(Author) Jeffrey Westbrook/Studio D; (Clothes) J. Muckle

The author and his $953.57 worth of new clothing. First row, from left: Jackets by Uniqlo, Muji, and Gap. Second row, from left: Alpha khakis by Dockers; jeans by Mavi. Third row, from left: Sweaters by Uniqlo and H&M; shirt by Camicissima; jeans by Uniqlo. Fourth row: Shirts by Camicissima; pullover by Gap.

Published in the December 2011 issue, on sale now.

There's a British man man in my closet. Nick Sullivan, Esquire's fashion director, a longtime neighbor, and the kind of man who occasionally changes into a tuxedo before leaving the office at night, was thumbing his way through my shirts, sweaters, and pants while I stood by quietly, feeling very bad about myself.

It's my own fault. I bought those shirts, like the ugly brown-gingham cowboy shirt with pearl snaps that can't even be hidden under a sweater (the snaps look like nipples) and the orange-and-blue-striped button-down that's only a bow tie and a better voice away from getting me into a barbershop quartet. Also, I invited Nick here. I asked for his help, because I really needed it.

There was a time when I thought I dressed well. I even got compliments. But that was in D.C., where all you really have to do to outdress your coworkers is tuck in your shirt. Still, feeling welldressed felt good. But then I moved to New York. Suddenly, the only part of my wardrobe I felt confident in was the sweaters I borrowed from my gay (and very stylish) roommate when he went out of town. I was in a rut, and seven years later, it's only gotten deeper. At 33 years old, I dress like a high school science teacher. And not even the cool one.

My plan was simple. I would commit to spending $1,000 of my own money under Nick's supervision — an amount that wouldn't clean me out but would be enough to make a noticeable difference in my wardrobe. As his protégé, I'd soak up everything Nick could teach me in the hope of eventually doing it myself. As my coach, Nick would share the knowledge and skills he's accrued over two decades in the fashion business, all while making sweeping decrees, helpful suggestions, and secretly enjoying having someone take notes as he talks.

The first step of rebuilding a wardrobe is to figure out what, exactly, needs to be rebuilt. Hence, the cleaning out of my closet. Of my more than 50 long-sleeved oxfords — Nick said I had even more dress shirts than he did — I got rid of nearly 30. Shirts that didn't fit or had stains or just weren't appealing to people with taste or decent eyesight. As we went through each one, Nick said either "okay" or absolutely nothing, grimacing a bit as he placed it in the "no" pile. When we got to my pants, it was even worse. Ten-year-old wide-leg Gap khakis, some mistake in a plaid flannel — I dropped seven pairs there. "Modern pants have a taper," Nick explained, and then pointed to what he was wearing: a pair of hunter-green khakis that, I couldn't deny, looked a lot better on him than any pants have ever looked on me. Plus, he said, the narrower your pant leg, the dressier the shoe you can wear with it. "You can finally wear some of these nice shoes you've got in here," he said. "When it's a little colder, I'd definitely bring out those boots," he continued, gesturing to a pair I hadn't had the guts to wear in years.

Back at the office, we devised a plan of attack: I needed three to four dress shirts, a blazer, chinos, jeans, and a couple of sweaters to set my closet in order. The biggest chunk of my budget would go toward the blazer, an investment that Nick said "bridges any outfit." Fit and tailoring, he explained, make an outfit look dressy. If a casual blazer is made well, it can look elegant, and if it's properly cut, it can look like it's much more expensive than it really is.

The following Wednesday, right after lunch, we headed out to SoHo, where we could walk between stores and battle the throngs of Japanese tourists in our way. My hopes were high. I figured with Nick leading the way, I'd be coming home with more bags than I could carry. At J. Crew, Nick walked right to the suiting section. He had a focus, a game plan, that I never have in stores, walking directly to what he wants instead of aimlessly flipping through the racks. And he takes advantage of salespeople: Whereas I normally stay away from them, hoping to avoid the guilt that will come when I inevitably don't buy something, Nick goes right to them, explains what he's looking for, and has them bring clothes to him. He asked for a suit coat that he'd seen online called the Ludlow. It's cut perfectly for someone with a slim build (which, at six feet and only 155 pounds, it's safe to say I have). The jacket looked great — and fit perfectly — but they didn't have it in navy. I was discouraged, but not Nick. We'd just look online, he said. One of the best recent developments in shopping, he said, is that you can try on things in the store and then find them much cheaper online.

