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.
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.
9. Find a leather bag
Toss out your logged 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.
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.