Subscribe
Share
Share
Embed
What should you NOT wear in roofing sales? Hats or no hats? Company branded apparel or button downs? Shorts, jeans, or khakis? Best shoes for roofing sales?
Program questions? Call/text: 303-222-7133
“Because your company is only as STRONG as you are.”
Forward-thinking roofers tune in to get help building STRONG companies, sales teams, leaders, systems, marketing, relationships, culture, and financials.
Whether you own a own a roofing company, manage one, or sell roofs - subscribe to the channel for content that will help you:
1) Close even more roofing sales.
2) Adapt to new roofing industry trends and changes.
3) Take control of your roofing marketing and lead generation.
4) Improve D2D roofing sales.
5) Build the roofing company of tomorrow.
Hosted by Adam Bensman
- Started in D2D roofing sales in 2011
- Former Roofing Company COO (multi-state)
- Creator of the Roof Strategist Sales System (used nationwide for retail + storm)
- Founder of The Roofing STRONG Alliance by TAMKO™ (formerly known as the Roofing & Solar Reform Alliance)
- Author of the #1 Best-Selling Book: The Roofing Sales Survival Guide: Beat the Odds, Overcome Yourself, and Win Big
Content produced on or before 5/13/26 was previously produced by The Roof Strategist, TAMKO makes no representations or warranties regarding the content.
What do you wear in roofing sales?
Well, so we're gonna talk about, in
this video, answer the age old question.
What should you wear?
What shouldn't you wear?
How do you present yourself appropriately?
How do you present yourself in a
way that actually feels like you?
And how do you do so in a way that
communicates the right message to
homeowners that you're professional
and they can take you seriously
without feeling inauthentic?
Well, I get this question a lot, so
in this video I just wanna rip the
bandaid off and dive right into what
not to wear first, and then let's go
through from top to bottom, from hats
to what you wear up top to your pants
or maybe shorts and your footwear.
Now, if you agree or disagree, I'd like
to hear from you in the comments because.
Even on stage, I was at
a roofing conference.
I was on a panel, somebody
talked about what to wear.
There was discrepancies
among the folks on the panel.
I invite a v different viewpoints and just
remember, you have to match your market.
I ran training in la.
I've run trainings in Portland and Seattle
metro areas, which are very different
than Columbus, Ohio, which is very
different than Springfield in Minneapolis.
So wherever you are, you just gotta kind
of dress to what your environment is like.
I'll give you an example in Colorado.
I could absolutely get away wearing
this when I'm selling, as long
as I was put together and shirt
tucked in and looking sharp.
But I might look like a weirdo
wearing flannel in another market.
All right, so you just need
to ma match your market.
Now we're gonna get into that
in a minute, but first I wanna
talk about, uh, what not to wear.
And I realize I didn't welcome you yet.
So let's start there.
Welcome or welcome back, uh, Adam
Benjamin here, the roof strategist and I.
Jazzed up to be shooting videos
today and to be joining you.
And thanks for spending your time with me.
So everything I do here, if you're not
familiar yet, is designed to help you and
your team smash your income goal and give
every customer an amazing experience.
And if you haven't done it, I
invite you to join me inside
our new free training center.
It's available@throughstraters.com.
Enter yourname email.
You'll get a login link.
Uh, you can click the
link of the description.
If you're on the fly, just text the word
free, f r e e to the phone number listed.
Which is 3 0 3 2 2 2 71 33.
Alright, let's first talk about what not
to wear because part of giving homeowners
an amazing experience is connecting.
And remember, it's partly how you
wish to be carrying yourself to
how they're gonna be receiving you.
And as we, right before I get into
like what not to wear, Which there's
three main things and then we're
gonna talk about what to wear.
I'm someone who is, I would
like self categorize my style
as like upscale work wear.
You're never gonna see
me overly dressed up.
I like button up, I like jeans and
slacks and I like casual shoes and
it kinda wear works for everything.
I've had some people come up to me
at trainings when I'm wearing a roof.
Branded, uh, sweatshirt saying,
you're not dressing up more for this.
I'm like, what do I need to
be in a three piece suit?
Like it's just me.
And then other people say, Hey,
I really appreciate that you're
dressed in just a sweatshirt.
It shows that you're confident.
It makes you really approachable.
So the reason I'm sharing that
is you can't please everyone.
I'll show up to one event, which
this actually just happened this
last week, and I had someone
say, that's what you're wearing.
And it was a roof strategist, uh, crew
neck sweatshirt that was co-branded
with, with Owen's Corning's logo.
And they were like, that's it.
And then the next time I'm there,
he is like, man, I love that
you're just here and confident in a
sweatshirt and you're so approachable.
So again, you can't please everybody.
You're too dressed up.
You're too casual.
There's just no way around it.
So at the end of the day, you get to
decide what feeling you want to send to
your homeowners based on how you dress.
But we have to get rid of the no-nos.
Cuz in my opinion, like people
will say, well, that's just.
I, I respect that.
I, I, I truly do respect people
to say, well, that's just me.
