“I wear a tie occasionally—but not if I don’t have to.” Not exactly endearing first words from my fiancé, Adam, to Tony Wright, an assistant manager at the Tie Bar. If Wright was offended, he didn’t show it, likely because the Chicago-based company has expanded its offerings beyond its bread-and-butter product to everything from pocket squares to dress shirts. Last month, it added made-to-measure suits and style services to the list, including the Closet Clean, where a $250 minimum purchase brings a stylist to your home to evaluate what’s stocked in your closet.

The service starts with an online style questionnaire (What’s your favorite color? Where do you normally shop? Thoughts on skinny ties?). Then, you purchase a $250 gift card to the Tie Bar, which you can spend on items the stylist brings to the session or to use for online purchases based on suggestions during the cleanout.

My fiancé volunteered his disorganized, rarely updated closet to be scrutinized. We both were expecting a massive closet overhaul that’d end with a car full of donations to Goodwill. In reality, though, the Closet Clean is more of a one-on-one style consultation. “It’s about seeing what you have in your closet and saying, ‘This tie will work with these five shirts that you already have,’ or, ‘You’re missing this kind of shirt,’” Wright says.

Not exactly the Marie Kondo cleanse we had in mind—but helpful nonetheless for Adam, a lawyer who sticks to a steady rotation of dress-shirt-and-pant combinations, with the occasional suit thrown in.

Here, Wright offers five guidelines for updating your wardrobe.

1. Slim down your conservative ties.

If you’re still rocking ties from the early aughts, it’s time for an update. The width of your tie should be proportional to the lapels on your suit, which likely are slimmer than they were back then. Wright suggests taking the end of the tie and placing it against the width of the suit’s lapel. “It should be even—or even slightly smaller—than the lapel,” he says. Worried about going too slim too fast? Start by adding a few 3-inch-wide ties to your rotation and work your way down to 2.5-inch widths when you’re ready.

2. Know what to toss.

After a little nudging and insisting no feelings would be hurt, Wright helped identify which pieces had to go. Among the styles he suggests tossing (or donating): shirts with yellowing around the collar, shorts that go past the knee, Two and a Half Men-style camp shirts, and non-solid T-shirts. Beyond that, pull out things you don’t wear or heed Wright’s hack: “Last spring, I faced all of my hangers the wrong direction,” Wright says. “If I wore the item, I’d flip the hanger back around. If I didn’t wear it, it stayed that way. And if I didn’t wear it all season, I threw it away so I don’t stuff my closet with crap I don’t wear.”

3. Choose your summer ties based on material.

Silk ties technically work year-round, but summer presents more interesting options, such as cotton, linen, and knit. They’re inherently more casual yet still dressy enough to wear to an outdoor wedding or to the non-stuffy office. The hardest of the bunch are knit ties—Adam admitted being intimidated by them—but if you’re ready for the challenge, choose a width of 2 inches maximum. “Anything wider looks like you’re wearing a scarf,” Wright says.

4. Accessorize beyond the tie.

If there were ever a time to play with bold accessories, summer is it. But don’t stop at the punchy patterned tie. Pick out the tie’s secondary color and let that guide you when choosing other accessories. “This [yellow tie] has a light blue dot, so if you’re going to do a white shirt with this you can do a light blue pocket square,” Wright says. Same goes for socks. Consider the old rule of choosing a sock color that matches your pants officially dead.

5. Freshen up the basic white dress shirt.

Adam had adopted a conservative formula for getting dressed in a suit: He always wears a solid white shirt with a solid navy or gray suit so he doesn’t have to think about matching. Put that on repeat for a few years, and though it’s foolproof, it’s boring. For a more interesting update, swap the white dress shirt for light pink, which Wright says is one of the Tie Bar’s bestsellers. Treat it like it’s white—it’s just as versatile, Wright says.