A Tyba Guide to Dressing for Startup Success

Theodora Filip
Find a job that excites you.
5 min readFeb 19, 2015
The folks at Evernote redefine personal style on a daily basis.

PICKING OUT ANY OUTFIT to impress is challenging enough without having the pressure of landing your dream job breathing down your neck. You want your wardrobe to scream “I really want this job”, but you also want to steer away from looking like a fully-decked-out Christmas tree in the middle of August.

With the clock ticking away, and the interview getting closer, we tend to ask ourselves things like: Do I settle for the classic suit and tie look, or do I go for the more accessorized, “this is so me” ensemble?

Truth be told, walking into your interview dressed inadequately is a bit like showing up to a black-tie event dressed for the Halloween Party down the block. Bottom line: it’s not cool; it’s not cool at all.

Imagine this: You’ve rocked the application process like a boss and landed the interview (in which case, congrats my friend!). But as you wallow in the anticipation, excitement and nerves, one thought comes to mind: “It’s a startup”.

This is usually followed by the slightly more panicky questions of: “What do I wear?! Do I wear my jeans? A dress? Or maybe I’ll rock a turtleneck and channel my inner Steve Jobs…”. And, lastly: “What the F-word is smart casual, anyway?”.

A great example of how the Iphoria team members live and breath style.

First off, raise your hand up high and give yourself a big fat high-five if you actually know what dressing smart casual, business casual or startup casual even means. Personally, I don’t. To me these terms sound like a lot of mumbo-jumbo.

The ‘official dress code’ — the grey suit, the white button-down shirt and the black pencil skirt — are like extinct species when it comes to interviewing for a startup which pretty much leaves you with a hit-or-miss scenario.

Now, while some startup offices might be super cool with you showing up in a hoodie and jeans, others would much rather you channel your inner Olivia Pope and treat the interview room as your own personal catwalk.

This post is designed to help you tackle the dress code dilemma with some tips we’ve pulled together from our own experience. Hopefully, they’ll you avoid the faux pas and get you all dressed to impress instead!

Make sure you feel comfortable.

Dress for comfort, and add a sprinkle of style! Disclaimer: comfort ≠ wearing your favorite leopard-print Snuggie to the office. In fact, that thing should really never, ever, leave the safe confines of your house.

BUT, you should make sure that you feel comfortable with whatever you’re wearing when you walk into that office. At the end of the day, you need to make sure that whatever it is you decide to wear gives you enough breathing space to sit down comfortably without any wardrobe malfunctions.

When it comes to startups, personality and fit can be two of the biggest contributing factors to whether or not you get the job. And because startups tend to want to get the hiring process right from the get-go, the interview process can take up to four or five hours — especially if everyone on the team pitches in. So make sure that you are comfortable in your outer skin; leave the pumps, the 80s shoulder pads, and the too-tight-to-breath skirts at home and opt for something more flexible.

Remember: ‘Being comfortable’ can still mean being stylish; make sure to dress for the part.

Stalk the hell out of the company beforehand.

Startups usually take home the gold when it comes to creative company culture, unconventional work spaces and mind-boggling office art. Getting a grasp of the company’s culture can give you a headstart in picking the right outfit.

If you’re about to start working for a company that values attention to detail and makes looking good their business (sometimes literally), then adding some creativity into your attire and throwing on a statement necklace could help score you a home run.

The Treatwell team handling business.

Figuring out a company’s culture can be tricky, but don’t worry: we’ve got you. Go back to your startup’s Company Page or glance over their Facebook photos, engage in some harmless online stalking, and take note of what the team members are wearing. This will give you a behind-the-scenes look at office life and will help you plan your job-winning interview get-up.

You want your future employer to see that your style, and what you’re wearing, is in line with the ideology of the company. Dress for the job you want, but be careful not to go overboard.

Dealing with The Fashion Police.

Dressing-up for your startup interview can be a pain in the ass, especially when the dress code guidelines are an open book.

Efforts to pin down the dress code can go south pretty fast when you have smart-casual and business-casual terms popping up like wild mushrooms after a rainy day. It’s so easy to get it wrong.

You can wind up coming off way too smart, or looking so laid back you’re horizontal. If you end up on either of these extremes of the scale, you’re going to stick out like a sore thumb and get the wrong kind of attention. So our advice is that, when in doubt, settle for the dressier side — always.

Look at it this way; being over-dressed is always better because you can dress down (take off your tie or cumberbund), but if you show up looking way too casual and scrappy, you’ve already lost the battle.

Have anything to add to this story, or want to share a funny story about the time you interviewed in the right or wrong outfit? Share it in the comments below or holla at us!

Words: Theodora Filip

Originally published at blog.tyba.com on February 13, 2015.

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