Going Biz Casual (Trad) 100% of the Time

[mrFurly]

Not exactly 100%...but I want to change my wardrobe completely around.


Ive been working from home the past 5 years, but now im going to be dealing with small business owners and doing a lot of networking (im in a pretty conservative industry).
Also...im 34, but look 23 (at least thats what people tell me).
So I want to look stylish, meanwhile project authority/trust.
I like the Trad look the most.


My question is...
...what should I have in my wardrobe that will have me ready for every situation?


As of right now, these are the things I know I need.

1. Pants.
Pants are something I cant thrift. But I dont know where to look or start.
I have 3 pair of J Crew wool trousers (Blue, Gray, Burgundy), and 1 Pair of Cotton J Crew trousers.
Past this, I have no idea which direction to go.

What else should I have? Types, brands, colors, etc... ?

Also...is there a special name for the cuff I see so many people on SF have on their pants? I really like that look.

2. Accessories.
Pocket squares, cuff links, socks, and whatever else I may be missing.

I guess this stuff is easy to find/choose. Ill probably just start with a simple linen white pocket square and slowly build from there.
I purchased some cheap socks from one of those online sock clubs...but after looking at the outfits on here, I can tell they are cheap and look cheap.
Cuff links...any recommended vendor? Ill probably end up just going on eBay to find them.



3. Sportcoats that arent blue/beige

I have a variety of blue/beige blazers & sportcoats for both summer and winter.
As well as a few tweeds.
What would your next choice be? A gray sportscoat? or something with a little more flare?


I think the above 3 points are my weak spots.

Is there anything else I should consider?

What I have...

6 Suits - navy, charcoal, and light gray

3 Brooks Bros suits (one is a beige summertime Brookscool I found).
HSM Gold Trumpeter
Saks Black Label
SuSu


30+ dress shirts of all colors...
From Brooks Brothers to Turnbull & Asser

10 pairs of AE shoes.

Selvedge denim, cashmere/merino sweaters, various coats, 20+ ties (mostly Brooks Brothers)


Any help would be much appreciated.
In this short time ive already become addicted to menswear.

 

[bigmoomoo]

Hopefully I can give you some general guidance, but there are a lot of questions there.
Quote: Generally grey trousers will be the most versatile. Material/weight depends a lot on your local weather. Most formal trousers will be in wool or a blend. You can also look at cotton/linen or other summer weight blends that you can cuff and press.

Quote:

They're just cuffed trousers. It was the style 10 years ago and is making a resurgence again recently (likely why you see it all over SF).

Accessories
Quote: That's a quick way to undersell an outfit. With all of your accessories you mentioned (cuff links, socks, etc), take a much more measured approach. In the beginning I found myself with way too many accessories and not enough staples to wear them with. Get a couple squares (on sale) that you love for the design, and then look to add more if you love them. For squares, conventional advice is to go for a bolder design/pattern with several colors to play off of, and not to directly match the tie (primary colors). I don't tend to see cuff links used much in a business casual setting.

 

[johng70]

You don't say what your role is in dealing with small business owners. Or what types of business owners. You don't want to overdress and look pretentious. Wearing links, blazers and pocket squares in the wrong situation can make you look like a pretentious douche. In other situations, it is just fine. It all depends on what your job actually is and what the small business owners you are dealing with are like. Don't mistake accessories and formality with looking professional. You can have a nice pair of slacks and button down shirt and be perfectly professional looking. The key is to have well fitting clothes - don't have pants an inch too long, or too baggy. Don't wear shirts too loose.

First impressions are important - in lots of situations, dealing with mom & pop shops - wearing a blazer with pocket square and cuff links will definitely give off the WRONG first impression.

I think, rather than debate hypothetical situations, if you provide us with what your job actually is and the types of small businesses you are dealing with we can give you better advice as to what mode of dress might be more appropriate.

 

[mrFurly]

Good point.

I sell commercial insurance.
So the types of people/businesses I see will vary...from mom and pop shops, to very formal corporate environments.

Most of the time I can get away w/ business casual because im in the office.
Also, as we all know...in today's world most people are casual at all times anyway.
but, im in Chicago...which tends to lean more conservative when it comes to business attire.
Most men I see are wearing a sloppy looking suit w/ no tie.

