I wish I knew that fit is more important than brand when I was wasting money in my teens.
The Designer Shirt That Looked Worse Than My H&M One
In high school, I saved up for a designer t-shirt with a big, flashy logo. I thought wearing that brand made me cool. But the fit was boxy and unflattering. The same week, I bought a cheap t-shirt from H&M, but it fit me perfectly—snug on the chest and arms. I got more compliments on the $10 H&M shirt than I ever did on the $150 designer one. It was a hard lesson that the silhouette a garment creates on your body is far more important than the logo printed on its fabric.
I wish I knew to invest in timeless basics instead of fast-fashion trends when I was 20.
The Revolving Door of My Old Wardrobe
At 20, my wardrobe was a collection of cheap, trendy items from fast-fashion stores. I’d wear a shirt a few times before it would shrink, fade, or simply go out of style. I was constantly buying new clothes but always felt like I had nothing to wear. I wish I had taken all that money I wasted and invested it in a few timeless, high-quality pieces instead: a great pair of dark jeans, a classic white Oxford shirt, a well-made leather jacket. Those pieces would still be in my closet today.
I wish I knew a tailor could make my cheap clothes look expensive when I was in college.
The $25 Secret Weapon
In college, I bought a cheap suit for an internship interview. Off the rack, it looked exactly like what it was: a cheap suit. It was baggy in the shoulders and the trousers were too long. I almost didn’t wear it. A friend told me to take it to a local tailor. For about $25, she transformed it. She took in the jacket and hemmed the pants. Suddenly, my cheap suit fit like it was custom-made. It was the best style investment I ever made. A tailor is the secret weapon for looking like a million bucks on a budget.
I wish I knew how to build a cohesive wardrobe around neutral colors when I was starting my career.
The Closet Full of Clothes That Didn’t Match
My first “professional” wardrobe was a chaotic explosion of color. I had a green shirt, purple tie, and brown pants, and none of them went together. Getting dressed for work was a daily struggle that gave me anxiety. I wish I had known the simple secret of building a wardrobe around a base of neutral colors: navy, grey, white, and black. When every piece in your closet complements every other piece, you can create an infinite number of sharp, put-together outfits with minimal effort.
I wish I knew that good shoes are the foundation of any great outfit when I was only wearing sneakers.
The Boots That Changed How People Saw Me
For years, my only shoes were running sneakers and a pair of beat-up skate shoes. I wore them everywhere, even with chinos and a button-down shirt. I thought it looked fine. When I started my first real job, I invested in a single pair of classic, brown leather Chelsea boots. The change was immediate. They elevated every single outfit I owned, adding a level of maturity and polish. People at work started treating me with more respect. I learned that you can tell a lot about a man by his shoes.
I wish I knew how to layer clothes properly to add dimension when I was younger.
The Third Piece Rule
My outfits used to be very one-dimensional: just a t-shirt and jeans. It was fine, but it was boring. I couldn’t figure out why some guys just looked cooler and more put-together. Then I learned about the “third piece” rule. By adding a simple third layer—an unbuttoned shirt over the tee, a lightweight jacket, a cardigan—you instantly add depth, texture, and visual interest. It’s the simplest way to take a basic outfit from forgettable to stylish.
I wish I knew that a good watch was a better investment than a dozen graphic tees when I was 18.
The Accessory That Lasted Longer Than My Wardrobe
At 18, my style was defined by a collection of cheap, trendy graphic tees that I thought were the peak of coolness. They all faded, cracked, or were cringe-worthy within a year. For my birthday, I got my first real watch—a simple, classic design. Ten years later, all of those graphic tees are long gone, but I still wear that watch every single day. It has been the single most versatile and timeless style item I’ve ever owned. I wish I had invested in that kind of quality from the start.
I wish I knew to find my own personal style instead of just copying others when I started caring about clothes.
The Costume I Was Trying to Wear
When I first decided to upgrade my style, I found a blogger I admired and tried to copy his exact look. I bought the same clothes, the same shoes, everything. But it never felt right. It felt like I was wearing a costume, like I was playing a character. I learned that style isn’t about imitation; it’s about inspiration. You should take ideas from others, but then filter them through your own personality, lifestyle, and body type to create something that is uniquely and authentically you.
I wish I knew how to match my clothes to my skin tone when I was first building a wardrobe.
The Color That Was Draining the Life From My Face
I once bought a mustard-yellow sweater because it looked great on the store mannequin. When I wore it, however, something was off. My skin looked pale and washed out. A friend who was an artist pointed out that the color was clashing with my cool skin tone. She suggested I try jewel tones like emerald green or sapphire blue instead. The difference was incredible. The right colors made my skin look vibrant and healthy. I realized clothes don’t just have to fit your body; they have to complement your natural coloring.
I wish I knew that having fewer, better-quality items was superior to a closet full of junk.
The Purge That Gave Me More Options
My closet was packed so tightly I could barely close the door. It was full of fast-fashion bargains and clothes I “might wear someday.” Yet, every morning, I had the same feeling: “I have nothing to wear.” I finally did a massive purge, getting rid of everything that wasn’t high-quality and a perfect fit. I was left with a fraction of my clothes, but suddenly, I had more outfits than ever before because everything I owned was something I genuinely loved and could build an outfit around.