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Signature style: How to dress like fashion icon Don Draper

Let Don Draper help you master the art of the first impression and perfect The Dapper archetype

For Don Draper, an ad man of the mid-twentieth century, image was everything. He knew better than anyone that the first impression was the most important aspect of interacting with the world. Sure, it’s what’s inside that counts, but without a good first impression, few stick around to discover what’s what’s inside. Just like every bookstore is filled with bright and eye-catching covers to entice you to read the book, Draper’s image drew everyone to him.

If you want to look like The Dapper archetype, embracing the first impression is essential. More goes into perfecting the first impression than just your clothes, but starting off with your appearance gives you a leg up on drawing those around you to trust and believe in you. Here are some tips to get you started on the path of becoming The Dapper.

Don Draper
Image used with permission by copyright holder

Invest in luxury

It’s easy to give in to temptation and buy cheaper clothing to save money in the short term. The problem with that approach is that not only will you end up having to buy replacements more often, but cheaper clothing also often looks cheaper.

When shopping for formal men’s apparel such as suits, dress shirts, ties, and dress shoes, where possible, you should invest in custom or made-to-measure items. Start with the four-legged stool and then build on to that. Don’t hesitate to spend more than you normally do on your dress shoes, as they will last you for a decade or more if properly cared for.

Another place to spend more money is on the watch. There is no more classic symbol of status than a high-end watch. That doesn’t mean to go blow everything you have on a Rolex. Rather, it means that when you’re spending money, you should prioritize a luxury watch, shoes, and tailored clothing over denim, sweaters, or flashy trends. If you can fill your wardrobe with high-quality suits, shirts, and shoes and throw in a high-quality luxury watch, you’ll never fail to make a great first impression. Whether at a job interview, a formal event, or even a first date, putting forth the right image is paramount to convincing those around you that you’re in charge.

Don Draper
Image used with permission by copyright holder

Keep it simple

When trying to build a men’s fashion wardrobe or make a great first impression, one of the most common mistakes men make is trying to reinvent the wheel. Bright colors and wild patterns can certainly be eye-catching, but they can also distract from what you actually want people to focus on. If you think about the most stylish people in the public eye and on screen, they rarely wear anything more than impeccably tailored clothes in solid colors and simple patterns. Stick to solid navy, brown, and gray; if you decide to move on to patterns, basic pinstripes and checks are your best bet.

Your goal is to have all of those people focus on your face, your skills, your goals — everything except your clothing. If you think back to every season of Mad Men, Don Draper rarely wore anything but a white or light blue shirt. While your clothes are the first thing most people will notice, they should be a part of you, something that’s associated with you, not what define you. Remember that bookstore analogy about how book covers entice people to read the story? Well, if all you remember about that book is the cover and not the story, that means the writing wasn’t very good and there was just no substance. Same goes for your look.

Don Draper
Image used with permission by copyright holder

Embrace the trends

Just because your focus is on the basics doesn’t mean The Dapper doesn’t have fun. Don Draper didn’t only wear suits, nor was he limited to solids. However, when he wore something with brighter colors or patterns, the rest of his ensemble was muted. When you pick a sport coat that’s brightly colored or has an eye-catching pattern, keep your shirt and pants solid basics and let the coat do the talking.

Keeping up with men’s style trends will allow you to embrace those garments, colors, and patterns and put them on display while maintaining your sophisticated image. A word to the wise with trends: They change often, which means that purchasing new, high-quality items simply based on trends can become quite expensive. Be selective with the trends you engage in, and know which ones you should let pass you by. With your more expensive garments like suits, watches, and shoes, stick to the most classic styles and you can’t go wrong.

When combining trendy and classic, keep this rule in mind: If you have a trendy item in your ensemble, the rest should be classic. A classic solid shirt and pants should accompany a bright color or pattern on the sport coat, and you should pair a trendy shirt with a classic tie. Your trendy items should never war with each other. Follow these tips, and you can embody The Dapper archetype and always make a great first impression.

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Mark McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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