We had similar luck at Club Monaco, where Nick had me try on a few jackets that I never would have picked up on my own. They just seemed too dressy and too ... what's the word? ... European. There wasn't anything we liked enough to buy, so we continued on to Bloomingdale's, where Nick schooled me in the art of picking out a shirt. The collar's important — the farther the stitching is from the edge of the collar, the better the craftsmanship. The first one I tried on, around $100, was more than we wanted to spend. Same goes for the slim-fit Dockers he wanted me to buy: At $120 each, they were too pricey and came only in neon blue and marigold. We wrapped up the first day and headed back to the office empty-handed. Disappointing, maybe, but it was a relief to see that even a guy like Nick doesn't always find exactly what he wants. But he keeps trying.

This called for reinforcements: Nic Screws, Esquire's market editor. While Nick speaks with a suave British accent, Nic called me "Boo" and told me when things were "major" and "everything" and, worst of all, "not cute." But the woman knows her stuff, and so we headed out again to stores I'd never even heard of. First stop was Camicissima, an Italian company that uses high-quality Egyptian cotton but saves money by having its shirts constructed in China. They come in two cuts, regular and slim, and only one sleeve length, which luckily was just right for me. I tried on the slim first. The fit was great everywhere but my chest, where it was tight enough to pucker the material a little. "Look at you, all beefy," Nic said, which I pretended not to be flattered by. "Try on the regular." The regular was huge, so we went back to the slim and decided I'd focus a little less on weights and more on cardio. For $125, we got four shirts. We stuck mostly to blues — stripes, a check, and a faint plaid pattern — except for a purple microstripe that Nic had to work very hard to convince me to buy. "Trust," was all she said. After three decades of not being able to buy a properly fitted shirt for myself, Nic was able to do it in 30 minutes. I'd been going to the wrong stores, and I'd had no idea what it actually meant for a shirt to fit. The armholes should be high, the chest should be taut (maybe not this taut), and the sides should billow only as much as your actual sides do.

We needed jeans, so we headed to Mavi. Jeans were the only really contentious issue we faced, and not just because I got uncomfortable every time Nic said, "Show me the back." The problem was fit. I didn't mind a taper, but she had me trying on jeans that felt like leggings. Each pair I put on felt wrapped around me like a half-hearted boa constrictor. I bought them anyway — she is a woman, and she knows men's style — and once we left the store and I started to notice the cut of other men's jeans, I realized Nic was right. The more narrow and fitted the jeans, the better most men looked. There is such a thing as too narrow, but as long as I could breathe and bend my knees enough to sit down, I was in the clear.

The all-important blazer remained at large. We headed to Uniqlo, where our goal was to check out Jil Sanders's line, +J, and to get a couple of inexpensive staples, like a gray cashmere sweater and another pair of jeans. We'd already found a casual blazer from Muji — a Japanese store that's relatively new to the States — so we needed something dressier. As Nick had said, the more tailored the cut, the dressier the blazer, and +J was a great way to find a high-end fit at a mass-market price. I struggled with the sizing a little bit — the small too small, the medium too big — but I learned that buying clothes is about making choices. Nothing is ever going to fit perfectly, so I had to prioritize and pick my battles.

I can't emphasize enough the value in having a coach. Or two coaches, really, each with their own way of reassuring me when I was frustrated, correcting me when I was wrong, and steering me toward things I wouldn't normally even have looked at. Like those jeans. Or the plum-colored sweater that I found myself trying on in H&M's fitting room. When Nic pulled it off the shelf, I shuddered. She insisted, and I put it on. "Trust," she said. Trust.

In all, I spent seven hours in stores with Nick and Nic. I bought two new pairs of jeans, three chinos, a few sweaters, three blazers, and four dress shirts for $953.57. While I'm not at the point where I think I can do as well on my own, I won't be as intimidated the next time I go shopping. I'll work with the salespeople gladly. I'll go to another store if I don't find what I like. I'll take my time figuring out the fit. And I won't give up quite so easily.

Mix, Match, Repeat

Five office-ready combinations of the author's recent purchases

This content is created and maintained by a third party, and imported onto this page to help users provide their email addresses. You may be able to find more information about this and similar content at piano.io