Dressing for the Conference Room to the Cocktail Lounge

How to create the perfect workplace-to-weeknight outfit.

what to wear to work when you're going out after

As someone who works in an office that requires ties and eschews jeans, I often find myself challenged to develop a workplace-appropriate outfit that wouldn’t look out of place when meeting friends after work for a night on the town.

No one can deny the smart sophistication of a well-tailored business suit, crisp white shirt, and power tie, but you wouldn’t want your date thinking that you’re about to rise from the table to present a PowerPoint about financial projections for the upcoming fiscal year.

So what do you do when you have a client meeting at noon and a cocktail rendezvous at six? Packing a bag with “going out” clothes is an option, albeit a possibly clunky one. Embrace the challenge of creating an outfit appropriate for both contexts.

I’ve found the most success utilizing corporate colors with a contemporary attitude to find that versatile aesthetic appropriate for both the board room and the bar. As always, the fit should be trim and flattering.

men style what to wear to the office   tweed sport coat wingtip boots

The Base Element: Suiting Up

A suit or a sport jacket in dark, professional colors like charcoal and navy are universally safe with an interesting pattern like a herringbone tweed or subtle windowpane check. Pinstripes and chalk stripes are fine for the office, but their dressier association with businesswear wouldn’t deliver the desired effect for your night out. On the other hand, peak lapels can be considered too flashy so a standard notch-lapel, two-button suit jacket works for both contexts. (Learn more from Primer’s Visual Guide to Understanding Common Suit Features.)

With fall now upon us, you should have no problem finding the perfect tweedy jacket like this J. Crew’s Ludlow in herringbone English tweed for less than $300. (On sale for $208 with “GOSHOP” right now) Consider also this navy tweed sport coat from the more budget friendly Factory line from J.Crew for $114.

If you decide to forego a suit, find a pair of well-fitting trousers in medium or dark gray to coordinate with the jacket like these slim charcoal cotton-blend trousers from Banana Republic. In addition to being generally more comfortable than suit trousers, chinos are also easier to wash and maintain after a full day of wear. Andrew is wearing a pair from the Gap that they refer to as twill, but are more wool-like in texture, offering the effect of dress pants in a modern fit that works great outside of the office.

men's work outfit ideas   fashion inspiration

Sportcoat: J.Crew, $208 with “GOSHOP” (similar) / Pants: Gap, $42 with “FORYOU” / Wingtip boots: Stafford, $70 – Alt: Florsheim, $190 / Tie: The Tie Bar, $22 / Pocket square: The Tie Bar, $11

Adding Character: Shirt and Tie

Finding the right shirt may be the trickiest part of the outfit. Whites, light blues, and stripes are best for the office while darker colors and interesting patterns and textures look best for a night out.

Start with a light-colored shirt with a subtle pattern – not enough to distract during that 2 PM meeting but just enough to fit in at the 2 AM last call. Be sure that the shirt’s pattern doesn’t clash with any pattern in the jacket; it’s one thing to look interesting, it’s another to look chaotic. French cuffs are fun and classy at the office, but they can get in the way of a packed schedule so you can stick with traditional button cuffs.

This micro-grid slim fit shirt from Gap ($42 on sale) is both interesting and professional, plus the “zero wrinkle” smooth cotton weave should look just as good at the end of the night as it did when you buttoned it up in the morning. Budget-minded shoppers can give this similar shirt ($30) from Target’s new Goodfellow & Co. line a shot as well. (Check out Primer’s Fitting Room First Impressions to get our early takes on Goodfellow & Co.!)

A man wearing a suit and tie

Depending on where you're going after you clock out, you can ditch the tie to further dress the look down.

Feeling bolder? Look for a pattern like this sharktooth-printed cotton shirt from Banana Republic.

Ties are strictly enforced at my office, and I prefer to keep mine on after hours rather than stuffing it into my pocket. A solid-colored textured silk skinny tie, such as this 007-esque midnight navy piece from The Tie Bar, brings your outfit together with an understated panache that looks professional behind your desk and slick at the end of the bar.

A white pocket square with navy trim adds a subtle touch when “TV folded” in your breast pocket during the work day and when puffed out at night for some Tom Haverford-approved flair.

Read more from Primer about how your tie and pocket square should fit.

men casual outfit inspiration fashion denim jacket wingtip boots charcoal pants

With trim fitting pants and wingtip boots, simply dropping the jacket and tie in exchange for a dark denim jacket gives you an even more casual look without having to change in the office bathroom. Denim jacket: Levi's, $69

denim jacket with dress pants wingtip boots

Denim jacket: Levi's $69

banana republic shawl collar cardigan

Depending on your office requirements, you may be able to forgo the sportcoat for a shawl collar cardigan with the tie. Then at the end of the day, simply drop the tie. Shawl collar cardigan: Banana Republic, $70 (similar), Alternate: Gap, $48

Stepping Out

Your shoes are the finishing touch, and – since you’re expecting to be wearing them for quite a long day – you’ll want them to be comfortable and durable… in addition to looking good. Lace up a pair of versatile ankle boots in either black or brown to coordinate with your belt. In the photos, Andrew is wearing the Stafford Deacon from JCpenney, which isn't currently available (it comes and goes regularly). You can get a similar look from Florsheim for $190.  Or, these Delk waterproof leather chukka boots from Clarks will only set you back $100.

Does your workplace have a dress code? How do you dress for post-work social plans?

Nick Guzan

Nick Guzan is a public relations consultant and writer living in Pittsburgh. He blogs about men's style in movies and TV at BAMFStyle.com. His interests include old movies, muscle cars, maritime disasters, fast food, and single malt Scotch.