I just want to be prepared for all situations.
With my age, and how young I look, I think it will be better if I'm slightly overdressed.
The insurance industry is older. The average age for a broker is about 48 (most I come across are 55+).

 

[thesilentist]

Fellow Chicagoan here. I think the above advice for not getting carried away with accessories is smart. Honestly, I wouldn't even wear a pocket square if I was in your situation.

A few key points:

1.) Dark colors/tones. Apply this toward sport coats, suits and trousers. It's going to seem so boring, but a navy jacket and mid-grey to charcoal trousers with dark brown or black shoes is your friend.

2.) Want to bring in color or a pattern? Then consider doing this in your shirt only. Avoid super colorful shirt/tie/pocketsquare/socks combos. Way too over the top. Save that for a party.

3.) Make your clothing less memorable, but well-fitted. You want the business owners thinking about what you're offering, not being impressed by your wardrobe.

To me, there's a big difference in dressing for "fun" and then dressing for work in a business-to-business environment. Especially when you're dealing with small business owners. You want to immediately establish trust with your appearance, not that you enjoy shopping. I know this sounds so entirely boring, but that's kind of the point.

As for cufflinks, I like vintage art-deco style ones. Or I wear ones I received as a gift from family or friends. I don't own very many, and I own even fewer French cuff shirts. And I think that wearing French cuffs with anything other than a suit doesn't work. If you're attempting to go business casual, I wouldn't say French cuffs fall under that category as it's more formal.

For clients I meet with to help build their work wardrobe, the focus is almost universally on understatement. Most of them either bring in color/pattern with either their shirt or tie -- never both. I've discovered there are "tie guys", "shirt guys", and guys who haven't realized they should pick between those two for the office.

If you want to look older, then dress more on the conservative spectrum.

 

[mrFurly]

Fellow Chicagoan here. I think the above advice for not getting carried away with accessories is smart. Honestly, I wouldn't even wear a pocket square if I was in your situation.

A few key points:

1.) Dark colors/tones. Apply this toward sport coats, suits and trousers. It's going to seem so boring, but a navy jacket and mid-grey to charcoal trousers with dark brown or black shoes is your friend.

2.) Want to bring in color or a pattern? Then consider doing this in your shirt only. Avoid super colorful shirt/tie/pocketsquare/socks combos. Way too over the top. Save that for a party.

3.) Make your clothing less memorable, but well-fitted. You want the business owners thinking about what you're offering, not being impressed by your wardrobe.

To me, there's a big difference in dressing for "fun" and then dressing for work in a business-to-business environment. Especially when you're dealing with small business owners. You want to immediately establish trust with your appearance, not that you enjoy shopping. I know this sounds so entirely boring, but that's kind of the point.

As for cufflinks, I like vintage art-deco style ones. Or I wear ones I received as a gift from family or friends. I don't own very many, and I own even fewer French cuff shirts. And I think that wearing French cuffs with anything other than a suit doesn't work. If you're attempting to go business casual, I wouldn't say French cuffs fall under that category as it's more formal.

For clients I meet with to help build their work wardrobe, the focus is almost universally on understatement. Most of them either bring in color/pattern with either their shirt or tie -- never both. I've discovered there are "tie guys", "shirt guys", and guys who haven't realized they should pick between those two for the office.

If you want to look older, then dress more on the conservative spectrum.

gotcha...keep it presidential.

Learning about workplace norms is super interesting to me.
Ive never been in this type of environment.

When I first met with the company im going to be working for (prior to reading anything about clothes)...I went with the intention of it just being a conversation about the industry, so I just wore a gingham shirt tucked into some slacks.
Thankfully the owner is a casual kind of guy...and we hit it off...
....but he made a comment about my shirt having a pattern, and he told me he knew I wasnt a corporate guy as soon as he saw me.

That comment made me really think about my dress, and all of the social norms I wasnt privy to.

Are tweed jackets OK?

 

[mensimageconsultant]

Tweed jackets would be safer with small businesses than corporate environments.

If there's a need for vision correction, conservative glasses help create a more mature look.

 

[mrFurly]

If there's a need for vision correction, conservative glasses help create a more mature look.

hmmm....didnt think about that.
Glad you said it because im probably going to get a pair of new frames this week.