Alright, let’s talk about figuring out what to wear for sales. When I first got into this game, I really didn’t know what the heck to do. I saw all these pictures of sharp-dressed folks in suits, looking real serious.
So, what did I do? I went out and got myself a couple of suits. Felt like I was playing dress-up, honestly. Walked into my first few meetings feeling stiff, awkward. Like the clothes were wearing me, you know? It just didn’t feel right, didn’t feel like me.
Trying Different Stuff
After sweating bullets in those suits for a while, I started looking around more. Saw some guys rocking the super casual look. Jeans, t-shirts sometimes. I tried that for a bit, but swung too far the other way. Felt sloppy, like I wasn’t respecting the client or the job. Didn’t feel confident walking in like that either.
Then came the whole ‘business casual’ phase. You know the look:
- Khakis or chinos
- Button-down shirts (usually blue or white)
- Maybe a sweater
- Loafers or some other ‘business appropriate’ shoe
This was better, definitely more comfortable than the suit. But still… it felt kind of bland. Like I was wearing a uniform anyone could pick up off the rack. Didn’t really stand out, didn’t feel very authentic.
What Finally Worked for Me
The real change happened when I stopped thinking about rules and started thinking about the situation and feeling comfortable. Who was I meeting? What was their company culture like? Was it a formal boardroom or a casual coffee shop?
I started building a core wardrobe of stuff that looked good, fit well, and felt comfortable. Stuff like:
- Good quality dark wash jeans (no rips!) or well-fitting chinos.
- Solid color button-down shirts that actually fit my shoulders and arms. Learned to roll up the sleeves properly too.
- A few decent sweaters and maybe a quarter-zip pullover.
- A versatile sport coat or blazer I could throw on if I needed to step it up a notch. Not a suit jacket, something a bit more relaxed.
- Clean, decent shoes. Seriously, people notice your shoes. Doesn’t have to be expensive, just clean and not falling apart.
So, my process now is simple. Before a meeting, I think about who I’m seeing and where we’re meeting. I pick from my core stuff. Maybe it’s jeans and a button-down. Maybe chinos and a sweater with the blazer. The point is, I look put-together and clean, but I also feel like myself. I’m not fidgeting with a tie or feeling constricted.
It took trial and error. Lots of it. Wore stuff that was too formal, stuff that was too casual. Eventually landed on looking sharp but feeling comfortable. Turns out, when you feel good in what you’re wearing, you act more confident, and that’s probably more important than the specific clothes themselves. Just gotta look like you care and put in a little effort. That’s been my experience, anyway.
