Manly Mondays: Evening Wear

Up until now I’ve spared you from dress shirts, ties, and suits. But now its time to man up and look fantastic for a night out. Finding a nice dinner jacket and pants can make it a breeze to get dressed for a fancy night out.

Shirt and Cufflinks

French cuff shirts are the only thing to wear under a dinner jacket. Cufflinks look better then a normal buttoned cuff and and are one of my favorite accessories.  Cufflinks can be sleek and simple or creative and whimsical, and often have a matching tie clip.  Cufflinks can be found everywhere from Goodwill to antique malls to high end vintage shops to Etsy.

Like a lot of other mens clothes, shirts were often tailored to fit the wearer, so finding a vintage one is difficult. I ended up getting one at Nordstrom for my wedding and had it tailored.

When you go out to buy a new shirt, suck it up and ask a sales associate to help. Shirts are fitted based on your neck size, shoulder width and how long you want the sleeves to be. If you already have your jacket, bring it along when you shop for your shirt so you can get the right sleeve length.

Because shirts are measured at the neck and shoulders, they often run to large everywhere else to accommodate larger body sizes. The downside to this is there can often be a lot of fabric left over when you are done tucking you shirt in. Without tailoring, my shirt would resemble a small tent hanging from my neck. Get your shirt tailored, it costs less then $20 and you can often get it done when you buy your shirt.


Your jacket is arguably the most important piece of your ensemble, it sets the tone for your entire outfit so its important to get it right. Fitting at the shoulders is essential, as almost anything else can be tailored. A quick tip to check shoulder size is to lean against a wall, if the shoulder of your jacket touches the wall before your arm the jacket is to big. Getting things tailored can be expensive, but fortunately you can find dress pants and dinner jackets just about everywhere and they tend to be cheap. I just picked up a 1930s dinner jacket with matching pants for $25, so my total cost after tailoring the set shouldn’t be too much.

Pay attention to the width of your lapels, they should be proportional to your  shoulder width, if you have larger shoulders don’t pick a huge lapel because it will make your shoulders look even broader. Thin lapels will also make your narrow shoulders look small and wearing fat lapels with narrow shoulders will be overbearing. Start at around a two inch lapel and go from there. Your lapel width will also determine how wide your tie can be. Try to keep your tie width within a 1/2 inch of your lapels.


Ties are a staple of vintage shops and thrift stores and since almost no one ever looks you can afford to be picky. Your tie is the central visual piece of your outfit so its important to pick something that looks good and stands out. Be unique with your choice of ties.  It’s a great way to reflect your personal tastes and style. Just remember to keep the width of your tie around the width of your lapels and make sure the style matches.

If you don’t know how to tie a tie, start by learning the Four-In-Hand knot. It’s the easiest knot to learn and will get you through about any situation. If you want a good link this site has a few different kinds of knots if you are looking for something different.

Tie width and design vary a lot depending on the decade.  The 1940s saw wide ties with some fabulous and, at times, flamboyant designs.  The 1950s started with the wider ties of the 40s, but as the decade went on, they became very narrow and by the 1960s, one inch ties were all the rage with more subtle designs.


Black pants and nicely shined black shoes compliment just about any tie and jacket. Pants should either be the same color as your jacket or a solid color that compliments your jacket.  Navy jacket? Black pants.  Brown and tan fleck jacket? Brown or tan pants.   Additionally, you want to be careful with where your “break” is. The break is how much fabric gathers at your shoes when you are standing. If your pants are too long it will show because to much fabric will gather. If your pants are too short you will show some ankle and look like you don’t know how to dress yourself. Effortless Gent has a great guide on how to get the right break.

Finding Everything

Check out your local Goodwill. Many resale stores such as Buffalo Exchange often don’t take mens formal wear because they think they can’t sell it. If you find something at a thrift store, you will probably have enough money leftover to get it tailored. Look for a simple style that will go with just about everything.

Often, the menswear section at vintage shops is small, however there are a handful that tend to specialize in menswear. In Portland we have Hollywood Vintage and Avalon. You’ll find a lot of good stuff in one place, but the price goes way up. A jacket and pants might cost you $70-$150.

When you shop, make sure you know your shoulder measurement (the width from tip to tip on your shoulders) as well as your neck, waist and inseam measurements.

To get you started here is an Etsy treasury of vintage cufflinks. They range from about $10-$200 so you should find something in your price range.

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