And at the same time I wish to challenge
folks who say that, to say, I understand
that it's just you, but how do you
strike that balance of being just
you, but also being received openly?
By the folks that that you wish to serve.
Because again, being just me, if I
smelled like cigarettes and booze and
garlic and I didn't dress, I didn't
wash myself, and I smelled like B, and
I had a sweaty stained hat on, and a
stained sweatshirt and ripped jeans
in my shoes with the laces untied.
If that's you.
Use you in your personal life,
but I would try to dial like
upscale you for your work life.
And I just want to air this
out cause I see it a lot.
Well that's just me.
So that being said, let's get in
right now to what not to wear.
First things first, what not
to wear branded apparel from.
Any brand name of your choice that's
spread across the chest, don't wear that.
If there's a logo on your clothes,
it needs to be your company logo.
Of course, a small little Nike or
Under Armour things a different
story, but I don't wanna see like
Hollister, Abercrombie, and Fitch.
Whatever brand that you wish to
broadcast to the world, that's casual
apparel does not have a place in the
workplace, and I know the workplace is
our customer's homes in this respect.
So get rid of the branded apparel.
All right, number two,
ripped tattered clothes.
I know that like it's, there's like the
style with the jeans, with the holes in
it and the ripping and all the things.
I, I personally find that that is,
Like a personal expression, style
piece, and I would recommend that
you not wear ripped clothes to work.
Okay.
Bringing me to number three, any
clothes that are stained, including
sweat stains, including hats,
which I'll talk about in a moment.
Get rid of 'em.
And I have my sweatshirt, my, my
branded sweatshirt with a hoodie.
when I was selling in Wisconsin,
for example, where the winters
get cold, it gets cold before the
winter, so I'm often bundled up
and I had my work jackets, I had my
sweatshirt and one of my sweatshirts,
which I loved, I wore one day.
It was disgusting out and I was like
helping the crew and I was carrying
some bundles and doing some cleanup and
everything Got gross and stained through
the stuff that was all over the place.
Cuz this happens, right?
Because we are in construction.
That sweatshirt I didn't even
realize I'd go to put it on.
I'm like, wow.
I, I literally look like I work in a
mechanic shop, which is no fault to
people who work in a mechanic shop.
That's not how we wanna present ourselves.
So if your clothes are stained,
old, sweat stained, tattered,
whatever, get rid of 'em.
Okay?
So there's purposefully
tattered, and then there's.
Beaten up and if they're
beaten up, ditch 'em.
All right, so that's what not to wear.
Outside that.
Let's go top to bottom.
Top hats yes or no.
My view today, if you
asked me, I'd say no.
But you're gonna say,
Adam, you're a hypocrite.
And the answer is not a hypocrite.
I just changed my views.
Go back, watch all the videos.
I'm wearing a hat and everything.
When I was selling a war hat all
the time, but I became a bit more
aware when my hat had a giant sweats.
Sheena was like, you gotta stop
filming videos with the roof
strategist hat with a sweats name.
It's gross.
So I tried washing it, still was stained.
Put it on a few days later.
Pure coincidence, I'm on a sales call.
Cameras aren't working.
We're shooting the breeze.
Leaderships tell me how.
Funny it is that their top salesperson
is running around with this gross, dingy
hat that they cannot wait to get off his
head cuz it's so stained and disgusting.
Meanwhile, I'm literally wearing
mine and I'm like, they can't
see cause the camera's not there.
And at that moment I was
like, wow, people notice.
And I just, it didn't really click to
me, you know, call me stupid by the way.
You can be like, ah, you're in sales.
You known this.
That's too blind to it.
I'm like, do people really care?
And the truth is they do.
They notice.
Even though I was blind to it.
So hats clean hat with a company
logo acceptable in your market.
Now let's move on to our
top half in Colorado.
This is like Colorado casual.
It's a flannel.
By the way, when I was in Wisconsin,
I did wear nice flannels tucked in.
Some people are gonna
say, that's ridiculous.
Why would you do that?
It worked in my market in Colorado.
I could get away with this.
I probably couldn't in a different market.
So is that my first choice?
And the answer is no.
My first choice is
company branded apparel.
You've seen me in my roof, ER shirts
in all my videos, and this is the
exact style of shirt that I was
wearing when I was in roofing sales.
When the.
Was here.
I could keep my pen in my
shirt, which is where I like it.
And these are a great, great apparel
piece when it comes to roofing sales.
Tuck your shirt in.
That's all I ask.
Just tuck it in.
You know, I'm wearing an over shirt right
now, which doesn't need to be tucked in.
And it was designed that way.
And it, it's a different style,
but these untucked just look
sloppy and like you didn't try.
All right.
Now when it came to, uh, higher end
communities, higher ticket sales,
multi-family sales, commercial.
Churches, things like that.
Multiple decision makers are more
often than not dressed up in a
button up with a collar shirt.
Alright, so there you
have it on your top half.
When it comes to sweatshirts, I
will always go with a little bit
more formal, although I know many
companies do use sweatshirts.
