How to Dress Dapper

Co-authored by Dina Scherer

Last Updated: January 13, 2023

Dapper is a men’s dress style usually characterized by suits, ties, leather shoes and other chic, clothing. Dapper clothing often reflects a vintage, 60s styles, mimicking Mad Men’s Don Draper in everything from watch choice to pocket square. If you want to dress dapper, but you don’t know where to start, then learn how to transform your closet with some online tools.

Method 1

Method 1 of 3:

Planning Dapper Style

1
Request a Pinterest account if you don’t have one already. Search for “Dapper,” “Men’s Dapper” or “Dapper Style” in the search bar. Then, make a board and fill it with all the suits and accessories you like best.
- After using the site for a few weeks, you are likely to see themes in your choices. Use the site as your virtual wardrobe.
2
Go to “Dappered.com” for your style advice. On this site, you will find reviews of chic men’s clothes, advice about adopting a stylish approach to life. Fill in the blanks of dapper grooming, watches and even swimsuits by browsing their expert style sections.

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3
Find some style icons. Men’s fashion bloggers will teach you how to get all the best dapper style.^{[1]
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- A fashion blogger is likely to help you dig into the dapper era of your choice. For instance, 40s, 50s, 60s or modern approaches.
4
Purchase GQ Magazine. While the styles are likely to be too expensive to copy, you can emulate them by shopping at H&M, J Crew, Uniqlo, Topman and ASOS.

Method 2

Method 2 of 3:

Choosing Your Wardrobe

1
Go shopping in your own wardrobe. First, take out suits and shirts that fit your style but might be too big. Most men buy one size too big.
2
Find a great tailor. Look in your local newspaper coupons, yellow pages and online listings for a local tailor who can adjust your suit coats, pants and shirts to fit you perfectly. If you want to save money, look for an independent tailor, rather than one in a shop, since they are likely to give you a deal for tailoring a lot of clothes.
3
Start with the shoes. If you don’t own a pair of oxfords, wingtips, derby shoes or loafers, buy a pair. Choose leather, weatherproof them and shine them regularly, and they should last you for years.^{[2]
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- For a sportier look, try military inspired Chukka boots.
- Popular brands include Clark’s, Steve Madden and Sperry Top Sider.
- Look for a deal on eBay, Amazon or Overstock.
4
Move to jeans. You can look dapper in jeans, but start with selvedge slim fit jeans in a dark wash. Get them tailored if they come close to touching the ground.
5
Buy a suit if you can’t get the one you already own tailored. Look for sales on slim fit suits and Brooks Brothers, Macy's or even Men’s Warehouse. Some department stores even include tailoring for no extra cost, although you usually have to pay for the service.
6
Collect blazers and suit coats. Dapper style is versatile; so that you can wear a vintage blazer with jeans, suit pants, slacks and a shirt. Shop at J Crew or look through vintage and thrift stores to find slim fit blazers or those you can tailor cheaply.
7
Buy a good collection of button up shirts. Trade in your t-shirts for colored, white, plaid, patterned and striped shirts. Look for sales at The Gap, J Crew, Urban Outfitters and department stores, and pick them up whenever you can.
- Make sure the shirt sleeves are long enough. When you wear a shirt and a suit coat, approximately one-fourth inch (0.6cm) of your shirt cuff should be showing through the bottom of the coat.
- When choosing shirt colors, make sure they match your suit and ties. It's usually a good idea to choose colors that are part of a monochromatic family. For instance, for a navy suit, a light blue shirt and a tie with blue accents is usually a good combination. When colors are complimentary, the look feels more polished and put together.

Method 3

Method 3 of 3:

Accessorizing Dapper Style

1
Buy a good belt that matches your shoes. Wear it with jeans, suits and slacks. It can be military style, with a good buckle or leather. Choose brown or black shades.
- When buying a belt, you need one that is two sizes above your waist size. If you have a size 30 waist, you need a size 32 belt. Military belts are adjustable.
2
Use pocket squares. Fold it in half twice and then place it in your pocket with one-fourth inch showing. Match the pocket square to a color in your shirt or your tie.
- You can also match the pocket square to the color of the lining of your suit.
3
Splurge on socks. Bright and men’s patterned socks show a little style and color. However, they only peak out occasionally. They show full commitment to a dapper style.
4
Wear cufflinks to dress up more. Buy one shirt that requires cufflinks, to wear at parties, weddings and other events. Purchase metal cufflinks.
5
Buy a watch. Although you may use your cell phone to check the time, a round-faced watch with hands is essential for a dapper outfit. Choose an explorer watch or any nice watch with a leather or metal band.
6
Master the necktie. You don’t need to wear one every day, but a well-worn four-in hand or Windsor tie is a good touch. Break out the bow tie on special occasions and garden parties.
- There are some different types of ties and details that can be larger or smaller, depending on your body size. For instance, if you're tall and broad, a skinny tie might not look as flattering. On the other hand, this smaller accessory will be good if you're more slimmer built.

Community Q&A

Question

How do you feel about suit vests? What can they be paired with, casually and formally?

Community Answer

Vests are a great option if you are looking for a little spice to your wardrobe. The great thing about them? They are incredibly versatile. You can either pair them up with dress pants and shoes (with a tie) or you can pull off a more rugged look with jeans.
Question

Is a golf shirt is a good option too?

Community Answer

Yes, it is, for more casual outings, especially if you pair it with canvas slacks or simple dark wash straight leg jeans that don't have obvious distressing.
Question

Where can I start in a way that won't break my small budget? Maybe I should start off with a small piece first?

Community Answer

For starters, get a well-cut white shirt that fits you perfectly and a nice pair of everyday lace-up shoes from leather or faux leather. Make sure you also get simple black socks for the shoes. It's a small and subtle change but it'll make a difference.