The Tailored Polo Shirt

June 21st, 2013

In my opinion, a great menswear outfit seamlessly blends dressy elements with casual ones.

A tailored jacket with a polo shirt is a great example.

Here’s three examples and some tips to pull it off.

    1. Soft Suit, Structured Polo


    The key to a great suit + polo look is pairing the right suit (lightweight and unstructured) with the right polo (button-down collar, deep placket, slim fit). The button-down collar is probably the most important of those details; it keeps the collar in place and standing upright, visually framing the face.

    This block-stripe polo adds a cool sporty touch that off-sets the formality of the suit, creating a look that I can wear just about anywhere.


    This tobacco linen suit might be my favorite for summer. I’ve been wearing it for a week straight (as a suit, blazer, and trousers).

    I find that lightweight fabrics are very underrated in menswear. Editors and bloggers are always writing about their excitement for F/W fabrics (flannels, tweeds, cashmeres, etc) but this Winter I couldn’t wait to break-out the lightweight goods (hopsacks, linens, silks – more on silk soon).

    I got this belt at KMart (two for $4.99 – see our “Money Can’t Buy Style” post). It’s made of cheap plastic, but I get more compliments on it than any other belt in my collection (including an $800 alligator number).


    A brown penny loafer (like these Bass classics) is the most versatile shoe a man can own, in my opinion.

    When I’m in a rush and can’t make a decision on footwear, I almost always grab these – whether I’m wearing a suit, jeans, or shorts.


    • Tortoiseshell sunglasses by Persol
    • “Tobacco” linen suit
    • Blue Block-stripe polo by Uniqlo x Michael Bastian
    • Brown woven belt from KMart
    • Brown Penny Loafers by Bass Weejun x Barneys

    2. City Chic


    If you’re wearing a jacket with tailored trousers – tuck your shirt in. Yes, even if it’s a polo. A tucked shirt looks more confident and put-together – it also visually splits your body in proper proportion (accentuating the waistline is the oldest trick in womenswear – it looks good on men too).


    3. Country Vibes


    As you may have noticed, I often gravitate toward earthy color palettes (like browns, greens, and rustic oranges), regardless of the season. I think they remind me of life back on the farm…I also think they complement my skin tone and hair color.

    I got lucky the day I found this vintage Ralph Lauren polo, from one of his epic Southwestern-print-heavy collections back in the day. It doesn’t have a button-down collar, but it stands fairly well under a jacket.

    This suit jacket is mostly silk – what I consider the most underrated fabric in menswear. It’s lighter than linen, breathes just as well, and has a sheen unlike any other fabric, which is great for offsetting textures. We have a great post on men’s silks in the works…


    Funny story about this brown silk/cotton Hugo Boss suit:

    It was the first “slim fit” garment I ever bought, on eBay in 2006, when I was wearing XXL Pelle Pelle t-shirts and Karl Kani jeans with 22″ leg openings. My girlfriend at the time, a fellow college basketball player, hated it. The pants were “way too tight”…”I can see your b-lls!”. Haha.

    So then came my first visit to an alterations tailor, to let the crotch out (we had to get creative and add an inseam gusset using the excess fabric under the hem). Long story short: the pants never got loose enough for her and that trip to the tailor was an eye-opening experience that got me hooked. Shortly thereafter I stepped up my eBay hustle (selling an excessive sneaker collection to buy slim-fit European clothing)…and today she and I remain friends :/

    C’est la vie.


    Thanks to my man Niyi for this awesome pocket square.

    I recently put together these sick new Allen Edmonds brogues using their new online custom design tool. Originally I was going to do something colorful and crazy, but I’m glad I stuck with the brown-on-brown texture blocking (walnut calfskin, brown alpine grain, and chocolate suede).


    • Tortoise shades Vintage by Hugo Boss x Carrera
    • Navajo Print Polo Shirt by Ralph Lauren (Vintage)
    • Pocket Square by Post-Imperial
    • Vintage belt
    • Forest green cotton suit trousers
    • Brown Custom “strand” captoe brogues by Allen Edmonds

    4. Business Casual Proper


    By now you’ve mastered the art of separates: a sports coat and trousers, or two complementary suits mashed-up.

    For “business casual” or a smart social event, try off-setting the formality of the tailored jacket with a polo shirt, rather than the expected business shirt.


    Similar to look 1, this polo has a deeper 4-button placket and a button-down collar – perfect for under a jacket. The bengal stripes are also a nice nod to the traditional oxford shirt.


    It’s sockless season!

    Personally, I love the feeling of good leather on my bare feet, but if you’re not ready for the real thing you can try these.


    Thanks, as always, for reading.

