave that to the dress shoes only. One more question, I’ve always felt like with black oxfords you’d have to have a black suit too. So could one still be dressed appropriately for a funeral or what have you when a pair is worn a navy or charcoal gray suit?

    • Brock on


      I hear ya on the bulkiness of desert boots, but there are some slimmer options, like the J. Crew Macalister. Drivers are very similar to loafers, but loafers can be dressier, depending on which ones you buy.

      It’s a controversial topic, but black shoes are (in my opinion) less versatile than brown ones. But, you can wear them with black, charcoal, grey or dark blue suits. Navy and black can be a pretty sharp look.


  11. carlos on

    I have some medium-brown Nordstrom 1901 driving shoes. Do those count as boat shoes, loafers, or something in-between?

  12. justinong1 on

    Great article! I’m having a tough time visualizing chukka boots with trousers. Can you really wear CDB’s in beeswax with wool trousers or are you really just referring to the sleeker, dressier chukkas?

    • Brock on

      You may have missed this: “Athletic or activity-specific shoes are excluded… When it comes to finding the best tap dancing/climbing/boxing shoes, you’re on your own.”

  13. Michael Anderson on

    Obviously sissy crap. What about work boots and house shoes? Useless web post and I have no idea why.

    • Barron on

      I’d defer you to Brock’s comment above (and also to the disclaimer in the article), but in case you don’t see it:

      “Athletic or activity-specific shoes are excluded… When it comes to finding the best tap dancing/climbing/boxing shoes, you’re on your own.”

      But yeah! Totally useless web post! What sissy crap!

  14. Ryan on

    Simple. Classic. Timeless. Great article Brock, been reading your stuff for several months now and I truly enjoy your work on your site and here as well. Normally I don’t leave comments but seeing all the trolls on here who need a lesson in actual reading and not just skimming through the info, thought I’d throw out some support. Love the choices and recommended color options you selected and couldn’t agree more. Obviously your not going to mow the lawn in any of these selections. Keep up the good work.

    • Brock on

      I appreciate the support, Ryan! I didn’t know this was such a touchy subject, haha. Thanks for the kind words and for reading my stuff.

  15. Joe on

    Nice article. One point. As we age we need sturdier footwear. Redwing is a good line, and these days carries a lot more that they used to in terms of styles.

    • Brock on

      Good point, Joe. I’ve actually been waiting to buy a pair of Iron Rangers or 1000 milers. They’re definitely an investment, but so durable and versatile.

  16. notfeelinthose on

    From my experience boat shoes are usually worn by jerks, so I wouldn’t want to be caught dead in those…

    • Barron on

      Kinda like how it seems all BMW drivers are assholes on the road, so I’d never want to be caught in an M3?

      Sike, I love M3s. Your comment’s a bit of a generalization, but to each his own.

  17. Doug on

    Thanks for the awesome article, Brock! I’m just starting to think about style and this was very helpful.

    Out of curiosity, is there any reason you’d go with a wingtip here over, say, a semi brogue?

    Also, what would you think about this as a substitute for the boat shoes? They seems like a clever twist to me that could fulfill a similar role, but my calibration isn’t terribly good yet.

  18. bob on

    for my travelling situation I can have only 4 pairs, absolutely need flip flops for the beach, tennis shoes for playing tennis/going to the gym, that leaves me 2 pairs??? don’t wear a suit to work, but need to dress smart every now and then for a business meeting or nice restaurant/night out. mostly need to be able to wear with jeans/chinos/shorts, I’m thinking canvas sneakers & brown loafers?

  19. Paul Abrahams on

    For my first purchase into casual smart I’m thinking ankle boot in Bordeaux/Oxblood. Then a pair of brown brogues or cap toes. For summer a pair or two of espadrilles will do me and of course the obligatory aussie thong.

  20. Jason on

    Nice post. I’m one of those guys trying to lean out his closet. Do you think a pair of brown wingtip boots could fill the same role as brown wingtips. I like wearing boots and all things being equal (color, shade, broguing, etc) when would I not be able to wear the boot version of a shoe? Thanks!

  21. Only Moses on

    Fantastic post, many thanks. As a real style newbie, who’s still in the experimentation phase, it gave me a nice bit of positive feedback for three of my recent purchases; Tan Loafers, Boat Shoes & Brown Chukkas :O)

  22. Only Moses on

    Thanks again Barron, with your advice in hand I just added a pair of 100% leather wingtips to complete my shoe line up pictured below. Any feedback on my choices would be gratefully received :O)

  23. Guest on

    All six pairs are hard to argue about. Well, maybe you don’t really need both loafers and boat shoes you you are trying to minimize your collection. In fact, they all are standard for all-shoes-you’ll-ever-need lists (I’ve seen about 10 such lists). And just like most other all-shoes-you’ll-ever-need lists, this one is only good for someone who lives in warm climate, always travels by car, works an office job and never goes outdoors. But what if you live in a place where it snows in the winter? When temperature drops below -15 C, no ankle boots will be any good. What if you live in a place where it can rain heavily? What if you do long walks (be commuting by foot, hiking in the hills or walking a dog)? What if you ride a bicycle or a motorcycle? What if you are doing sports? There’s no winter boots, dress boots, rain boots, work boots or sports shoes in the list, and most men will need at least one of them way more often than cap toe oxfords or boat shoes.