We are on the trades after
all, but sweatshirts so long
as they're clean and look good.
All right, let's move
down to your bottom half.
Jeans, khakis, chinos, shorts,
jeans, khakis, chino shorts.
Sounds like you're about to
like bust out a new song.
Um, which one do you do?
My opinion?
Anything but shorts.
The shorts, there's one exception to the.
If it is truly a Scorcher, if it's
110 degrees and you're out pounding
indoors in Texas in the middle of
summer, I think you get a pass down.
More often than not, I will do
everything I can to avoid shorts.
I don't think it sends a
super professional image.
Call me an old fashioned old man, if you
wish, but showing up with like your socks,
showing hairy legs, and it just doesn't,
it doesn't have that professionalism.
That I would wanna broadcast.
That's just me.
I do know that plenty of
people do wear shorts.
Plenty of folks are
gonna say, it's so hot.
You would change your mind if, and
let me just share this with you.
I used to work when I was in
college with the US Forest Service.
In Colorado when it was summer, which
gets really hot, and I was required
for safety to be in long sleeves and
long pants, and I was huffing through
the mountains carrying backpacks,
trekking 10 to 20 miles a day,
sweating and sweating and sweating.
So I do know how hot it can get.
I do know how annoying it is to be
covered up, and at the same time
I just, my preference is always
to jeans or khakis and chinos.
Goes into that one jeans, just make
sure that they look clean, presentable,
no rips, no tears, no bedazzling.
I know that people like
bedazzled stuff these days.
Uh, I would just leave that stuff
for the casual time and not in work.
Jeans, excuse me, khakis or Chinos.
That's up to you.
Some folks will.
You need to be in khakis or chinos.
I disagree.
We're in the trades.
Look like it.
All right.
If you show up wearing a three
piece suit to sell a roof, I'm
gonna be wondering how you're gonna
climb the ladder with those wing.
That's just my opinion.
Agree or disagree in the comments below.
So there's your bottom half.
Avoid shorts unless you have
that Brutal, brutal, brutal heat.
But I know that there's folks
that just like wearing shorts.
Uh, and, and that's okay.
All right.
Footwear, let's get down
to the bottom half here.
Footwear, what do you wear?
Truth, truth be told, pretty much
any shoe with a decent soul, whether
it's a trail runner, whether it's a
sneaker, whether it's a tennis shoe
or a a running shoe, are all gonna
have enough bite on a shingle once
you get to seven to eight, 12, or.
Always my, my recommendation is to
have a roof specific shoe such as
Cougar paws, and the reason is safety
and confidence and look and look in
the park, but forget that, that's
secondary to your safety and confidence.
If you're into the boot look and you
want, uh, I'm a big leather boot fan and.
Mock toe boots, specifically with a
wedge soul are gonna have good bite
and they'll have a, usually a, a steel,
uh, shank to help climbing ladders.
So you have a good firm press
and they don't collapse while
you're climbing that ladder.
I know you've probably had that happen.
If you're climb ladders and flimsy
shoes, your feet kind of fold over it.
So it's nice having like a mock toe,
like a a, if you wanna get nicer.
Boots like Red Wings, uh, classic
Mato or Thoroughgood, Mato.
You know, Dan makes the bull
run, I think, or the, with
the, with the Christie we soul.
So any of those wedge soul
boots look really sharp.
You can dress 'em up to be the elevated
work wear and they do well on roofs.
And again, if you have any other
contributions, drop a comment below.
So there you have it from top to bottom.
We've got our company branded
apparel or a button up.
We have it tucked in with a belt on
jeans, khakis, or chinos is just fine.
Avoid shorts.
And on your footwear you can go sneakers
or a work boot and again, a mock to boot.
And then keep your cougar
paws for the steep stuff hat.
Try to ditch it if you
need it, cuz the sun.
Just keep it branded, keep it clean.
And whatever you do, do not wear your
shirt you brought back from Cancun.
Any other company, branded apparel,
anything stained, stinky, or fatigued?
Get rid of it.
And the last thing I want to close.
How you show up in what you look
like is your choice of how you wish
to, to broadcast yourself, whether
you want to be more upscaled and
dressed up approachable and casual.
Whatever you do, so long as
you're clean and put together,
I don't think you can go wrong.
And remember, not everyone's gonna agree
with what you do, but you get to choose.
So for my attire, I am upscaled work wear.
That is my comfort zone that feels
like it matches who I am and broadcast
the right message of approachability,
being grounded and down to earth and
not trying this whole status play of
look at my fancy three piece suit and my
nice wingtip shoes and whatever it is.
Again, that's just my personal
opinion, so I'd love to hear from you.
What do you think?
The the items that you should wear.
And most importantly, what
should you absolutely not wear?
Drop a comment and share it with us.
That's what we love about this community.
So thanks for joining me on this video.
If you liked it and you want more,
jump into our free training center,
and if you want to just continue with
me right here, hop into this video,
I think you're really gonna like it,
and we'll see you on the next one.