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

Sand Linen Suit

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).


  • Navy linen suit jacket ·
  • Clear frame sunglasses by Vintage ·
  • Polo shirt by Uniqlo x Michael Bastian ·
  • Watch by Montblanc Timewalker Automatic ·
  • Custom crocodile skin loafers by Scarpe di Bianco
  • · Grey lightweight suit trousers

Essential Light Gray Trouser

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.

  • Grey tortoise shades by Matsuda ·
  • Cobalt blue suit jacket ·
  • Grey stripe polo shirt by Uniqlo x Michael Bastian ·
  • Leather/suede double monkstrap shoes by Scarpe di Bianco
  • · Grey lightweight suit trousers

Essential Light Gray Trouser

Thanks, as always, for reading.

Yours in style,

Articles of Style


Photography by Alex Crawford