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. The first step: Learn the basics of How to Buy the Perfect-Fitting Jacket.
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. And keep them looking new with these tips on The Cheapest Way to Upgrade Your Shoes.
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. Try these from Alternative Apparel.
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. Here are 6 More Details to Make Her Notice You.
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, or use these 4 Steps to Wrinkle-Free Shirts.
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.