Skip to main content
  1. Home
  2. Fashion & Style
  3. Evergreens

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.

Recommended Videos

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.

Mark D McKee
Mark cut his teeth in the men's style world when he sold suits first at box stores such as Men's Wearhouse and Jos. A. Bank…
Amberjack’s Axis sneaker delivers premium-leather comfort at a fraction of luxury sneaker pricing
Amberjack The Axis: $185 Portugal-made sneaker with full-grain leather upper, athletic EVA outsole, and arch support engineered for all-day wear.
Amberjack The Axis sneaker

This post is brought to you in paid partnership with Amberjack.

Amberjack's Axis sneaker is here and it's been quietly building a following in the dress-casual sneaker category for a good reason. At $185, it sits at a price point that genuinely undercuts the comparable luxury options. With premium build, value, and proprietary comfort tech, the Axis changes what a daily-wear shoe looks and feels like and delivers a wear experience that mass-market $100 sneakers and $400 designer pairs both struggle to replicate.

Read more
The 5 suit brands you need to know to build your first suit wardrobe: Including the first aspirational one
Building a suit wardrobe starts with the brands you can trust
Men's Wearhouse Custom

Look, starting a wardrobe is difficult. You have to decide what kind of man you want to be. What kind of message do you want to send? What kind of budget do you want to use? And how often you want to go back to the drawing board. What kind of man do you want to be? Sounds heavy. Sounds dramatic. Maybe because, in some ways, it is. So much of what people initially believe about you remains in their subconscious long after they get to know you. So what you wear is important. The message you want to send is one of being put together, attentive to details, or it is the opposite. Laid back and unbothered. The budget is also integral to the wardrobe you build. High quality comes with high prices. However, it comes with longevity, so it means you don't have to replace it as often, saving money in the long run. So, what kind of man do you want to be? Hopefully one that wears men's suits.

No matter what man, message, budget, or shopping frequency you choose, a good suit wardrobe will need to be a part of it. So, where do you go? How do you start? Here are the five brands to trust to get started. No Tom Ford, Brioni, giant fashion houses here. These are the five suits for the man starting out. And one for the man aspiring to the next step. The first four, you can grab your first quality suit for around the $1,000 mark. The aspirational one will be your first custom, so it will be a bit more.

Read more
Longines refreshes its cult-favorite central power reserve in light blue
The Swiss watch company is giving the Conquest Heritage Central Power Reserve some new dial and bracelet options.
Wristwatch, Arm, Dial

Longines has been around since 1832, which makes it one of the oldest continuously operating watchmakers on Earth — old enough to have spent decades strapped to the wrists of aviators and explorers before most brands existed. So when the Saint-Imier company, now part of the Swiss giant Swatch Group, revives something from its own archives, it's got real history to draw on. The Conquest Heritage Central Power Reserve is a good example.

The Conquest line dates to 1954 — the first Longines collection to have its name trademarked with the Swiss IP office. And in 1959, one Conquest model introduced the complication this watch is built around: a power reserve indicator planted dead center on the dial. For 2026, Longines has given the modern revival a light refresh: a new light-blue opaline dial and (for the first time on this model) a stainless-steel bracelet alongside the returning dark leather strap.

Read more