Building a Dad Wardrobe That Works for Your Day Job AND Your Side Hustle

Man, I never thought I’d be taking wardrobe advice from watching my buddy change clothes in a Starbucks bathroom, but here we are. Last month I’m sitting there with my coffee while Jackson’s at soccer practice, and this guy Mike – works at some marketing firm downtown – literally disappears into the restroom looking like he stepped out of a corporate handbook and emerges five minutes later looking like he runs a trendy design studio. Same pants, completely different vibe. Turns out he teaches evening classes at the community college and needed to shed that “corporate suit” energy before walking into a room full of art students.

Got me thinking about my own wardrobe situation, which honestly has become way more complicated than it used to be. Sure, I’ve got my main gig as an IT project manager, but like most dads I know these days, that’s not where it ends. I write about men’s style on the side, occasionally help out at a friend’s clothing store when they’re swamped, and sometimes do workshops for other parents trying to figure out how to dress like adults again. Each thing needs me to look… different. Professional but not stuffy. Knowledgeable but approachable. Put-together but not like I’m trying too hard.

The thing is, as a dad you can’t exactly maintain three separate wardrobes. First off, kids are expensive and there goes half your budget right there. Second, I’ve got maybe ten minutes to get dressed in the morning before Sophie needs help finding her backpack or Jackson realizes he forgot about some school project. I can’t be standing there trying to figure out which version of myself I need to be today and what that means for my outfit choices.

So I’ve had to get smart about building what I call a “shapeshifter wardrobe” – clothes that can handle my regular dad duties but also adapt when I need to switch professional gears. It’s taken some trial and error (and yeah, some fashion mistakes along the way), but I’ve figured out a system that actually works without breaking the bank or requiring a master’s degree in styling.

The foundation of the whole thing is buying pieces that can genuinely work in multiple situations. I’m talking about the wardrobe workhorses that don’t look out of place whether I’m on a video call with my team, helping customers at the store, or leading a workshop for other dads. These aren’t trendy pieces or statement makers – they’re the reliable, versatile basics that form the backbone of everything else.

For me, that starts with really good dark jeans. Not the cheap ones that fade after three washes or the designer ones that cost more than my monthly coffee budget. I’m talking about solid, well-made denim in a straight cut that looks intentional but not overly styled. Dark enough to pass for business casual when needed, quality enough to look like I know what I’m doing when I’m talking about clothes, comfortable enough to chase kids around in.

Then there’s chinos in colors that actually make sense – navy, olive, gray. Not the khaki ones that show every stain (learned that lesson the hard way during Sophie’s spaghetti phase), but darker colors that can handle real life while still looking professional. The fit matters here too – not so slim that I look like I’m trying to be twenty-five again, not so loose that I look like I’ve given up entirely.

Button-down shirts are probably the most versatile things I own. White and light blue oxford cloth, nothing fancy, but good quality that holds up to repeated washing. These things are like clothing chameleons – tucked in with chinos and dress shoes for work calls, untucked over a t-shirt with jeans and sneakers for weekend retail shifts, sleeves rolled up for workshop teaching. One shirt, multiple personalities.

And here’s something I learned the hard way: invest in really good basic t-shirts. Not the three-pack ones from the big box store that shrink and lose their shape after a month. I mean well-made cotton tees that actually keep their structure and don’t look sloppy. These work as undershirts when I need to layer, standalone pieces when I’m going for casual, or foundation pieces that can be dressed up with the right jacket.

Got a couple of merino wool sweaters too – navy and gray crewnecks that work over everything and can handle Texas weather when it actually decides to cool down. Merino’s great because it doesn’t wrinkle like cotton, doesn’t smell after one wear, and somehow manages to look both casual and professional at the same time.

The real game-changer though is having one really good blazer. Nothing too fancy or structured, just a navy jacket that can completely transform whatever I’m wearing underneath. Jeans and a t-shirt with this blazer? Looks intentional, maybe even stylish. Chinos and a button-down? Boom, ready for client meetings. It’s like having a superpower in your closet.

But having good foundation pieces is only half the battle. The magic happens with what I call “quick-change artists” – the items that can completely redirect how people perceive the same basic outfit. And the biggest game-changer here is shoes. I’ve got three pairs that do most of the heavy lifting: clean white sneakers, brown leather loafers, and casual boots. Same jeans and button-down reads completely different depending on which shoes I throw on.

Sneakers make everything look younger, more approachable, like I actually get it when I’m talking to other parents about practical style. Loafers dress things up without going full corporate – perfect for when I need to look professional but not stuffy. Boots work for almost everything and are practically required here in Texas anyway.