    Yours in style,

    Articles of Style


    Photography by Alex Crawford

    • PD

      So fresh and so clean

    • http://undefined mathieu lavoie

      Great post, I’m now a big fan of button down polo thanks to TSB.

      but designer polo can be expensive,

      I often buy some small collar button and sew them on basic polo shirt. It add structure and the overall look feel more sophisticated. I usually choose a constrasting color as well,

      Small tip for other fellows on a budget

    • Penn

      What is the make/model of the Persol sunglasses?

    • Marc


      Just wondering what’s the weight of the forest green cotton suit? I’m looking to get a cotton suit too but unsure of the weight for summer. Thanks!


      • Dan Trepanier

        Hey Marc,

        It’s a lightweight chino cotton. Not sure the ounce weight, if I had to guess I would say 8oz.

        If you’re going green, I suggest going dark in color (just a hint of green) and a lightweight fabric (it looks more natural in a seasonal fabric).


    • TO

      Was that the Hugo Boss suit from the shot jumping over the parking meter? Especially great narrative on this article, really engaging.

      Love that new blue suit jacket as shown in WIWTs previously. Just such a great shade and fabric! And it works fantastically with the grey trousers. Same with look 3.

      Found a button down polo at a thrift shop the other day ($3) from Joe Fresh- I am constantly blown away with how many awesome items they have in their archives!

      • Dan Trepanier

        Yup – great memory.

        Joe fresh…gotta show love to the fellow Canadians

    • BF

      I like the look on dan, but don’t do it myself.

      I have one MB polo (dragonflies) and its Awesome.
      I’m 6’1 190lbs 32 inch waist- athletic and a large fits nice…The waist is nicely tapered.

      Problem is, those damn things are never in stock and the vultures on ebay are trying to sell 19$ shirts for 37$

      • Dan Trepanier

        Thanks BF. Supply & demand my man…gotta get ’em while they’re hot. Even at $37, though, that’s a good buy in my opinion.


    • Tom

      Looking at your donation page for the ‘style guide’ idea, I have to mention something:

      Offering ‘exclusive posts’ on your website for cash donations is not a good method of keeping readers who prefer non-endorsed content.

      I understand your desire to create something new and interesting in the menswear community, but I am not sure if the style guide is something that appeals to the core menswear demographic. Most menswear followers prefer tumblr based fast-inspiration or content producers like putthison, four pins (your site would also fall into this category).

      $30,000 seems like a very large sum to be requesting readers to provide, so some perspective or break-down on where exactly all that money is going I imagine will improve your chances of reaching your goal.

      Could you clarify – break down the $30,000 piece by piece and also explain the concept and why it is worth people giving you money for?

      • Dan Trepanier

        Hi Tom. Thanks for your message and feedback.

        The Style Guide is exactly that: fast-inspiration with links back to the original websites. The goal is to organize all the great menswear content on sites like tumblr, and point back to the original publishers of every photo, so the users can get instant inspiration as well as find new quality publishers (in addition to discussing, shopping, etc).

        I realize 30K might seem like a lot to ask from readers, but with 120,000+ monthly readers, its less than one dollar from 25% of the people who visit our site every month for free content.

        The money raised will all go to paying our web development firm. Building a social platform at this scale takes a long time to code and develop – especially with the automated shopping associations in three price points for all products. Truth is, it’s going to cost significantly more than 30K to fully build out all the functionality, but with the 30 plus what we can invest personally, we can build the core concept and take it live.

        If you have any more questions, I can certainly elaborate via email:

        Thanks again for your feedback.


        • Tom

          After reading your response, I do believe that the style guide will appeal primarily to those learning or introducing themselves to menswear. I’ve followed this site and find the style guide to not serve much purpose to myself (actually something of an annoyance to see – not many people search a style guide for dressing themselves) and others who enjoy commentary and content but aren’t necessarily looking for price tiered ‘fast picks’ – seems like a misguided approach to the discussion. Where I’m questioning this concept: Not following why you would desire to have ‘three price points for all products’ from tumblr based content from other providers, which in turn would lead to you profiting from others ideas – and ultimately provide something (bunch of price-tiered options) I’m not sure people really want.

          • Tom

            Hiding post from display? This is the last time I’ll comment with an opinion on this blog.

            • Dan Trepanier

              No, just been traveling in Europe and haven’t had proper internet access to provide a well written response.

              Sorry for the delay – we try to get to all comments and contact forms in good time, but with the volume and our schedules sometimes it’s simply not possible!


          • Dan Trepanier

            Hey Tom, thanks again for your feedback.

            The current version of the Style Guide ( has about 20,000 guys using it every month, roughly 3x per week – and it’s a rough skeleton of the full concept.

