Style Scenario: First Day at Work – Laid Back

What are you going to wear? Sometimes it’s good to look at a few suggestions then add your own tweaks and ideas. That’s what these are for. Seemingly hand-in-hand with the advent of the digital workplace, came the laid-back dress code. Jeans are aplenty, and suits are becoming increasingly rare. Still, with many office places housing a diverse set of employees in multiple business units with different priorities, it’s important to look put together and sharp if you reside in the more relaxed crowd of business. Or, if you’re a work from home employee or self-employed, this can serve as a guide to staying comfortable, yet putting you in a state of mind for work. As a former work-from-home professional, I know the difficulty of productivity when you spend the whole day in gym clothes.

The Sweater: Goodthreads Cotton Shawl Cardigan – $40. One of my New Year’s style resolutions is to wear more green; blue’s less-loved but almost equally versatile and diverse brother. This pick is a basic from Amazon’s “Goodthreads” brand, but with a ton of really positive reviews, it should serve you well. Want something a bit different but still perfect for this outfit? Try this very much on sale Lambswool bomber from J. Crew. 

The Pants: Banana Republic Rapid Movement Denim Athletic Fit – $70.80 when 40% off ($118). I have NEVER been the type of person to spend more than $40 for a pair of denim. Then, these happened. A true revelation. Just the right amount of stretch for even the most thunderous of thighs for the #LegDay crowd, and a smart taper that keeps things modern without being skin-tight. 

The Henley: J.Crew Double Knit Henley in Heather Stone –$53.99 ($59.50). J.Crew is a hot mess right now, but that shouldn’t stop you from scouring their site and stores for deals. Perhaps BECAUSE of the ongoing turmoil and desperation to recapture sales growth, mega discounting seems to be the new norm. The almighty Henley is one of the items J.Crew does consistently well, is often on sale, and adds more masculine complexity to this look than a humble T-shirt can. UPDATE: Was just on mega sale, but now pretty close to full retail. Amazon’s Goodthreads to the rescue!!

The Belt: GAP Basic Leather Belt in Brown – $28 ($40). Old faithful. I can’t think of a time this belt hasn’t served me well, from suit and tie to jeans and a sweater. Basics like this are ideal for building a wardrobe on a budget. The polished rectangle buckle adds some pop to an understated accessory, combined with genuine leather and lasting durability make it a winner. I’ve worn mine 3-4 times a week since 2016, and it’s still going strong.

The Shoes: Adidas Stan Smith White/Blue- $80. Longtime fans of the Stan Smith will tell you the leather quality, comfort, and versatility are why the shoe has been popular for decades. Those same fans will tell you that these use to be much cheaper, but even at a full price of $80, you won’t regret owning a pair.

The Watch: Hamilton Khaki Field Automatic Black Dial- $369. If a casual office setting is in your foreseeable future, this may be the only watch you ever need. Beloved by neophytes and watch snobs alike, the Hamilton Field Khaki Auto is built to take a beating and looks great in almost any setting. Buying a watch online for the first time? Take a look here at a rundown of your different options, and the pros and cons of each.

The Socks: Express Solid Heel Stripe Socks – 4 for $25. Lighter colored socks with a nice striped pattern play well with the sneakers in this outfit, without going over the top with the print.

Want to see some other style scenarios for a first day at work? Head here for the first day at a dressed up office. Then here for a smart casual place of work.

About the Author: Jason P. is a Dappered devotee, having curated the majority of his wardrobe through the site. He is an enthusiast of wool sweaters, chino pants, and affordable automatic watches. In his free time, you can find him at his boxing gym or antiquing with his wife