Swapping Dressed Up and Dressed Down Looks

Dress Up or Dress Down?

Everyone knows the famed fable of Dr. Jekyll and Mr. Hyde: An esteemed scientist and a gentleman who transforms into his criminal alter ego to indulge in his vices undetected. Wait, so how does this relate to men’s fashion? Well we aren’t asking you to be inspired by Dr. Jekyll’s criminal motives, but rather his ability to seamlessly transition from a gentleman to rugged bad boy and apply it to your way of dress. In today’s hectic work-life balance, swapping formal and casual looks on the fly becomes an invaluable asset in everyday life. Dress up for work, dress down for casual.

The key to versatile looks is having versatile clothing. Accumulate simple pieces without too many patterns and layer them accordingly so that you can add and remove pieces depending on the situation you are in. With layers, overdressing will never be a problem again as you can remove the necessary clothing to fit any occasion. We’re here to teach you how to set up your on-the-go wardrobe and what pieces to have in it to keep you looking sharp.

Dress Up/Down Procedure

There are two ways to go about this:

1. You travel to work in casual/activewear, change into businesswear at work, and possibly swap back, depending on the events of that night.
2. You travel to work in businesswear and possibly swap back, depending on the events of that night.

Whichever path you select depends on your lifestyle. For example, if you exercise in the mornings on your way to work or just prefer to dress in a suit exclusively at work, then follow Option 1. If you are a certified city slicker and have nightly events lined up, go with Option 2.

Regardless of the option, we highly recommend you keep a “side closet” in your workplace, which should house an assortment of spare items for your clothing rotation pre or post-work, with none more important than the white dress shirt (more on that later).

If you’re not at work but instead travelling to different events, say an afternoon coffee followed by an evening gala, then it is imperative to have a travel bag with you to carry all your belongings. More stylish than used grocery bags and definitely stores more, it’s a must for every man.

Workplace Closet Essentials

Business Attire (Even if you arrive in a suit, it’s nice to have backup in case you spill coffee on yourself)

White dress shirts: Shirts, as in plural. Three is a safe bet: One to change into, one as insurance, and one for mental stability in case the other two are already used. A white shirt is the pinnacle of a dressed up formal look, from business to events, and business events! Open collar for dressed down, though always with a pocket square. Bow tie for dressed up. Necktie for everything in between.

Navy blazer and dress pants: Why blue? Well because it’s bolder than that drab gray you see everywhere.

Solid color tie: Either a completely solid tie or a conservative pattern only, such as a red and blue argyle. Ideally it should fit well with any suit color that it is paired with.

Brown oxford shoes + matching belt: The “white dress shirt” of shoes, brown oxfords match any suit and should be the only shoes you change into when you arrive at work. Matching belt is a must.

White silk pocket square: A necessity that is often seen as an option, stand out from the crowd with a simple white pocket square. It’s amazing how something so small can make such a big difference.

Casual Wear

(Because it’s not cool to dress in a suit for pickup basketball. You’re not the coach.)

V-Neck sweater: Once you ditch the blazer after work, don’t leave your white shirt exposed and grab yourself a knit top. A V-neck sweater is a wonderful layering piece as it adds a degree of formality to any outfit but still keeps things casual because, well it’s a knit. Look for one with a lightweight merino wool blend and ideally a color you would have on a blazer. Still gotta look sharp, ya know?

Cardigan: The other knit alternative to your blazer, a cardigan is another wonderful piece to add to your dressed-down collection. The buttons provide a nice contrast to the knit material and is a bit dressier, though still holds its own as a dressed down substitution for a blazer. The material itself can vary by season, with either a fine wool for spring/summer or a heavier knit material for the colder months.

Knit tie: A casual alternative to your everyday work tie, the texture of the tie follows the ironic mantra of menswear: The more patterned or textured something is, the more it is considered dressed down.

Leather jacket: Not exclusive to motorcycle fanatics, a leather jacket instantly adds a badass look to your wardrobe. Ideal for the weekend warrior, though you don’t need to go rushing out to buy a Harley.

Jeans with contrast stitching: My guilty pleasure: A pair of dark wash jeans with bright rust stitching. They provide a simple, dark base with a subtle bit of detailing, just enough to catch the eye. From the most laidback of get-togethers to borderline smart casual.

Bright polo: Invite a pop of color into your wardrobe for more leisurely outings. Coral pinks, mango oranges, azure blue or tropical green are all wonderful choices.

Chinos: Go wonderfully with a dress shirt-cardigan comb or with just a polo, chinos are always welcome to the party.

Sneakers: Comfortable and forever young, sneakers are fantastic to get you from work and back but can also be the finishing touch for a t-shirt-jeans combo.

Loafers: Occasionally labelled incorrectly as “grandpa shoes”, loafers mix classy with a bit of Sunday morning brunch, which you can’t go wrong with. These are the middle-of-the-line shoes when a function is too formal for sneakers and too casual for dress shoes.

We get it, not everyone needs, or even wants to have a separate closet away from home. Of course you’re welcome to show up and leave work in the same suit and Armageddon can wait another day. However, as mentioned before, it can be an invaluable insurance policy when life throws you a curveball called “cottage getaway, leaving tonight”. Don’t be that guy in the suit at a cottage getaway, man. Can’t say we didn’t warn you.

How Do You Like To Alternate Your Looks?

We’ve showed you how to swap your looks to adjust to any situation. Clark Kent couldn’t change costumes faster than this and could only look half as good.

So how do you like to keep people guessing? Let us know in the comments below!