When does it make sense to spend more on your looks?!

Didn’t think I’d be blogging about *looks* today, but I’d be lying if I said this stuff hasn’t crossed my mind in the past either :) Maybe you’re the same?

Here’s a convo I recently had with a reader, and would love to get your take on it too…

Is it all a bunch of malarkey, or are there certain times when spending more on our looks just makes more sense?!


Let me tell you something which opened my brain on purchases this last year. This is a memorable purchase for me which really surprised me.

One of the things that I have been rethinking is how much I get out of what I purchase. For an example, your Goodwill story. I love Goodwill and shop there all the time. I know you can get great deals there.

Last year I met up with a life insurance agent who cleared $300k last year and he was telling me how he bought these suits at $1k-$3k price points. I was shocked and told myself I would never. Clothes depreciate. What a waste.

Then it struck me. He made almost 3x money as me last year! Maybe he understands something I do not. I still shop at Goodwill, but I started buying very nice and expensive Polo shirts after this thought struck me. Direct from Polo at $80 a piece. I thought if I presented myself better and opened stronger with a new nice Polo shirt it might help me generate more business like my friend.

I’m a realtor and as soon as I did this I started getting much more respect and picking up clients at a faster rate. I just inked a contract for a $340k property from one of my last open house leads. That’s a $10k commission check from an $80 shirt purchase.

Of course, some may say that it’s just in my head and maybe I got lucky, but the reality is that I did feel more confident in my abilities to close more business for myself. I feel that’s 100% worth it.

If I was on the outside watching myself buy a piece of clothing for $80 I would shake my head and think how superficial. But now I have been buying branded t-shirts that say “Realtor”, “Real Estate Agent”, “I sell real estate,” etc and still to this day when I order off eBay I cringe. I never have paid $20-$40 per shirt as most of my clothes have always been hand me downs from growing up in a family of 6! And I’m the Goodwill guy like you.

That being said, the opportunity for my business and ROI from being a walking billboard and spending just a little bit more to “redeem” a depreciating asset is amazing to me. This took me by surprise, and made me think to myself that maybe cheap is not always best in every circumstance. I feel strongly that if I had worn my Goodwill polo shirt at that last open house it would have been more difficult for me to close that deal.

I always used to wonder why the Uber rich purchase things that don’t make the most sense to the rest of us, but maybe your money really is a mirror of your priorities. By prioritizing my appearance and professional image and nothing more, I was able to pick up more clients for my business.

What are your thoughts around this?


Here’s what I wrote back, which may surprise you?


I think you could be very right on that!

And even if it IS just in your head, does it really matter since business is booming?! :) I’d be buying $80 shirts left and right too if I was experiencing that, haha…

So I say keep going with it and see how far you can take it. What does your car look like for example? Whenever I see realtors in Beemers and Benzes I’m always thinking they’re much more successful/skillful whether it’s the truth or not.

In areas where perceptions matter like in realty/sales/etc I def. think it’s worth “putting on a show” more, so long as it doesn’t go overboard. You only need so much to milk 90% of the rewards, and you could pick up a 7 or 8 year old luxury car for the same as you can a normal car but get that “oomph” out of it.

So yeah man – I’m with you! Sometimes spending money really DOES help you make money in the end. Just gotta know *where* to spend it :)

Let’s see if you can get close to that $300k this year!


We went back and forth a little bit more (turns out he already rocks a luxury car), but that was the gist of it all. Spending more in order to gain more – in this case with business. It sounds stupid and really shouldn’t matter at all what you wear/drive/etc, but perception is a silly thing and sometimes you have to play the game.

My thoughts on it anyways. Ever catch yourself spending more in certain areas to get better results?! Whether in career or goals or *cough* love? What do you wear on a first date – your everyday duds or your nicer ones? ;)

I remember being a realtor myself years ago and how lame I looked rolling around in my bright yellow Ford Mustang when I was trying to get people to take me seriously. I had no problem with those who already knew me (my only sales! Hah!), but I guarantee I would have been more successful had I *looked* the part more. Thank God I had normal hair at least!

On the flip side, it eventually led me to becoming a professional blogger which ironically means wearing unprofessional clothes too, haha, so this stuff can work in the opposite way as well :) The trick is knowing what makes you more credible in people’s eyes and then taking advantage of it.

Agree? Disagree?

