Best way to go from very casual to business attire?

[Nooch]

I work in a very relaxed workplace (I'm wearing shorts, a t-shirt, and a hoodie at the moment) and am pursuing a second career in Real Estate. The long and short of it is that I need to try and strike a balance between both worlds so I can be comfortable at my day job, but be able to dress up what I'm wearing enough to go and handle whatever business might come up after hours.

Is there a way to strike a balance (or rather, how would *you* strike the balance) between not looking too out of place at your day job (dressing nice will certainly get the 'what, you have an interview today or something?' comment), while looking like you fit in at your night job, other than 'keep a suit in the car at all times.'

Thanks!

[echelon_john]

Not Dockers.

Don't look like a salesman.

Depends on the market/demographics/psychographics, of course.

Details matter-nice belt, nice shoes, tasteful watch. Nice portfolio (Filson?) Tough to go wrong with nice/sporty khakis (Bill's, MTN Khakis, maybe others), a nice colorful pressed dress shirt (Ledbury, Tytwhitt, even Lands End or Bean)

No tie IMO. Blue blazer if it's not too hot; get it tailored.

All that said, this may not reflect your personal style at all. Still, if you nail the belt/shoes/watch/accessories, you could probably do nice jeans and a non-preppy dress shirt, say dark blue, grey, or black.

[Nathanrtaylor]

How out of place would cotton chinos and a polo shirt look at your day job? Keep a lightweight navy blazer in the car.

Depending on where you are in the country you have an entire summer to get your day job used to seeing you in chinos and polos. Then when you switch to oxford cloth button downs this fall it won't be as much of a shock.

Does the real estate gig really require a suit?

[Matthew Strongin]

I work at a tech company and over the course of a week my attire ranges from "hanging with developers" to "meeting with execs." I generally wear slim/fitted chinos and casual oxford shirts in solid colors. Untucked with vans and I'm pretty close to how I dress in my real life. If I tuck in my shirt and throw on a sportcoat I'm ready for most situations. Swap out the vans for oxfords and there are few work situations I'm not appropriate for. It gives me a wide range without changing the bulk of what I'm wearing.

[Nooch]

How out of place would cotton chinos and a polo shirt look at your day job? Keep a lightweight navy blazer in the car.

Depending on where you are in the country you have an entire summer to get your day job used to seeing you in chinos and polos. Then when you switch to oxford cloth button downs this fall it won't be as much of a shock.

Does the real estate gig really require a suit?

Ah, I forgot to mention location. I'm in Bergen County New Jersey -- my managing broker mentioned if you're playing under $500k, business casual is fine, but anything over and you're going to want to be presenting yourself in a suit. Thing is, it's totally unpredictable -- it'll be a while before I've established what kind of clientele I'll be dealing with.

You only see khakis and polos in my office if you're going out on a client visit, really. I've been thinking about bringing back the Express 'Producer' pants that I'd worn back at my previous company -- but I feel they don't pair well with just a t-shirt and sneakers.

[christian]

In summer: Flat front cotton chinos in British tan, brown leather belt, brown penny loafers, blue oxford cloth button-down collar shirt. This is casual attire. It's literally half a step up from jeans and converse. Our fathers cut the lawn wearing this. If you really want to flip it, keep the shirt tucked out at the office and wear Jack Purcells. Then tuck in the shirt and put on leather shoes when you leave the office. The uniqlo oxford shirt is surprisingly decent and cheap.

In fall: When it starts to cool down, you can add a v-neck sweater, and a Baracuta G9 Harrington jacket (in beige or navy) for your office and a navy blazer with brown horn buttons for your real estate clients.

In winter: Flat front wool whipcord trousers in dark gray, brown leather belt, brown oxfords, blue oxford cloth button-down collar shirt. Add a navy blazer or Herringbone tweed jacket for meeting clients.

Summer Nooch:
j-crew-shirt_400.jpg

Look, it's fall Nooch:
steve_mcqueen.jpg

[christian]

My answer is the same as Matthew Strongin's fwiw.

