4 Outfit Ideas With Desk-to-Drinks Flexibility

Setting aside time to socialize after work during the week is hard enough, but when you throw in the prospect of changing your outfit into something more “festive,” it starts to sound like an absurdist fantasy. Running home in-between is often infeasible, and lugging around a “going out” top and impractical shoes can be a struggle in terms of both handbag capacity and early morning planning. Come to think of it, I’ve never been able to make that end-of-day sartorial swap transpire, no matter how hard I try (and this is coming from someone who works in an industry where acceptable office attire isn’t as strict as other, more corporate environments).

In hopes of determining a set of styling guidelines to tackle my transitional outfit woes, I challenged myself to intentionally dressing in a manner adaptable to both professional settings and post-work frolicking for four days. While my resulting takeaways weren’t groundbreaking hacks, they felt revelatory in the sense that they effectively codified an approach for crafting ensembles with day-to-night mileage. If you, too, remain consistently stumped by the prospect of transitioning your outfits from desk to drinks, scroll down for a handful of ideas.

Day 1

I love to mix patterns as much as the next maximalist, but when it comes to easily transition-able outfits, neutrals offer significantly more flexibility. A black- or white-based ensemble composed of simple, structured basics like a plain button-down and slacks is appropriate for almost any occasion. This approach also removes some of the laborious thought process often involved in crafting an outfit suited to multiple engagements; grab for the nearest neutrals in your closet, and you’ll probably be okay. If you do decide to add in some color or pattern, I would recommend opting for more tailored pieces to ground the statement in a typically office-appropriate silhouette (my floral vintage Dries Van Noten vest is a great example). In conclusion: neutrality results in flexibility.

Day 2

Speaking of vests, I found that easily removable, indoor-friendly layers are incredibly helpful components of good day-to-night ensembles. I say “indoor-friendly” layers specifically, because a coat or jacket you definitively plan to take off as soon as you get inside doesn’t really have an impact on the appearance of your overall outfit. Blazers, vests and even a light trench worn buttoned just at the top (like this one I’m wearing from Isabel Marant) make for great indoor-friendly options that you can take on or off depending on where you are and what you’re doing.

Day 3

I’m mentally kicking myself for all the times I decided to bring a change of shoes to work… inside an old tote bag. The irony that I consistently counteracted a stylistic choice with a decidedly unattractive one is not lost on me, however the solution is simple: packing my shoes in a bag I actually like! For a long time, I’ve associated bigger bags with practical utilitarianism because of their ability to hold numerous items, but that old prejudice is no match for the convincing slew of seriously cool big bags on the market right now, like the A.W.A.K.E. one I’m carrying here.

Day 4

Okay. Hear me out. I’m pretty sure bandanas are the ultimate accessory when it comes to surprising but delightful work- and play-appropriate ensembles. They’re less fussy than a statement necklace or silk scarf but still add an element of thoughtful put-together-ness that might otherwise be lacking. I’ll admit I discovered this revelatory fact entirely by accident when I was assembling an outfit around a white T-shirt, jeans and a black blazer that on their own might seem too boring or too casual but with a bandana? Instantly jaunty.

What self-enforced wisdom do you employ when dressing for both work and play? Tell me in the comments.

Photos by Waqas Farid. 

Anum Bashir

Anum Bashir is a third culture kid currently living in Dubai. She’s the Founder of Desert Mannequin, a podcast host, fashion and brand consultant, and co-creative director of NDUO. In her spare time, she eats cheeseburgers.

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