ADDENDUM: I was reminded of another article of clothing to consider when trying to boost your confidence/sales ;) From my friend Hélène Massicotte: The Sexy Underwear Trick

[Photo credit up top: distel.com]

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  1. Kate January 14, 2020 at 6:07 AM

    Why not?! If you can afford it and you feel good (and in this case feel professional) then go for it! I spend not a tiny amount on getting a fancy manicure every 2 and a half weeks and always feel great about how my hands look. Who knows if it has helped my career… And my husband didn’t mention my nails on our first date! But one thing I know for sure is that when I was dating and in business meetings I never feel self conscious about my hands. And there was a time when I often did feel self conscious with shitty chipped nails when I saved some coins by doing my own manicures that looked rubbish!

    1. J. Money January 14, 2020 at 1:13 PM

      Haha…. you rock those nails with your bad self.

    2. Christine Luken January 14, 2020 at 1:44 PM

      I agree 100% on the manicures! I think they enhance my professional image, and it’s a form of self-expression. My nails are currently sky blue! I can pull that off and still be professional. Not all of us can rock the ‘hawk like J Money! ;)

  2. Machee January 14, 2020 at 7:22 AM

    I always remembered a saying my favorite manager said. “You get the job you dress for.” She always was in a business suit of some type, which I thought was a little much for a Customer Service Manager at a local bank, but she commanded respect and knew she was in charge, which I think partially came from looking professional. Now that I’m a SAHM mom, I can 100% tell you that clothes can make a huge impact in attitude (jammies all day vs getting dressed, anyone??). I think his ROI was a good one, and buying a handful of nice polos for work isn’t going to break the bank.

    Also, on my first date with my husband, I was in a tshirt, ball shorts, and muddy Chacos, while he was in new jeans and a nice t shirt. I warned him I didn’t look great when we met up for ice cream (I’d been doing yardwork all day), haha. Later, he told me he thought I was testing if he liked me for my looks or if I was just being lazy since we went to the same church and he saw me dressed nice on Sundays.

    1. J. Money January 14, 2020 at 1:14 PM

      Hilarious!! I’d probably wonder if it was a test too :)

  3. Barb January 14, 2020 at 7:23 AM

    I agree as long as you don’t go nuts. Granted, nobody on here is going to go nuts buying something super extravagant for anything! My Goodwill rule is to never buy something that I could buy at Target or Walmart (brand-wise). That ALWAYS guarantees me better quality and appearance. So when I buy my new Ann Klein suit or Black and White blouse, I can simply thank people for the compliment instead of explaining the source! My takeaway from this story is going to be alterations. I buy at Goodwill and do a tuck here, a seam there and honestly I am not the best seamstress. I will splurge on a tailor for my next necessity and feel justified in knowing that it is done right.

    1. J. Money January 14, 2020 at 1:20 PM

      Tailors!! Forgot about them! Are they going the way of the cobblers, or am I just not the target demographic for them?

  4. Leah January 14, 2020 at 7:32 AM

    I think the key element is when he says this:

    “Of course, some may say that it’s just in my head and maybe I got lucky, but the reality is that I did feel more confident in my abilities to close more business for myself. I feel that’s 100% worth it.”

    How the new clothes made him feel is almost (if not more) important than how they look to other people. The confidence element is key.

    In college, I knew a guy who dressed up in a suit whenever he had an exam. I just rocked sweatpants every day (comfort!), but that lesson stuck with me and I use it in my own professional career now and dress for confidence whenever I have a big presentation or meeting.

    1. J. Money January 14, 2020 at 1:18 PM

      That’s true about how it makes you feel.. And some days you can feel *differently* wearing the same piece of clothes too! Exactly why I’ll bring a million different outfits when I travel so I can go with the one that makes me feel best *that day*. Even if my wife makes fun of me for being more of a girl than her ;) (Though in my defense, I can literally fit my entire wardrobe in one suitcase too due to minimalism! Woot!)

  5. vicki January 14, 2020 at 7:54 AM

    Men don’t have as many options for expressing themselves through clothing so if they want to be taken seriously, maybe they do need a branded shirt. I love to look great and shop excessively but not expensively. I like to keep updated but shop Macy’s and get most everything on sale. I am retired so I have the time to check-in at their website frequently to catch the sales.
    Looking pulled together and well dressed doesn’t have to be that pricey. For a man or woman, the clothes are all about what body type you are dressing. After you figure that out just get the best you can afford. Clothing, especially sweaters and knits get pulled and pilled so it would be better to have several from a sale that looks new than one old ratty one.
    Looking good has so much to do with how you carry yourself too. If you hold yourself well, look confident and smile then you are 75% there!

