How Not to Dress Like a Frumpy Dad

Photo credit: Cladwell

Let’s face it, dads don’t have the best reputation as being the most fashionable ones in the house. Pleated pants, Crocs, white socks with Birkenstocks. All fashion faux pas that have haunted us dads forever. Fear no more. You too, can be as stylish as your kids rocking the latest and greatest in fashion from your nearest retailer.

Blake Smith and Chris Merchich, the duo behind, a site “empowering men to live confidently” through their clothes, join us with some tips on how to spiff up your wardrobe, keep it simple, and not spend a lot of money. 

Be sure to listen to the guys on this week’s podcast (8/20). Click play on the audio player to the right, or download with the link below.


Blake Smith, Co-founder

What are the most common mistakes guys make when buying clothes?
BLAKE: Keeping stuff that you know looks bad. If you don’t like it, get rid of it. It is better to wear a small amount of clothing that you love, than a huge variety of clothing that you hate.

CHRIS: Not knowing what colors look best on you or what size you are.  Sure, sometimes the sales guy can help, but sometimes that guy is supposed to be working in housewares and is only in the men’s department because he wanted to pick up an extra shift.  With a little knowledge, not about fashion per se, but about yourself, you can trust that you’re at least not going to buy something that doesn’t fit or clashes with your coloring - and if you can do that, you’re more than halfway there.

What basic clothing items should every man own?
BLAKE:  Great question. It depends on a lot of variables - that is actually what we do with The Wardrobe at Cladwell. We look at your build, work environment, social life, budget, and personality, then create a custom list of the basics that you need to look great everyday - in priority order based on what you’ll use most.

CHRIS: It really does depend on the guy, like Blake said.  Build a wardrobe like you build a house, for the every day, not for the exception.  Spend the time and money on the living room (jeans for a lot of guys), not on the formal dining room that only gets used twice a year (suits for most).

What items should a guy be willing to spend more on to get a better quality product?
BLAKE:  Leather things. (e.g. shoes, belts, wallets, watch bands, etc.) They can typically last a long time and make your grandkids look cool.

How does one go about buying sunglasses that will best fit his face?
BLAKE:  There are some pretty standard rules on face shape and what looks best. (see here for example.) Or just fill out a 30 second survey with Cladwell and we’ll pick the best ones for you.

Does it matter what brand of jeans a guy purchases?
BLAKE: Yeah we think so. Some jeans are made by kids in sweatshops, I think we should avoid those brands. Outside of that? It depends on your short term budget. Buying slightly nicer jeans is a better investment over the long-haul, but if you are cash strapped sometimes you need to buy something cheap.


Chris Merchich, Co-founder

When picking out a dress shirt what should someone be looking for?
CHRIS: Focus on the cut of the shirt.  Since dress shirts are tucked in when worn, it’s easy to get that billowing at the sides.

What items should a guy throw away right now if he has them in his closet (crocs, tall white socks…etc)?
BLAKE: Things that you don’t think look good. We have enough challenges already as men, as dads, why go out everyday disliking how you look? In terms of specific items, it really depends on what you want to communicate about yourself. Mark Zuckerberg wears hoodies and sandals, and it tells people that he is young, nerdy, and crazy successful. I think that vibe is serving him pretty well.

CHRIS: Blake said it well, but there really aren’t many things that a guy can’t pull off.  One thing that does come to mind is carpenter jeans.  Most of us haven’t worn these since middle school for a reason.  Even so, it’s nice to have a place to hang your claw hammer.

How does one dress casual but still look stylish?
CHRIS: Having clothes that fit well is the very best way to look like you’ve put some thought into what you’re wearing, no matter how casual.  I’ve finally managed to get rid of the old basketball shorts I’ve had since college that stretch down past my knees.  I’m 5’11″ and shorter shorts make me feel and look taller, even if I’m just wearing them to exercise.

What can a guy do to insert a little personality in to his wardrobe without going overboard?
CHRIS: This is a great question and I want to call out the difference between adding personality to what you wear and adding visual interest.  The truth is that your personality is communicated through your clothing whether you’re thinking about it or not.  And that’s part of what makes clothes so interesting.  If you’re a guy who sees a well styled mannequin at the mall and copies it exactly (like I used to do), well that tells me something about who you are, even if it’s not very visually stimulating.  We in the fashion world should appreciate that.  If you want to make that outfit even more personal and simultaneously make it more visually appealing, there are a lot of ways to do that.  What are your hobbies?  If you love the outdoors, maybe you wear a Patagonia jacket wherever you go, make that your signature piece.  Maybe that unexpected thing is a watch you inherited from your grandfather.  Or maybe you have something from your childhood that you can still wear.  As crazy as it sounds, I can still fit into this old t-shirt I wore for art class in elementary school.  It was down to my knees then.  Now my wife likes to sleep in it.

What basic tips could you share with someone trying to update his style?
1) Look at your lifestyle - what do you wear regularly?
2) Throw away everything else.
3) Only buy something you really really like.

CHRIS: If you’re looking to update, ask someone for help who you can trust and be ready to get pushed a little outside of your comfort zone.  Realize that the probable reason you haven’t changed is because you’ve been comfortable with what you’ve been wearing - and the new thing will probably be different and maybe a little anxiety inducing.  But that’s okay.  Usually after you wear something or twice you don’t even think about it.

What was your inspiration for founding Cladwell?
We started Cladwell because we needed it. We had out own experiences where we realized that what we wear makes a difference, and we knew firsthand how stupid and stressful it can be to find the right clothes. So we figured we weren’t the only ones, and decided to do something about it.

What is Cladwell’s mission?
If you don’t like it, get rid of it. It is better to wear a small amount of clothing that you love, than a huge variety of clothing that you hate.

This interview is part of our ongoing series with leaders from companies involved in parenting products or issues. No goods or services were exchanged. Who would you like to hear from? Leave a suggestion in the comments below.

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