11 Essential Rules To Dressing Like An Adult

How to dress like a confident, in-the-know guy

Your driver’s license gives away your age. Don’t let your clothes do the same. Now is the time to start showing off the older, wiser, sophisticated man you are—starting with these essentials.

1. Find A Suit That Fits

A little boy wearing a suit for the first time is cute. A grown man trying to pull off an ill-fitting rig is anything but.

You know the drill by now, so wear a suit that shows it. 

2. Invest In A Great Pair Of Jeans

Finding that perfect pair of well-fitting jeans is worth the steep price tag. Look for three must-have qualities—a slim fit, dark wash, and sturdy construction—and you’ll be able to wear your jeans just about anywhere.

3. Upgrade Your Outerwear

You spend most of the winter months in a coat, so give it the attention it deserves.

Leave ill-fitting puffy coats to the amateurs—you need a sharp overcoat that slims your body with room for layering, so you’ll look sharp whether you’re wearing a suit underneath or just a pair of weekend “no need to put on clothes to get the morning paper” pajamas.

4. Buy Nice Shoes To Wear With Jeans

Rule No. 1 for upping your shoe game: Leave the athletic shoes at the gym. Instead, reach for a pair of leather chukka boots that pack style and comfort.

5. Know When Shorts Are Appropriate 

Shorts shouldn’t be banned from a gentlemen’s closet. Just know when to wear them.

You’ve got until Memorial Day to add fitted shorts that hit above the knee to your wardrobe. They’ll cut back on any hint of sloppiness to keep you looking sharp.

6. Upgrade Your Tees 

Sure, there’s an emotional tie to each of your old fraternity tees, but they’re holding back your style. Make room in your dresser for a handful of well-made, solid T-shirts in neutrals like black, gray, and olive. 

7. Match Patterns With Skill

As a general rule, aim to match patterns that contrast in size. That means pairing a fine gingham shirt with a tie in a larger plaid.

The resulting balance doesn’t clash and shows you’ve put some thought into your look.

8. Pay Attention To The Little Things

Look at a guy with enviable style and you’ll notice what sets him apart often comes down to the accessories. Invest in a sturdy tie bar, cufflinks, and a versatile white pocket square.

Rest assured: People will notice. 

9. Find A Leather Bag

Toss out your logoed nylon messenger bag. It’s a switch your co-workers—especially your boss—will notice.

Replace it with a simple leather briefcase that’s label-free, so you can take all the style credit. 

10. Press Your Dress Shirts

You’re not in high school anymore, so it’s up to you to make sure your shirts are pressed and wrinkle free.

Make it easy by choosing a fabric with wrinkle resistance built right in.

11. Refresh Your Jewelry

When you put away the cap and gown, it’s time to retire anything that labels you as a student. This includes pooka shells, string bracelets, dog tags, and anything resembling a piercing.

Leather bracelets, like this from Giles & Brother, or a nice watch offer a solid replacement.

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