Jackets are another quick transformer. I’ve got a lightweight field jacket that makes any outfit look more outdoorsy and practical, perfect for the store work. That blazer I mentioned can elevate anything. And yeah, I’ve got a leather jacket that probably makes me look like I’m having a midlife crisis, but sometimes you need that edge when you’re trying to prove you haven’t completely surrendered to dad life.

The little details matter more than I used to think too. Switching from my everyday Casio watch to something leather-banded makes the same outfit look more intentional. Different bag – canvas tote for casual stuff, leather portfolio when I need to look more serious. Even things like glasses frames can change the whole vibe, though I’m not coordinated enough to switch those out regularly.

What I’ve learned is that each of my different roles has its own visual language, and you’ve got to speak enough of it to fit in without looking like you’re wearing a costume. For my day job, it’s about looking competent and reliable – clothes that fit well, nothing too trendy, clean and maintained. When I’m writing about style or doing workshops, people need to believe I actually know what I’m talking about, so details matter more. The specific shoes, how things fit, little touches that show I pay attention to this stuff.

For retail work, it’s all about being approachable and practical. Can’t look too fancy or customers think you’re judging them. Can’t look sloppy or they don’t trust your opinion. And everything has to be comfortable enough to stand for hours and move around in. Usually means jeans or chinos with some stretch, comfortable shoes, layers I can adjust as the store temperature changes throughout the day.

Teaching workshops to other parents is probably the trickiest balance. Need to look like I have my act together enough to give advice, but not so polished that I seem out of touch with the chaos of family life. Usually go with chinos instead of jeans, button-down over a t-shirt, and shoes that split the difference – like desert boots or really clean sneakers.

The whole system works because I’m not trying to be a different person for each role – just adjusting the volume on different aspects of who I already am. The clothes become tools that help me shift gears mentally too. When I switch from sneakers to loafers, I’m not just changing shoes, I’m transitioning into a more professional headspace.

Practically speaking, the biggest challenge is when I’ve got multiple roles in the same day. Had a situation last week where I had a morning video call, lunch meeting with someone about a potential writing project, then had to pick up Sophie from school and take her to the store with me for an evening shift. That’s three different dress codes in one day, and I can’t exactly go home and change between each one.

So I’ve gotten strategic about layering. Started the day with a good t-shirt, button-down over it, blazer over that. Video call with the blazer on, professional and clean. Lunch meeting, ditched the blazer but kept the button-down – still looked put-together but more approachable. Store shift, lost the button-down, just t-shirt and jeans. Same foundation, three different looks.

Keep a small bag in my car with backup options too – extra shirt, different shoes, maybe a different jacket. Not enough for a complete wardrobe change, but enough to adjust the vibe when needed. And honestly, sometimes I just have to accept that I’m not going to look perfect for every situation. The goal is “appropriate enough” not “perfectly dressed for the specific context.”

The psychological piece of this is real too. The right clothes help me get into the right mindset for whatever I’m doing. When I put on the blazer, I feel more professional, more prepared for business conversations. When I switch to the field jacket and boots, I’m ready for hands-on work. It’s like costume changes that help you access different parts of your personality.

What I’ve learned is that you don’t need a massive wardrobe to pull this off – just the right pieces that work hard for you. I’ve probably got thirty items total that create enough combinations to handle all my different professional needs. The math works out way better than trying to maintain separate wardrobes for each role, especially when you’re already spending half your income on soccer cleats and school supplies.

The key is being realistic about what you actually need versus what magazines tell you you should have. I don’t need five different blazers or twenty pairs of shoes. I need a few really good pieces that work across multiple contexts and can be mixed and matched efficiently. Quality over quantity, versatility over specialization.

And honestly, most people aren’t paying as much attention to your clothes as you think they are. They’re just registering whether you look appropriate for the situation and whether you seem to have your act together. You don’t need to be a fashion expert to pull this off – just someone who thinks strategically about what they’re putting on.

The side hustle life isn’t going anywhere. If anything, more dads I know are picking up additional income streams, whether it’s driving for rideshare companies, freelance work, teaching, or starting small businesses on the side. We’re all juggling multiple professional identities, often within the same day. Your wardrobe can either make that easier or harder.

I choose easier. Which means clothes that adapt to my life instead of me having to adapt to my clothes. Foundation pieces that work across contexts, strategic additions that can shift the whole vibe, and enough flexibility to handle whatever combination of roles my day throws at me.

Because at the end of the day, whether I’m managing IT projects, writing about menswear, helping customers find clothes that fit, or teaching other parents how to look put-together, I’m still the same person. The clothes just help me show different facets of who I already am, depending on what the situation calls for. And if that occasionally means changing shirts in a Starbucks bathroom like my buddy Mike, well… we do what we have to do.