    1. J. Money January 14, 2020 at 1:19 PM

      It is true – us men need more options :)

  6. Debt Free in RVA January 14, 2020 at 8:11 AM

    I think in the case of the realtor and any other sales profession this makes PERFECT sense!!

    Also, my wife shops at Goodwill for me and the kids for a lot of our clothes. However, I do spend extra $$$ on business suits and dress for work. When I go to interviews and compete for jobs I have to wear a nice suit and tie.

    So, bottom line I think for a lot of professions for men and women it makes sense to spend extra and buy nice looking clothes! Great point to consider :-) My suits are about 5 years old now so I think I will buy another one….

  7. Sonja January 14, 2020 at 9:01 AM

    Having been a partner at a law firm looking the part definitely helps. When taking out potential clients, I could see the disappointment when I would drive my Rav4 vs riding in my colleague’s MBZ. Also while in court, if you’ve got a client paying you billable hour rates and you show up in a crappy suit, they will be wondering what you’re doing with the money they are paying you. They definitely want you to look the part. I’ve become good friends with many of my clients and we’ve had the conversation. To a person they indicate that if a person doesn’t pay attention to their presentation it’s as if they don’t care. And if they don’t care about how people view them, then they cannot be persuasive to people they are trying to convince to see things their way. I do not think you need to go overboard, but a few nice pieces can make a difference if your profession demands it.

    1. J. Money January 14, 2020 at 1:21 PM

      All makes sense to me!

  8. Francis January 14, 2020 at 9:07 AM

    Having a few nice pieces of clothes for events (weddings, funerals, business meetings) can pay huge dividends at the right times. One gets to choose how to project your image and direct perceptions of what others have you.
    Appearance matters in business situations and there are certain standards. Fall below the standards and your selling yourself short and missing out on additional margins or opportunities.

    J, when you had meetings to sell your blog, what did you wear during each of the meetings?

    1. J. Money January 14, 2020 at 1:22 PM

      They were all done on the phone or email!

      I didn’t officially meet everyone until everything was signed, and I made sure to wear my best jeans and flannel for it ;) I.e. nothing with holes.

  9. Nora January 14, 2020 at 9:17 AM

    I agree with the post, but at the same time, I’m more likely to trust the quotes from the plumber/contractor who comes to my house and isn’t dressed to the nines. Neat, not fancy, in appearance.

    1. Kristen January 14, 2020 at 9:50 AM

      Good to hear! My husband is a handyman, and his goal is to look like a tidy handyman. He paid extra to get branded t-shirts/sweatshirts, and I’m always amazed by how many leads he generates just walking around town in his gear.

    2. J. Money January 14, 2020 at 1:24 PM

      Totally – you have to *match* the profession you’re in. Dress like a tattoo artist as a doctor and you’re done, just like if you wore scrubs as a lawyer. Gotta know your clients and what makes them the most comfortable.

  10. Tina January 14, 2020 at 9:48 AM

    I would say it’s the confidence that made the difference, not the shirt itself. It’s scientifically proven than when we feel good about ourselves, we exude more confidence/positive energy/etc. On the flop side, if money saving or environmentally friendly practices such as shopping used is a priority, I would suggest being a little more picky about what is purchased. For example, I have my day-today wear and my “first date” (ok – any date as a married with kids woman!) clothes, and then even my work clothes for when senior management people are in town. Most of those all came from some kind of thrift store. Yes, I may pay $7 for a nice shirt as opposed to $3 for an everyday shirt, but it still makes me stand a little taller when I wear it. That said, I also understand the selection at thrift stores for men is much more limited than what women can find (a great annoyance of my husband’s!) so perhaps start that picky looking now while those polos are still crisp to have a shot at finding a similarly nice shirt on the $10 rack before it’s needed! :)

    1. J. Money January 14, 2020 at 1:26 PM

      Agreed, haha… I will get lucky at times and find name brand stuff WITH TAGS ON, but it’s definitely the exception than the rule… The worst is finding something you love, only to catch pit stains on it when you go to try ’em on, bleh…

  11. Christine January 14, 2020 at 10:39 AM

    I think appearances matter, even if we like to think they shouldn’t. And I think confidence matters and if you feel good and put together, you exude confidence. I also think spending more can make a big difference in some things, practically speaking. I spent more on haircuts but they lasted longer and grew out well, so I didn’t have to go as often. And higher quality shoes and clothes also tend to last longer. It makes sense for basic pieces…not for trendy stuff….I guess unless your image requires that! I’m grateful mine doesn’t!

