Learn How to Dress Well (While Still Staying True to You & Not Breaking the Bank)
Every morning as I stood in front of my closet, feeling utterly helpless. I had clothes a lot of them but nothing felt right. I’d put on three outfits, hate all of them then have to resort to wearing the same black jeans and a off white top for the fifth time that week. Safe. Forgettable. Not really me.
It took a friend one of those girls who always looked like she just walked off the hardwood, that type to pull me aside and say kindly but pointedly: “You dress like you’re trying not to get noticed.” She wasn’t being mean. She was right.
I was saying the wrong thing with how I wore this outfit and that one comment drove me to figuring out what speech if any at all I was attempting to deliver. And the conclusion I have found: Dressing confident is hardly connected to trends, expensive brands and a perfect body. Women→ understanding oneself; men → dressing from that understanding vs. despite it.
This is what I want someone to have told me years ago.
Why Your Self-Posses Is More Intertwined With Your Wearings Than You Think
There’s real psychology behind this. It’s called “enclothed cognition” the hypothesis that our clothing influences how we think and what we feel about ourselves. If you wear something that feels like your true self, it alters how your hold yourself. Your voice becomes a little more confident. Instead of on your hem or tugging at the collar every five minutes.
This was something I saw the first time I wore an outfit I consciously chose rather than habitually plucking an item from my closet. That morning I walked into a meeting and someone said “You seem different today. More confident.” All I had done was wear clothing that I actually liked.
It sounds simple. It took real work to make it there though.
Step 1: Determine what you really enjoy (not what you feel like you ought to like)
This part is where people most often get it wrong, and that includes myself.
We are inundated with fashion Instagram, Pinterest, TikTok outfit videos to the point that many of us end up dressing for an imaginary audience rather than innovating and inventing our own wardrobes. I had a Pinterest board based on all the minimalist beige aesthetics that looked amazing on other people and made me look like I was in line for a dental appointment.
What actually worked: I started a note on my phone titled: What I Actually Wore and Felt Good In. Not what sounded good on paper not what I put on and then forgot about because it didn’t feel awkward, or elicit self-doubt, all day long.
Two weeks in, the trend begun to solidify. I felt best in:
Sharp edgey (clean blazers, not floppy cards) structured pieces
Bright colors not pastels, not neutrals.
Textures ribbed knits, linen, anything with a little weight
That was all outside my Pinterest board. None of this was in vogue at the time. But it was me.
✦ Do this: Over the next two weeks, pay attention to how you dress on your best days when you feel peak-is; sharp; capable; confident. Look for the patterns. HINT: They are already contained in your wardrobe.
Step 2: Learn Your Body, NOT How Fashion Magazines teach you.
For years, I learned to “dress for my body type” following what was spoken about in magazines: hiding this, minimizing that, achieving the “illusion” of something else. It was draining, and if I am honest, a little insulting to me.
But I made a change in my brain from how do I dress to look like this shape to what proportions are comfortable for me?
I learnt that I like high-waisted trousers because I like how they make me feel (structured, intentional, not at risk of losing my pants if I moved faster than a snail’s pace), NOT because they theoretically make me look taller (something I’d read). That practical reason so happened to be attractive. Comfort and ease not manipulating perceptions was the point of departure.
What actually works:
Experiment with clothes without criticism The first bodily sensation I notice at the time of noticing.
If you are constantly yanking something down, pulling it up, or fiddling with it — it’s not working for your body as a garment except the size.
Fit matters more than size. After all, a perfectly fitted medium always trumps a sloppy small or stretched large.
Having some wardrobe essentials altered by a local tailor was one of the best investments I made. The fact is, a ₨1,500–₨2,000 (or $10–$15) hem on trousers or taking in the waist of a blazer can entirely change how an item looks and feels.
Step 3: Create A Colour Story That You Truly Own
And here’s where I did this for years: Around “neutral basics” because every style guide told me too. And then every morning I felt bored and uninspired.
Now here is the secret of neutral basics, they will only go well with someone who likes neutrals very much in their clothes. If your joy of life is beige and cream and white wonderful, start with this. However, if you’re vibrant in shades like forest green and rust and cobalt blue (that is not typically popular), a greige wardrobe won’t give you confidence. He will make you feel as if you’re dressed as someone else and walking in his shoes.
How to discover your color story:
Take everything out of your closet and sort it by color. What do you already go to most often? That’s a clue.
What colors do you get complimented on versus what colors do people ask if you are sick today? when you wear them.
See some photos of you in which you really feel good. What are you wearing?
For this, you certainly don’t need a professional color follower (Colorwise is great for that—and testing the waters with even just a Seasonal Color quiz online can serve as fun starting points). You just have to listen to what the feedback loop of your life is already telling you.
Things got dramatically easier as soon as I decided to build around my real colors dark greens, warm browns and the occasional pop of mustard yellow. Things matched more naturally. My spending decreased because I lost my compulsion to buy things that did not match with anything else I owned.
Step 4: Get Yourself a Signature Something That Is You!
This is the phase people often skip, and one I think of as where get-dressed stops being an exercise in not-bad-ness and starts to be truly expressive.
It doesn’t need to be dramatic; a signature sniper. It can be something small:
You always wear cool earrings.
You always have a watch
You constantly sport some sort of collar
You’re constantly rolling your sleeves up
You wear boots at all times of the year
This was a mam for me → structured shoulders + at least one pop of color. Blazers with a surprising lining. The bright bag with an otherwise peaceful ensemble. Small, consistent, mine.