            As far as the shopping, it’s obviously completely optional. There is no need to buy any products – the default window view is for commenting and discussion…the shopping is simply an add-on for those who find it useful.

            The entire concept was build in response to our user demand – we receive dozens of emails daily from our readers, they almost always ask one of three things: what can I wear to (this occasion)? how can I style (this piece in my wardrobe)? where can I buy the items (in this look)?

            As far as using content from other publishers. We are hand-selecting the providers and clearing all terms with them contractually. Since every photo is linked back to the original source, it’s a method of free advertising for them, with no downside.

            If you don’t think the concept applies to you, that’s fine, not all of our readers will use it. But if you have any other concerns or questions, please feel free to email me using the contact form on the site.

            Cheers mate!

          • Daniel F

            Haters gonna hate ! Giving $1 for all the free content i’ve received is absurdly good value for money to me. I’d suggest going home and doing a bit more research before deeming the style guide a useless annoyance Tom, it was created based on visitor demand as Dan says, I personally find it incredibly useful already in its current state.

        • Brady P

          As you’ve commented above, you follow the site… have they given you a dollars worth of content?? Whether you will use the Style Guide or not, wouldn’t you want to support the team/site?! These guys have done more for me than I can put into words and I will support them in anyway I can. Thanks again TSB

    • Keaton

      I was hoping this would be the post that I would see you finally bust out the red, white and blue Black Fleece button down polo again. I have loved that shirt since first discovering the site. Great post either way, though. Nice looks.

      • Dan Trepanier

        Funny you say that…It was a toss up between that polo and the blue/red block-stripe for look 1…

        I’ll have to work it in this summer.

        Thaks for reading brother.

    • Alex

      Hey Dan,

      What type of fabric is the cobalt blue jacket made from?

      • Dan Trepanier

        Lightweight wool.

    • Nick

      Narrative keeps on getting better.

    • Chris Reetz

      Love those loafers in Look 1! Wearin’ a tassel loafer by AE today. They work with everything.

    • Sam

      Love the post, hate that you misused “infamous.”

      Look 2 is definitely my favorite. That shirt is perfect!

    • Khalid

      So that’s how the legend begins… with Hugo Boss underestimating young Dan’s manliness.

      The leather on those Weejuns looks unusually good!

    • AJ

      Dan (or anyone else who may know),

      How does the uniqlo polo fit? I am 6-1 175 or so and usually wear a medium from jcrew, gap, h&m, etc in polos

      • Brady P

        The medium will be perfect, problem will be finding that size as most of them are gone. The Dry-fit seems to have a pretty sturdy placket as well, but dont have direct experience with em.

      • Keaton

        The uniqlo pools fit pretty slim, especially at the waist. The chest fits just like polo Ralph Lauren’s custom fit but the waist is tapered a bit more. Hope this helps.

      • John B

        Thanks to the guy who mentioned ebay!
        Being 6ft and 154lb should I go for small or medium?

        • Brady P

          Medium, they are a very nice fit and Im nearly that same height/weight

    • LouCaves

      I really liked the story behind the suit in Look 3. It was a suggestion I made for winners of the monthly giveaways.

      Not sure if that was reason for this story. But, please, continue the practice.

      Keep up the good work, TSB


      • Brady P


    • Theguybehindthelens

      Love the Uniqlo X Michael Bastian polos. I picked up the exact one from look #2 and three others before they all disappeared. I wish they would restock the collection.

    • Sean

      Any suggestions for button-down-collar polos? I never see them anywhere.

    • Kiel

      I like all the personal details in this post.

    • Brian

      Wow, awesome post. Super helpful.

      Toss up between look # 1 and 2 for me; perhaps 2 by a nose.

      Nice to hear y’all remained friends. She must have had some other “redeeming qualities.” ;-)


    • Herbert Morrison

      Dutty. Brilliant. Why is it always you? Very much enjoyed reading this post–in many ways, this is a throwback to 2-3 years ago: part instructional; part anecdotal; part inspiration; 100% gully. I’m just about to kick in for the cause–very interested to see where you’re going next. Tim O just moved to Toronto–what a nice guy Dan. This post reminds me of a fellow rapper and the greatest player today: “I’m on my King James sh*t, I’m tryna win here again–a young n%#*a tryna win here again.”

    • Brady P

      Those MBxUniqlo polos are off the charts! Might see one in a contest entry…

    • John B

      I like the backstory about the pieces on look 3!

      I want to try a polo under a jacket, but all my polos have ribbed collars and they look awful. The collar just “hides” under the lapels. In search of a button down collar polo shirt I guess!