    1. J. Money January 14, 2020 at 1:26 PM

      Same, haha…

      I could be in my underwear for all you guys know right now :)

  12. Savvy History January 14, 2020 at 10:57 AM

    I really enjoy the potential controversy in this discussion. It’s an issue I have thought about myself many times. I know the subject is complex for men, but I personally think it is doubly complex for women because of all the beauty products and the cult of fashion that is continually sold to us and therefore societally expected of us.

    As a young rock musician struggling with my identity and the incessant boy mojo I was around, I took the scruffy route for awhile. I wore a knitted stoner hat, holes in my jeans, and no make-up. With my new history music, I try to dress like a 50s housewife sometimes to match my vintage lyrics with a vintage well-polished appearance. Guess who makes more in tips and money?

    I’m the same person with the same talent no matter how I dress. My mind is blown by the way I’m treated when I look nice or promote my image more. I’m not sure whether to “lean in” and participate more with this or not. As for now, I just experiment and I watch how other women I respect handle themselves. My main take away is that alter-egos are powerful, and sometimes it takes a product or two to fake your way to the alter-ego.

    1. Jane January 14, 2020 at 11:15 AM

      I love that you are thinking about this so consciously. A very scientific approach. I do A, then B. I do X, then Y. So much of our lives nowadays is on autopilot.

    2. J. Money January 14, 2020 at 1:32 PM

      SO COOL!!!!!

      Do you write about these experiments anywhere?!

      Love that you’re trying this stuff out so much… My vote is to keep pushing it and seeing what happens :) The best is when you combine two wildly opposite things like a mohawk and a 3-piece suit or something, haha… That tends to be the Power Look for me ;) nice and professional, but with an edge! And now that I think about it, I only do it when I hit up galas and fundraisers around local preservation and history! It lets me be myself, but not look like a total buffoon around all that Old Money…

  13. Jane January 14, 2020 at 11:06 AM

    You know, somehow that headline did not make me think of shirts.  
    It is ironic (or disgusting) how in this very ageist society, older people who change their appearance to look younger are criticized and reviled. This means that people whose jobs depend on their appearance, like actors, singers, etc., have to hide the fact that they have had plastic surgery (usually multiple times).  My income doesn’t depend on my appearance so I have not had plastic surgery.  On the one hand, I don’t see why people should not have plastic surgery if that is what they want to do.  Their values, their money, no business of mine.  On the other hand, it’s a bit creepy that some people need to have surgery to keep working.  (I’m not a fan of avoidable medical procedures, but, again, it’s their life, not mine.)
    And, in the case of surgery, the calculation is different.  It’s not $80 = a $340 thousand dollar sale.  It’s more like $thousands = maybe get another part or concert.

    1. J. Money January 14, 2020 at 1:34 PM

      Oh man, that’s a whole other world for sure – you’re right. And definitely more skewed towards women than men too :( When we get gray hair we’re considered refined and wiser!

  14. Christine Luken January 14, 2020 at 11:06 AM

    I agree with this 100%! A concept that I taught in my book Manage Money Like a BOSS is YOU 2.0. Essentially you ask yourself what would the next level version of me do? How would I dress? what would I say yes to? what would I say no to? How would I conduct my business? The answer is almost never being cheap with myself if I’m at the next level of success. I actually tell people to create an alter ego to check in with. So when I’m faced with a decision relative to my business, or my life even, I ask what would Queen Christine do? I still enjoy buying my Calvin Klein dress clothes on sale at TJ Maxx. No one knows that I bought them on sale and they still make me feel like 1 million bucks. One thing I definitely splurge on is getting my nails done. Most of my coaching clients are high income, and I noticed that the majority of the women had nice nails. So that something I choose to invest in to raise my professional image.

    1. J. Money January 14, 2020 at 1:37 PM

      That is great!!! Queen Christine! Haha… I do sometimes ask myself “what would J. Money do” when trying to make financial decisions, but I like the idea of pushing it even further ;) Jotting that one down in the “ideas” list – thank you, Queen!!

  15. BC | FrugalWheels January 14, 2020 at 11:21 AM

    This one kind of struck a chord, since I made a similar change recently. I decided after turning 40 I should really start looking more like an adult. Mostly that means I tuck in my shirts now instead of wearing them untucked, and I’ve been going for nicer button downs. Still, some of these come from Goodwill. I did recently buy a London Fog winter coat so I will look a little more professional.

    But to me it’s a balance. When I was buying a house, I didn’t give a shit what my realtor looked like. I cared about the house I wanted to buy. And I would send an insurance salesperson packing no matter what they looked like.

    There’s an old Ferengi saying that applies here: “Never trust a man wearing a better suit than your own.”

