My buddy Jake texted me last weekend sometime around 2AM. Completely rattled. “Dude. I just got promoted.
I have a meeting with the board next week. Everything in my closet is ripped from Target’s clearance rack. Do I just burn it all and start over?” I should have known he was coming to me for advice when he said he was dressing like Tyler Durden.
Everyone goes through these phases where you open your closet and wonder how your pants are stopping you from getting what you want in life. I told Jake he didn’t have to burn his whole wardrobe and spend $3,000 at Banana Republic.
I’ve seen far too many guys go on these shopping frenzies and come out the other side hundreds of dollars in debt from clothes they never really feel comfortable in.
That’s one of my biggest pet peeves about the menswear hobby. So many guys are taught how to break in a new wardrobe instead of how to upgrade what they already own. When I picked Jake up for coffee the next morning he was a wreck. “I’ve been reading articles about ‘executive presence’ all night,” he said rubbing his eyes. “One article said the only suits I should own are navy and gray because they’re the most powerful colors. ‘Blue is calming,’ said one expert. ‘Gray symbolizes confidence,’ he helpfully added.
Another website said I need a $2000 watch because nobody takes you seriously as a leader if you’re not wearing an expensive watch.” This is what happens when civilians go down the menswear hole. You learn there are professional “experts” out there just waiting to tell you to spend money. The first thing I had Jake do was empty out his entire closet.
Before you go buying new stuff you have to know what you’re working with. As it turned out, he had some decent building blocks to work from. Two navy suits (one of them was actually really nice), a charcoal suit from his brother’s wedding, some basic white and light blue dress shirts that weren’t too bad, a handful of ties, and a pair of black leather dress shoes.
Nothing groundbreaking, but definitely not a thousand-dollar Netflix prop closet either. 
The biggest problem with Jake’s wardrobe wasn’t what he owned, it was that it all looked terrible on him. First off, none of his clothes fit him correctly. He had lost about twenty pounds over the past year but hadn’t bothered replacing his suits.
They were hanging off of him and looked awkwardly large in the shoulders and chest. His dress shirts looked slept in. His shoes … let’s just say you wouldn’t want to wear shoes that looked as beat up as his did. “What you need,” I told him, “is a good tailor.
Not new clothes. A good tailor.” If I had to pick one thing that’s made the biggest difference in my clothes looking better it’s taking everything to get altered. A well tailored suit can make even a $300 suit look more expensive than that $1500 suit that wasn’t fitted to your body.
I found this awesome tailor named Ricardo down by the waterfront and took one of my cheaper suits in to have adjusted. People complimented me on how nice that jacket looked so much I actually believed they thought it was an expensive jacket. Fast forward a few days and Jake and I are sitting in Ricardo’s office waiting for him to finish work on two suits. “Everything’s too big on him,” Ricardo told me. “Jacket too long, pants too baggy, take in the shoulders a bit but the rest…” He pinched the fabric on Jake’s suit jacket and continued.
Two hours and $160 later Jake had dropped off two suits to be altered and picked up Monday. Proper tailoring was going to cost more than finding cheap suits at Target, but it’d be way less expensive than buying new suits that fit. Best decision my friend ever made. 
While Jake’s clothes were being fitted to his body nicely, I showed him some closet hacks that could make boring clothing look a lot more expensive in no time.
Accessories are honestly the easiest way to elevate your wardrobe. It’s the simplest upgrade you can make that immediately improves the look of everything you own. “Text me a picture of your ties,” I said to Jake that night. He sent me back a picture of his tie collection.
What I didn’t show him were the faces his friends made when he pulled out his ties to show them. All polyester. All ugly Christmas tree patterns.
All sad. The next day we went to J Crew’s SALE SECTION and picked up three silk ties that weren’t boring. One navy knit tie, one burgundy tie with tiny dots, and this beautiful olive tie that looked WAY more expensive than the $25 J Crew was charging for it.
While we were shopping I also strong armed him into buying a few pocket squares. “You don’t need to learn crazy folds,” I told him. “Just stuff it in your pocket so some of it shows. It’s an easy way to add personality to a plain outfit that doesn’t cost any extra money.” Now it was time to work with what he had. Luckily for Jake his white and light blue dress shirts were fine.
They weren’t fancy but clean white and blue oxford shirts are classic for a reason. They go with everything and look professional. The only problem was they looked dingy.
We dropped his shirts off at the good dry cleaner. You know the one I’m talking about. The one that costs twice as much but makes your clothes actually feel new when you get them back.
Sure, we spent $25 to clean his shirts. But his shirts looked terrific. Actually crisp white shirts that didn’t look worn out. 
Next up were his shoes.
Thankfully I’m one of those dudes that always has a shoe care kit in my backpack. So I gave him a mini lesson on keeping his shoes looking sharp. We went with a basic black shoe polish since those were the shoes he wore most often.
They weren’t high end shoes but they didn’t look cheap after we buffed them out. “Do this every week,” I told him. “Shoes should never look like you don’t care about them.” You’d be surprised how much of a difference a $6 can of shoe polish can make. “Wait, so I don’t need to replace any of my clothes? I just make what I own look more put together?” Ohhh Jake. You’re getting it.
