IN CHARACTER, IN MANNER, IN STYLE, IN ALL THINGS, THE SUPEREME EXCELLENCE IS SIMPLICITY. – HENRY WADSWORTH LONGFELLOW 

What’s old is new again. It’s true…just like almost everything else in life, the classics in menswear always make a return (or sometimes–never leave). A solid white dress-shirt, polka dot tie, windowpane sportcoat, and tasseled loafers are 4 pieces of this look that have a past deeply rooted in menswear history. First, the quintessential white dress-shirt you can NEVER have too many of. Perhaps you’re familiar with the terms “white  collar” and “blue collar”. These terms were created when washing machines didn’t exist and white shirts were a challenge to keep clean. For that reason, a white  collar described a man who worked in an office, and a blue collar represented someone belonging to the working class. Next, we have the polka dot tie, which originated from England during the late 19th century. Back then, polka dots took the form of bow-ties, scarves, and kerchiefs. The polka dot trend in the U.S. arguably started when Disney first introduced Minnie  Mouse in 1928 with a red  polka dot dress and matching bow. There’s definitely a nostalgia associated with the polka dot print too, I always think of vintage clothing from the JFK era. Another pattern born in the late 19th century and popular again in the 1970s is the windowpane check. As you can see from my sport coat, the name comes from the window-like square pattern formed by two perpendicular pinstripes. It’s been considered to be ‘out of style’ for years, but the windowpane pattern has been popping up again at fashion weeks (cc: Michael Bastian) , bespoke tailors, and at Pitti Uomo with no signs of slowing down. Lastly, we have the tassel loafer which became popular post WWII by a custom request from a debonair actor by the name of Paul Lukas. By simply adding two small tassels, a loafer is transformed into an elegant piece of footwear reminiscent of old Hollywood glamour.

Styling Tips

White Dress-shirt:

• Let’s start with the sizing basics, because there’re more to buying shirts than small, medium, or large. First, you’ll want to measure the circumference of your neck to figure your neck size.  Do this over your Adam’s apple where the shirt collar would normally be and make sure to have a little extra room to fit 1 finger comfortably. American sizes are in inches and you’ll have to ask Siri to convert inches to centimeters for your European size. For example, I am a size 15in or the equivalent 38cm. Next you’ll need to measure your arm length and this is a little hard to explain so feel free to Youtube it as well. Start by placing one hand on your hip, then ask your friend to start one end of the measuring tape at the base & center of the back of your neck, run it over your shoulder, to your elbow, and right down to your wrist.
• Trim the fat! This is a huge epidemic that is affecting so many men in this country. There are few things in life I hate more than seeing a guy in a ballooning shirt with enough room to fit their families inside. It doesn’t matter if you’re a cut athlete with a six-pack or a couch potato…buy a shirt that fits closely to your torso. The extra fabric is unflattering and only exaggerates your size if you have a gut.
• Match the size of your collar to the size of your lapel. If you’re suit  jacket has a wide lapel, it’s going to look silly if you wear skinny collar and/or tie.
• Don’t have inches of shirt showing at the cuff. There should only be about 1/2–3/4 inch of cuff showing past your suit jacket…that’s it.
• Another huge pet peeve of mine is seeing a guy at the bar with an untucked dress-shirt. They’re intentionally made longer for the purpose of tucking them in! Keeping a shirt untucked with a blazer doesn’t give you swag points, it just makes you look sloppy. Pull it together and keep things tucked and in place.
• Speaking of keeping things in place, wear an undershirt too. My personal favorite is the Tommy John undershirt made of a comfortable cotton blend. They’re fitted but not restrictive and stay tucked in with a longer length design that hugs your torso and hips, which in turn, gives you a streamlined and clean look. An undershirt is also a great way to promote the longeivty of your dress-shirt, acting as a defensive barrier from your body sweat and deodorant residue.
• Get collar stays to stop your collars from curling up and lying flat. I recommend these magnetic ones from Würkin Stiffs, you might recognize them from shark tank.

Polk Dot Tie: 

• Don’t be afraid of pairing a miniature polka dot tie with a patterned shirt. They’re super versatile and can be worn with almost any shirt pattern.
• Enter the polka dot world by choosing a tie that’s either navy, burgundy, or a graphite. I’m thinking versatility again.
• Match the width of your tie to the width of your lapel, just like your shirt collar…everything should be in sync. Generally speaking, keep it between 2-1/4 in– 2-3/4 in at the widest point.
• The tip of your tie should hit the top of your belt line (I know…mine is a bit higher in the picture below and that’s because I wanted to show detail).

Windowpane Sportcoat

• The key is to keep things balanced here. If you have a large windowpane print going on, you want to balance it out with a smaller patterned shirt or a solid shirt and patterned tie. If you’re new to pattern mixing, it’s easiest to work with the 2/3 rule. This is where two out of the three components (suit, tie, shirt) are patterned and one is a solid.
• FIT IS EVERYTHING. Whether it’s a $100 suit or $5000 suit, if it doesn’t fit it’s going to look cheap. The many factors that go into a suit fitting can be it’s own feature on the blog, so for now I’m going to out source to The GQ Guide to Suits. Check it out for some helpful tips for buying the perfect suit on any kind of budget.

Tassel Loafer

• I know most of you are going to think the tassel loafer is a dainty piece of footwear and that’s unfortunate because it really is a versatile shoe that can be worn casually with jeans or formally with a suit…you just need to man up and wear it with some confidence.
• Make sure it looks substantial, clean, and modern. Do so by choosing a style that has a longer vamp (part that covers the top of your foot and toes) and a solid heel.
• I would enter the tassel loafer game by choosing a chocolate brown leather like mine or a suede in navy or shade of brown/beige.

Sportcoat: Ralph Lauren Black Label | Shirt: Banana  Republic | Tie: All Saints | Tie Bar & Pocket Square: The Tie Bar

Belt: Burberry | Denim: A.P.C. | Shoes: To Boot New York

Location: Lincoln Park/ Chicago

Photography: Nancy Rahman