    1. J. Money January 14, 2020 at 1:39 PM


  16. Claire January 14, 2020 at 11:33 AM

    I lost my husband a few years ago and I didn’t want people to feel sorry for me. I wanted them to find something else to talk about me apart from my loss, so I bought new stylish clothes. Yes, people would talk about my loss but they could not help talking about how good I looked. I had not known until then that I (apparently) had a beautiful structure, and people started looking at me in a different way – not disrespectfully, but appreciating what they saw. My girlfriends and female colleagues kept on saying how beautifully the bodycon clothes fitted me. I also bought very stylish non-bodycon dresses. At first I was self-conscious but now I am used after five years of both old and new colleagues mentioning the same thing. Fortunately, I had the disposable income to change my wardrobe and this was really good for my mental health.

    1. J. Money January 14, 2020 at 1:40 PM

      Wowwww how fascinating!!

      Would have NEVER thought about doing something like that, that is so cool..

      Loved hearing this, thank you :)

  17. Frugal to FI January 14, 2020 at 12:05 PM

    I have to say it does make a difference, but I harbor this until I went into management. I learned I could not longer wing it on frugal style and expert knowledge. My frugal style had to be upgrade and not by much. A few quality pieces and I gained respect by my subordinates and those above me.

  18. Paula Haataja January 14, 2020 at 1:56 PM

    Great story – and I have a similar one.

    My husband did computer trouble shooting in the telecom industry. After I married him, I suggested that we send his shirts to a shirt laundry – way back in the day when the cost was only 99 cents. He reluctantly agreed. His dress allowed him to stand out in his button down shirt compared to others who came in polos and tees. Within a year he was promoted to management and continued to move upward in responsibility and pay. Clothes do make a difference!

    I still have an ironing board and iron and use it frequently to look my best. We buy quality clothes, but when they are out of season and on sale.

    1. J. Money January 14, 2020 at 2:04 PM

      He married well :)

  19. Kris January 14, 2020 at 6:30 PM

    I agree, as long as you have the funds to spend on the expensive clothes and if it makes you more confident especially in your professional life to earn the big bucks then go ahead and buy the Gucci suits and Tom Ford shoes. Just don’t go too crazy and make it a financial burden on yourself.

  20. Sharon Hansen January 14, 2020 at 9:35 PM

    I enjoy shopping consignment & thrift stores for bespoke and designer brands that I would not be able to afford full price retail. I look for classic items that can span seasons and also unique items (think scarves and necklaces) so that I don’t look like every one else. I am frugal and this principal works for me. I wear a white coat over my clothes, as I work in healthcare, so I just NEED to look neat and presentable, but I WANT to look classically stylish. I replenish my wardrobe quite frequently and donate my gently used items back to independent thrift stores that help people get back on their feet. I do shop at higher end stores and may occasionally buy something but it helps me to keep up with fashion trends. How the clothes help you feel is important. I grew up wearing ill-fitting hand-me-downs. I was never opposed to the second hand nature of the clothes, but if they don’t fit well, the person doesn’t look as presentable and the person knows it (usually). Definitely dress the part you want to portray. An attorney friend recently told me about an intern he did not hire in part because she didn’t dress for the job- despite being told the dress code.

  21. Jill January 15, 2020 at 12:17 AM

    Thankfully I need none of that for my current and hopefully finally profession. I always feel very silly in heels and make-up. The maximum contribution was increased this year for 401ks/457s so I’ll put my hair cut money there!

    1. J. Money January 15, 2020 at 6:20 AM


  22. Chari January 15, 2020 at 9:26 AM

    I have to look healthy, it’s my profession. I have to walk my talk.

  23. John Robertson January 17, 2020 at 3:34 PM

    A book I read in medical school changed my life. It is titled Dress for Success. It is no longer in print. I come from a working-class family and had no idea how to dress upper middle class like a physician. I refused to Wear Ties when they were de rigueur in medical school. This book outlines the scientific reasons why you should dress well.

  24. Rob Weinz January 29, 2020 at 2:03 PM

    My Mother always said to make sure your shoes are shined. Also as a real estate agent I think it is important to look the part. If the company is not giving you their own logo polo shirts to wear than I believe you should be wearing a suit.

  25. Patti February 6, 2020 at 1:43 PM

    My rule is to never drive a better vehicle TO WORK than your boss. Stealth wealth is key when you work for a large company.

    Raises are subjective so it’s always better to be conservative. This is especially important when you work for a very small company as the owner may feel you make enough money and will give you a small raise since you drive a fancier car/truck than them.