So things are going great, and now you both can’t wait til the weekend to see each other.

Weeknight dates give you something to look forward to after a long day at work. But there’s a tiny problem…

What happens when you don’t have time to go home to change?

What the hell do you wear to work that doesn’t scream “I just came from work” when you show up to your date!?!?!

Today I got you covered.

BUT FIRST, TO THOSE WITH STRICT DRESS CODES

Now, before we jump into some strategies, I want to give you a bit of a warning:

If you have to wear a uniform to work, or are bound by strict “suit & tie only” rules, you might need to bring a change of clothes. (Don’t worry, none of these tips require you to tie your tie while looking in the rearview mirror.)

FOR THOSE JOBS ON THE BUSINESS CASUAL/CASUAL SIDE OF THINGS

If you got some wardrobe flexibility on the job, here are 5 strategies I show my private styling clients to seamlessly go from work to date night.

Casual Dinner Date Outfit Idea for Men
Blue Suede Trucker Jacket by Todd Snyder | Button-Down Shirt by Bonobos | Chinos by Bonobos | Socks by Uniqlo | Leather Desert Boots by Thursday Boots

TIP #1: AIM FOR SLIGHTLY OVERDRESSED

For When You Both Want to Try That New Vietnamese Place Every Can’t Stop Talking About

Even if you work at a casual office, aiming for slightly overdressed kills two birds with one stone.

  1. You look ready for work, and
  2. You look like you’ve tried hard for your date (effort = attractive)

A trick I teach my clients is to use The Swap Trick to upgrade just one item in an outfit.

All you have to do is start with an outfit you’d normally wear, then swap one casual item for something a bit dressed up.

The simplest swap you can make for that “Instant Upgrade”: wear a button-down shirt in place of your usual t-shirt. A collared shirt instantly signals “I’m trying a little bit harder”.

Some more examples include:

Happy Hour Cocktail Outfit Idea for Men
Tailored Double Breasted Topcoat by Mr. P | Cashmere Sweater by Theory | Slim Fit Black Jeans by Rag & Bone | Socks by Pantherella | Contrast Sole Derby by Want Les Essentials

TIP #2: MIX CASUAL AND FORMAL PIECES

For Post Work Happy Hour Cocktails

Another trick is to balance your outfits formality by making sure you mix casual items with ones on the dressier side. This balance helps you avoid that “I just got off work” look.

Black denim is a great secret weapon for work to date outfits. Its darkness helps it fly under the radar in the office, but helps you feel a little more relaxed at a nice bar that isn’t so fancy. (Just don’t make the mistake of going for destroyed denim).

Balance out the casualness of denim by opting for leather dress shoes instead of sneakers, and a tailored topcoat instead of something casual like a bomber jacket.

Insuring your outfit has a nice blend of casual and formal pieces helps you hit that sweet spot of effortlessly sharp.


Low Key Concert Date Outfit Idea for Men
Leather Bomber by Golden Bear | Cotton Cashmere Sweater by Todd Snyder | Weekday Warrior Pants by Bonobos | Socks by Uniqlo | Olive Suede Chelsea Boots by Thursday Boots

TIP #3: REMEMBER THE RULE “MORE DETAILS = MORE CASUAL”

To See That One Band You Both Bonded Over

A good rule of thumb to remember: the more details something has, the more casual it is.

For example, a graphic t-shirt is more casual than a solid color t-shirt.

A striped shirt is a bit more casual than a solid shirt.

A destroyed pair of jeans is more casual than a solid blue pair of denim.

Using this concept, we can easily make something casual like a leather jacket be work appropriate by opting for a design void of excess zippers, snaps, and details, like this sleek brown leather bomber.

Activity Date Outfit Idea for Men
Black Satin Bomber by Bonobos | Slub Linen Polo by Onia | Weekday Warrior Pants by Bonobos | Socks by Pantherella | White Sneakers by Greats

TIP #4: LOOK FOR PIECES THAT BLEND FORMAL DESIGN AND CASUAL COMFORT

For That Activity Date Cause You’re Both Avoiding Alcohol Right Now

Dressier clothes don’t have to be stuffy. Advancements in design have helped brands add some much-needed comfort to a lot of your standard office clothes. So look out for pieces that look traditional, but have comfort features like stretch, wrinkle resistance, and breathability.

One of my favorite pants right now is Bonobos Weekday Warriors, which made from stretch easy care cotton. They’re as comfortable as sweatpants, but make you look sharp.

Pair them with a solid breathable polo, technical bomber, and clean, minimal white sneakers and you’ll be ready to go from your team meeting to an activity date without breaking a sweat.

Fancy Dinner Date Outfit Idea Men
Suit by Mr. P | Wool Rollneck Sweater by Paul Smith | Merino Socks by Falke | Leather Loafers by Tricker’s

TIP #5: DARKER COLORS MAKE YOU LOOK SERIOUS AT WORK AND SEXY ON A DATE

For That Fancy Prix Fixe Dinner

So you got some real post-work dinner plans, the kind that of place that mentions “jacket required” when you made reservations.

You got a classic charcoal grey suit, and wearing a collared shirt and tie makes you feel like you’re ready for a job interview, not a romantic dinner.

My fix? Dress it down with a turtleneck (Remember tip #2, mix casual and formal!).

The key here is to use this as an opportunity to add a bit of color to that grey suit. My suggestion? A maroon, which pairs well with grey.

Going for an overall darker color palette for this outfit makes you look like you’re in serious mode for work. And once you sit down to the mood lighting at dinner, you’ll officially activate sexy mode.

TO RECAP

  1. Aim on the dressier side Use “Instant Upgrades” like a collared shirt in place of a t-shirt and boots instead of sneakers to elevate your date night look.
  2. Mix casual and formal pieces Making sure your outfit has a nice blend of casual and formal pieces helps you avoid the “I just came from work” vibe on your date. If you’re wearing dress pants, pair it with clean minimal sneakers. If you decide on a t-shirt and jeans, pair it with a tailored coat and boots.
  3. More details = More casual If you’re unsure if a casual piece is appropriate for work, follow this rule. The more details a piece has, the more casual it is. So if you want to wear a t-shirt to work, make sure it’s a solid t-shirt and not something with a graphic on it. Same goes for denim – go for a solid blue pair instead of one that’s distressed and destroyed.
  4. Look for classic designs made with modern tech Clothes with stretch can help you look ready for an important meeting, but help you feel relaxed on a date.
  5. Add darker colors to your date night outfit Office attire can be an endless sea of grey. Your date will appreciate a shot of color – just make sure you pick something on a the darker side, in a nice maroon instead of a bright red. Going for something a bit darker not only keeps things a bit more conservative for your job, it also makes you look sexier under date night mood lighting.

NEED SOME MORE DATENIGHT TIPS?

Check out this post where I asked 101 women what a man should wear on a first date!

peter@theessentialman.com'
Author

Hi, I'm Peter. I spent 11 years as a menswear designer here in NYC. Now, I help some of the most successful men look really good as a Private Personal Stylist and writer of The Essential Man. You can learn more about what I do by clicking here