[pdmtong]

If you are over dressed, people don't comment. they expect you to look professional.

if you are under dressed, it hurts your brand.

never be under dressed. even if it means 5 minutes twirling in a bathroom stall. dress at the level of the clientele you expect to have. always. if you can tuck it in and throw on a coat and change shoes, sure fine. But I suspect to service the clientele you expect to have you will be doing a full superman in a stall.

[Nathanrtaylor]

Summer Nooch:
j-crew-shirt_400.jpg

Look, it's fall Nooch:
steve_mcqueen.jpg

Man. Summer was haaaaard on Nooch :-)

[Matthew Strongin]

Summer Nooch:
j-crew-shirt_400.jpg

That's pretty much what I'm wearing now, minus the hair. Works great in a modern business environment that tends towards casual.

[Nooch]

Man I need to flatten my stomach, lol.

Let me say, by no means am I afraid to twirl around in a bathroom stall -- I do it when I (seldomly) ride to work, and I do it currently to a few nights a week to go wait tables (I'm a hustler...)

That said, I don't necessarily have the bank roll at the moment to fund a spare suit for the car, nor do I think they'll keep real well under those circumstances.

But, more khakis and casual oxfords at work -- I can get down with that. Which I can step up in a pinch if I have an quick evening appointment -- ties are easy to keep all over the place, after all.

Let's talk shoes, for a second. I like boots, but 1) it's soon to be summer and 2) without going through the massive boots thread, what are some boots that might be suit appropriate, and some shoes that toe the line on both -- within a reasonable budget.. My current go to with khakis is a Rockport 'Office Essentials' Ellingwood

Additionally I've been trying to follow Chase's wardrobe on a budget plan and picked up some cardigans from uniqlo, and a whole bunch of solid grey/blue/black t-shirts..

[Vlad Luskin]

snip:

... but be able to dress up what I'm wearing enough to go and handle whatever business might come up after hours.

Depends on what kind of "business" you are looking for after hours.

;-)

[Nooch]

Getting back to this -- your preference on khakis and shoes, guys?

[Britishbane]

I do a lot of JCrew chino's (cause they make 'em long not because they're a good value - they're not) and quoddy bluchers.

[christian]

If you're trying to do this on the reasonably cheap, I would:

Men's Classic Penny Loafers | Free Shipping at L.L.Bean (in Cordovan, not black)
Men's Dress Chino Belt | Free Shipping at L.L.Bean
Men's Double L Chinos, Classic Fit Plain Front | Free Shipping at L.L.Bean (in Dark Khaki)

and

Men's Traditional Fit Doeskin Blazer from Lands' End (this is actually very very decent for the price).

All told, that's cheaper than a pair of Quoddy's. Which are awesome, but not cheap, nor dressy enough for sales.

[christian]

BTW, I subscribe to the theory that men have it easy - we can adopt the uniform of our forefathers and we will always be appropriately dressed. But I also believe that there is very little room for humor and irony in men's wardrobes; we are not children. Therefore my suggestions tend toward the more conservative.

[mjbabcock]

BTW, I subscribe to the theory that men have it easy - we can adopt the uniform of our forefathers and we will always be appropriately dressed. But I also believe that there is very little room for humor and irony in men's wardrobes; we are not children. Therefore my suggestions tend toward the more conservative.

I for one really appreciate the advice. Thanks

[nahtnoj]

Men's Classic Penny Loafers | Free Shipping at L.L.Bean[/url] (in Cordovan, not black)

These are an exceptional value for the money. Probably $50 cheaper than they should be.

[happycampyer]

BTW, I subscribe to the theory that men have it easy - we can adopt the uniform of our forefathers and we will always be appropriately dressed. But I also believe that there is very little room for humor and irony in men's wardrobes; we are not children. Therefore my suggestions tend toward the more conservative.

I suppose it depends on ones forefathers...

[jonathanb]

Go to Men's Warehouse and buy a suit as well as a couple of shirts and ties and keep them stashed in a suit bag in the car. You're less likely to find one outfit appropriate for both casual and dressy work environments than you are to find a frame that works well as both a gravel bike and an aero race bike.