That got associated with me by others. “That jacket is so you.” Which was powerfully amazing not because I wanted to be goddamn trendy, but because I felt seen the way I wanted to be seen.
Consider the people whose personal style you aspire to embody. More than likely they have a signature also something you would recognize even if you had no idea who wore the outfit. It doesn’t have to be wild. It just needs to be consistent and deliberate.
Step 5: Stop Buying Clothes and Start Creating a Wardrobe
These are not the same thing. I used to buy clothes 24/7 and still had nothing to wear. The whole everything changed when I grasped the difference.
Buying clothes is a reaction a discount, or a fad, something that hung nice on the rack. Creating a wardrobe is purposeful filling gaps, choosing pieces that function with what you already have on hand, considering cost-per-wear instead blindly buying based on price tags.
The gaps-first approach:
Take 20 minutes to spend with your real wardrobe before you head out for whatever craziness may be on sale today. Ask:
One: What do I always reach for that I have only one? (For me, dark pants I had a pair I lived in)
What events do I regularly dress for when I always feel overdressed or underdressed?
What’s out there dangling with no pairing?
Shop to fill those gaps. Not to browse. Not to see what’s new. To solve specific problems.
Something like Stylebook (iOS) or even just a shared Google Photos album, where you photograph your wardrobe and can see what you actually own which is astonishingly not the same as what you think you have. Doing this exercise I found three items hanging in my closet; long forgotten.
Step 6: Dress for life you are actually living (not an Instagram filtered version of it)
This is one of the most useful things nobody tells you.
I bought things for a life that never existed. Gorgeous silk shirts I had no place to wear. Forty-minute heels, the ones that my feet would have revolted by forty minutes in. The leather jacket that looked awesome on the rack and made me sweat buckets whenever I put it on.
Dressing with confidence is dressing for your actual life. If you work from home three times a week, your closet needs to prove it. The bus is fine right now, but if you commute by public transport your shoe game has to be practical-first. If you have a vibrant social life at all, that is an investment worth pursuing.
Map your actual week. How many days a week do you need: It needs to be how many times per week
Workwear?
Casual weekend clothes?
Smart-casual (the only category most people will struggle with)?
Exercise or activewear?
Evening/going-out clothes?
Then look over your clothes and see whether the ratio of what you own to need is roughly equal. Most people I know have the opposite a slew of what we all call “going-out” clothing (ten nice things to wear when they leave the house) and two pairs of truly good casual pants that get recycled in and out.
Things That Kill Your Confidence
Strutting in stuff that does not fit because they were expensive.Price and fit are disconnected. Ill-fitting luxury is way more nasty than ill-fitting affordable.
October 2023 You buy for who you want to become not who you currently are. The pile of clothes “I can actually wear this when I lose X kilos” is the biggest confidence booster killer. Dress your actual body today.
Jumping on trends that are not for you. Not all trends, are for every body. What doesn’t feel like you, isn’t no matter how trendy.
Underestimating the power of grooming. CARE: Not even the finest of outfits will make an impact if the hair, skin or shoes are unattended. Confidence is a complete image derived from clothes.
Putting on things that aren’t comfy and praying for you to get used to it; You won’t. Shoes that hurt in the shop will kill you over six hours. A waistband that digs in when you sit will annoy you all day long. There is no genuine confidence without comfort.
Ignoring the occasion. Dressing “confidently” is not about dressing the same in all places. Dressing to the occasion, which is part and parcel of being socially confident, then making that appropriate outfit your through detail.
Let´s Be Real: It Takes Time to Build Confidence.
So, to be real, I am skipping over this part a lot because no one writes about it.
I was terrified when I wore the first outfit that really expressed this (bold color, interesting silhouette, nothing “safe” about it). I hesitated three times before stepping out of the house. I nearly changed into a neutral outfit.
I didn’t. It was one of the best days I had in a long fucking time.
But that fear didn’t go away straight away. It was not until weeks of practicing deliberate dressing that it became second nature. All before I stopped dressing for the imaginary critics and starting dressing for myself.
If you’re in the earliest stages of this process, that’s fine. Start small. If a full look seems even just a bit excessive, go slow and introduce one expressive piece at a time. Wear the earrings. Buy the color. Try the silhouette. See what happens.
The commonest response is, : nothing terribly bad. Others care much more about their own looks than they care about your looks. And the ones who do notice? Usually, they say something nice.
Overwhelmed, What to Start With
If you are confused and feeling nauseous right now here is a simple entry point.
This Week: Wear One Thing YouHave Been AvoidingBecause It Felt Like Too Much, Not Safe See how you feel.
UPDATE : This month\’s mission The closet audit Pull everything out. Only keep what truly fits and feels good Donate the rest.
Next purchase: Shop with intention. One specific gap to fill. Not browsing.
Longer term: Identify your signature. Something you have which is so small, and indivisible ty yours always.
STYLE CONFIDENCE IS NOT ABOUT CLOTHES It is about having your clothes, that you have chose for yourself, that you wear unapologetically and then edit up as you grow.
Your wardrobe should speak with the world like it is a conversation between you and the world. Verify that it is saying what you want it to say.
The most stylish people I ever met were not the ones who always wore the freshest clothes or followed fashion trends. These were the folks who knew exactly how to present themselves and taking note of that. That’s available to everyone. Including you.