    • Collin on

      The author is coming from a perspective to spice up your wardrobe or style, not so much practicality or shoes for specific use.

    • Kelvin on

      Well I have had a pair of Raplh Lauren for 4 years with faux fur lining inside. They look nice as hell. They have endured through cold winters and they are comfortable.

    • Brock on

      As noted, the list doesn’t include activity-specific (i.e. sports) footwear. I live in DC, which gets pretty cold, icy and wet for part of the year. Most of my leather shoes do okay through the winter, but I have a pair of water proof boots too.

      If you live in a colder climate, I’d say swap the loafers/boat shoes for a pair of winter boots and you’ll be fine with six pairs.

  24. Nico Buzzi on

    Very interesting, I totally agree. I have one doubt regarding boat shoes and loafers. I’m not sure if leather or suede. Leather is more durable I think and it requires less maintenance, although I’m not completely sure. If I bought suede shoes, what belt should I buy?

    Thanks for the advice man!

    • Brock on

      For boat shoes, I agree – go with leather. I do have a pair of suede loafers (Jay Butler) and suede ankle boots (J. Crew) that I really like.

      But they’re not as versatile or durable and their leather counterparts.

      As long as the belt kind of matches in color, it doesn’t really have to be suede. I’ll wear woven belts with suede shoes, which is a nice texture.

      Then again, suede belts are pretty sweet.

  25. Carlo DG on

    My grandpa shoes collection looked like exactly like that! I am 57 and my boots and shoes looks much more updated than what you have suggested here.

  26. Hiren Vyas on

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  27. Epic Understated on

    Hi Barron,

    I would like to bring your attention to the Blucher Camp Moc as the better alternative to the Boat Shoes. A great article by Primer Magazine

    I agree these blucher mocs can be worn all year round unlike the boat shoes.

    I guess you may need to update your list on this website now. Thanks.

  28. renindy on

    i like the post! i have the oxfords, too many pairs of sneakers, and need to uprate my boat shoes. just can’t bring myself to do the wingtips. So I have a pair of brown loafers and a black pair. Can’t argue with the timelessness of the six featured.

  29. Mala on

    So I’ve reduced my self to four shoes (more like 3.)

    I’m never in an environment that DEMANDS black captoe oxfords. I am a minister so funation and simplicit is key here. Here we go.

    1. Ultra versatile black chelsea boots, from denim to a charcoal suit.
    2. Brown wingtip boots. Casual and suit wear, plus brown just looks great.
    3. Work boot. Currently I have desert boots which are great for the country setting I find my self in frequently. Once they wear out I’ll replace them with the Timberland Britton Hill Chukka boot.
    4. More of a bonus honestly, Classic navy vans. Because sometimes boots aren’t cutting it. I say bonus because vans tend to make me look 15 years old so I primarily wear dressier clothing.

    Why no boat shoe? The function of a boat shoe has been combined with Vans because the waffle print was designed for decks and boats. The casual but slightly dressy nature has been thrown in with the desert boots.

  30. Michael Smith on

    I think this is a great post, and anything that helps men dress better is always needed.

    However, this is the most boring group of shoes I’ve seen in my life.

    As your style matures, you should find enjoyment in wearing every piece of clothing you own. I doubt anyone would get exited at the thought of wearing any of these.

    Shoes are considered to be the most important part of a mans wardrobe. As they have the ability to make or break any outfit. And it’s the FIRST item others notice.

    Every time you put on your shoes you have an opportunity to:

    A. Blow an outfit,
    B. Play it safe, and wear shoes that are “timeless” (Aka boring but not bad),
    C. Nail your outfit with an AMAZING pair of shoes.
    This is most important when men are becoming aware to style as the other items will most likely be bland and boring anyway. For example, dark slim jeans and a grey sweater. Classic, timeless and if you pair it with brown chukkas, your safe. But you can pair it with a pair of boots that are unique but classy, your outfit could go to another level.

    Just thoughts from my journey into my own style.

    • Barron on

      We’ve approached this article from the beginner’s point of view. What are the basic types of shoes that would give him a well-rounded starter collection? I think any guy can expand beyond this list, but if you’re just starting out, having these staples would benefit any guy’s growing wardrobe.

      • Michael Smith on

        I completely agree. If he’s starting out and just getting his feet wet (no pun intended), this is the list he needs.

        Love your blog