That’s exactly what I’m talking about. Instead of replacing your entire wardrobe you should ask yourself what you can do to each piece to make it look intentional. For Jake his suits and dress shirts were good after some tailoring and cleaning.
His new ties and taking care of his shoes fixed 90% of his problems. The only thing that was actually worn out were his belt. 
His black leather belt was cracked and worn. The buckle looked like it had been through a war.
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We replaced it with a simple black leather belt for $50 and suddenly his whole outfit clicked. Last thing was his work bag. It was this sad canvas laptop messenger bag that gave off major “I don’t know what I’m doing with my life” vibes.
But Jake needed a bag he could bring to work. He didn’t have the money for a quality leather bag, so we settled on this used vintage leather bag I scored at downtown. After about an hour of digging through bins of old junk we found this brown leather messenger bag that retailed for $200 but we got for $75.
Slapped some leather conditioner on it to soften it up and bam. It was professional without trying too hard. Sunday morning rolled around and Jake was looking and feeling a lot better about the whole ordeal.
We had managed to fix the major issues without draining his bank account and he looked awesome. But there was one more lesson I had to teach him. The small things that will really help you up your style game. “How do you tie your shoes?” He laughed at me. “What?” I replied. “Little things.
You always sling your pants pockets so hard they look uneven. Learn how to sit properly, or at least not droop in your chair. When was the last time you got a haircut?” He shrugged. “Like a month ago.” Wrong answer.
I drove him to the barbershop that Sunday. Nothing fancy. We just cleaned him up a bit so he looked a little more professional. “Every four weeks,” I told him. “No excuses.” 
Before he knew it Monday morning had rolled around.
He even took me a pic of his new look. The navy suit fit him perfectly now thanks to the alterations. The white dress shirt looked great against it since we got it professionally cleaned.
His new burgundy tie and white pocket square broke up the solid colors and added some interest without being distracting. His black dress shoes looked nearly new since we polished them. Hell, even his new belt and vintage bag gave him some personality.
He wasn’t rocking Balenciaga shoes or anything, but he looked put together. Confident. And most importantly… he felt that way too. “When do you get off work?” His boss texted him that afternoon. “The CEO stopped our meeting to ask where he could buy that tie.” He looked so good that guys higher up than his immediately noticed. “DUDE YOU’RE welcome.” As I was helping Jake with his style crisis I started thinking back to when I moved to Portland and didn’t know how to dress for the creative scene.
I was certain I needed to start from scratch and reinvent how I looked. I bought trendy clothing that I never ended up wearing because it didn’t fit who I was. The biggest lesson I learned was that I should’ve just started with who I was and upgraded it.
Getting my favorite blue jeans hemmed so they didn’t drag on the ground, spending a little more on higher quality shirts I knew I’d wear all the time, and finding accessories that I loved ( vintage watches for me) that helped take my outfits to the next level. 
The best style upgrade I did was actually free. I took an entire weekend and tried on every single piece of clothing I owned. I was brutal with myself about what I kept and what I needed to get rid of.
Shirt was too tight? Donate. Pants were too long?
Donate. Didn’t go with anything in my wardrobe? Donate.
When I was done I probably donated about 4 huge bags of clothes. I felt amazing knowing I only wore clothes that looked good on me and that I enjoyed wearing. Sure I had less clothes than I started with but everything I owned worked with everything else.
That right there is a game changer. My dad used to give me all these style tips when I was in high school. One of the best ones was when I showed him I thought rolling up my sleeves was cool. “If you gotta roll your sleeves, roll them like you mean it,” he said as he demonstrated the proper way to roll up a shirt.
Half aggressive half smart ass I asked why it mattered. Little things like that make you look sloppy.” My dad is growing old and can’t remember much these days but I’ll never forget that lesson. Little things matter.
The guys I know with the best style don’t spend thousands a year on clothes. They know how to take care of their clothes and buy quality for the things they wear all the time. My friend Marcus has been wearing pretty much the same outfit for years.
Dark wash jeans, button ups, and navy blazers. But everything fits him perfectly and everything he owns is well cared for. Whenever he buys something it’s something that he knows will last a long time.
Before you go crazy upgrading your style stop and take inventory of what you have. Go through your closet with a critical eye.
Donate things that don’t fit or that you honestly don’t wear anymore.
You’d be surprised at how refreshing it feels only to wear clothes that look good on you. This whole jacket situation with Jake got me thinking about how I approach upgrading my wardrobe. I try to focus on one category at a time when it comes to adding things to my closet.
Right now I’m focusing on getting lightweight jackets for spring. Last fall I wanted to invest in sweaters. Breaking it up by categories doesn’t overwhelm me and helps me improve my style over time.
There’s no need to fix everything at once. The nicest compliment I ever received about my style wasn’t about the clothes I was wearing. It was from one of Emma’s friends I hadn’t seen in years. “You look like the same dude but way better,” she said.
That’s what happens when you take the time to upgrade your style. Instead of trying to become someone else, you simply dress like the best version of you.
