Hey Gents,

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The following article is from Brock McGoff of The Modest Man. Take it away, Brock!

six pairs shoesIf you’re reading this article, it means you’re interested in improving your style.

Maybe you’re a style expert looking for new tips, or maybe you’re a total noob.

Either way, the amount of information and advice available can be overwhelming, and it’s easy to start feeling like you need to buy a bunch of new clothes all at once.

I’m a style blogger, but I’m not immune to this either.

Just the other day, I was browsing through the threads on a popular men’s style forum, researching a new pair of shoes, and I stumbled onto a thread about people’s closets.

Forum members were posting pictures of their wardrobes, and I was in awe of the sheer volume of clothing some people have.

I’m talking racks of clothes, and what shocked me most was how many pairs of shoes some of these guys have. Stacked in boxes from floor to ceiling, many of these men had accumulated 20, 30 or 40 pairs of shoes!

Don’t get me wrong, I love shoes. They’re one of the best parts of a man’s wardrobe. If I had the closet space and the budget for it, I’d probably have stacks of shoes too. But this seems excessive.

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 less 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.

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
top: Converse Chuck Taylor, bottom: Lands’ End Canvas Oxford

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
top: Gold Cup Original Boat Shoe, bottom: Sperry Top-Sider Original Boat Shoe

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).

top: Cole Haan Glen Chukka, bottom: Clarks Desert Boot

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.

top: Johnston & Murphy Ainsworth, bottom: Sebago Grant

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
top: Allen Edmonds McAllister, bottom: Johnston & Murphy Tyndall

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
top: Allen Edmonds Park Avenue, bottom: Johnston & Murphy Melton


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.

Do you have all of these shoes? Would you add anything to the list? Leave a comment below!

PUBLISHED April 3, 2014

Brock is the founder of The Modest Man and the author of Short Man Style. You should Join his newsletter for more tips on how shorter gents can dress better by finding clothes that fit.

  • HW

    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.

    • http://www.themodestman.com/ Brock

      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.

    • http://effortlessgent.com Barron

      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.

  • Joshua

    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.

    • http://www.themodestman.com/ Brock

      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

        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.

  • Matt

    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?

    • http://www.themodestman.com/ Brock

      I think you can pull those off with a dressy outfit. Maybe not during the warmer months…

    • http://effortlessgent.com Barron

      Yep, chelsea boots look great with suits.

  • Quentin

    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.

    • http://www.themodestman.com/ Brock

      Those are straight sexy. I just bought my first pair of Frye shoes… taking a while to break in but they’re quality.

  • Brian williams

    Sorry, the only pair of shoes I need is a good pair of Vans.

    • http://www.themodestman.com/ Brock

      Maybe if your name is Tony Hawk.. haha, I kid. Whatever lifestyle you can lead with one pair of vans, I’m jealous.

  • Vladimir

    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.

  • Peter Gahan

    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.

    • http://www.themodestman.com/ Brock

      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

        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.

  • Majid Ur Rehman

    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.

  • Rfalcon

    I have a pair of gortex hiking boots and Merrel trail shoes. They cover every need.

    • http://www.themodestman.com/ Brock

      Every need, huh? Can you get me a job where you work?

  • David

    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.

    • http://effortlessgent.com Barron

      Is it the color, or the style of shoe that screams 90s? I’ve seen a few models in burgundy that look great.

      • david

        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

          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.

  • http://www.paulevansny.com/ Paul Evans

    lol @ allen edmonds

    • http://www.themodestman.com/ Brock

      Uh oh, Paul Evans is acting up in the comments section again ;). Do you have smaller sizes in stock yet?? AE does…

      • http://www.paulevansny.com/ Paul Evans

        They got sizes all right. Missing some other key ingredients though, style being one of them. We go down to 7 with our Brando restock.

        • Jesse William

          Unfortunately for you, class is always more important than style.

    • Jason

      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

      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.

  • Peter Gahan

    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.

  • Sirilly

    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?

    • http://www.themodestman.com/ Brock


      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.


  • carlos

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

    • http://www.themodestman.com/ Brock

      I’d put those in the casual loafer category.

  • justinong1

    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?

    • http://effortlessgent.com Barron

      Just the dressier chukka boots. The Clarks Beeswax versions are too casual.

    • http://www.themodestman.com/ Brock

      Yeah, like Barron said. I wear my Cole Haan ankle boots with trousers all the time. They’re much dressier than CDBs though (narrower profile, more shine, etc.).

  • ron

    Would not wear a pair of these if they were free

    • Brandon

      A pair of what?

  • Keeping it real

    I guess we’re suppose to muck stalls and cut grass in boat shoes or wing tip?

    • http://www.themodestman.com/ Brock

      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.”

  • Michael Anderson

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

    • http://effortlessgent.com Barron

      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!

      • http://www.themodestman.com/ Brock

        What he said ^^

    • Toby_W

      You need a website to tell you whether you need work boots?

  • Ryan

    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.

    • http://www.themodestman.com/ Brock

      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.

  • Joe

    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.

    • http://www.themodestman.com/ Brock

      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.

  • http://dbakeca.com Dbakeca Italia

    very true

  • notfeelinthose

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

    • http://effortlessgent.com Barron

      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.

  • really

    So which pair should I run on the treadmill with?

    • http://effortlessgent.com Barron

      The pair that falls under the disclaimer:

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

      • Mr. Effectzoluwapo


  • Doug

    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? http://www.vans.com/shop/mens-shoes/canvas-zapato-del-barco-navy They seems like a clever twist to me that could fulfill a similar role, but my calibration isn’t terribly good yet.

  • bob

    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?

    • bob

      ha, just saw ur hawaii article, maybe i’ll go monkstrap.

  • http://www.google.com/profiles/paulabrahamsmusic Paul Abrahams

    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.

  • Jason

    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!

  • Javier

    I loved the loafers, the mahogany ones. But can I use them with any color? Shirts?

  • Only Moses

    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)

    • http://effortlessgent.com/ Barron

      nice choices! Those will serve you well.

  • Only Moses

    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)

  • Brigita

    Thanks for those tips for wholesale fashion shoes. 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.