In many ways, the first day of a new job is similar to the first day of school. It’s exciting and fun, but it can also be scary and overwhelming. No matter how you slice it, people are judging you, and it only takes a few seconds to make an impression. To get started on the right foot, you need to look confident and comfortable, and your clothes play a key role, sending an instant message about who you are.

Panicking yet? Don’t worry! I’m going to share some tips to help make that first day a fashion success!

Here are my suggestions on what to wear on the first day of a new job.

Do your research

The job interview is your chance to get to know your future employer, but it’s also a good opportunity to see what people in the workplace are wearing. Is it a t-shirt and jeans crowd? Are you working with fashionistas? Try to glean as much as you can, and don’t be shy to ask you hiring manager. When in doubt, it’s best to be a little overdressed, so leave behind the jeans and tee! You can always adjust your wardrobe as needed if it ends up being a more casual environment.

Even if you’re overdressed, the idea is to look understated and professional –you want to be remembered for your work and skills, not that you wore a crazy outfit!

What men should wear

Overall, it’s a good idea stay away from clothing that’s too trendy your first day – it’s not the time to sport that “grey patched and destroyed sweater” by Yeezy. A good suggestion is a tailored suit in a dark hue like navy or gray, with a pop of colour in your shirt or tie (something subtle – unless you want to be known as the guy that wore a pastel tie).

If a suit is not required, opt for a tailored dress shirt and pants.

If you go this route, I’d recommend leaning on classic fashion staples that every professional should have in their wardrobe: button down shirts in solid colours, chinos, crewnecks, and jumpers. They’re called classics for a reason: they don’t go out of style.


In general, stay away from shiny fabrics and “silly” ties. You want to look professional. On that note, it’s vital to make sure your clothes are ironed! There should be no stains or rips either, and pants should be hemmed properly. I always suggest taking your suits to a tailor. it’s well worth the investment and you carry yourself better when something fits perfectly. The last thing you want to do is end up looking sloppy, which definitely sends the wrong message to your boss and co-workers.

The shoes

Shoes are a key factor in your first day look – this is not the time to sport your sneakers. A classic leather dress shoe in black or chocolate brown always looks sharp and classic, just make sure they are clean and polished.

What women should wear

For women, I would opt to keep it simple – think of an icon like Audrey Hepburn when choosing your look. A black sheath dress, or tailored black ankle pants with a crisp white button-down and tailored blazer (with classic pumps) are the kind of looks you should be striving for.

Typically, it’s a good idea to keep your hemlines appropriate for the office, meaning no miniskirts or skin tight dresses. You can play with trends a little bit but don’t sport anything over the top; remember you are trying to make a good impression.

A good rule of thumb is if it’s something you would wear to a nightclub, then it’s definitely not for your first day of work. Even if you want to be stylish and trendy, it’s important to always look understated and professional. A chic scarf and a few delicate bracelets are great added touches, but I’d advise against sky-high heels in fuchsia or a giant statement necklace.

Sarah Jessica Parker

The shoes

Similarly, you should look to keep your footwear simple. The office is not the place to sport your stilettos or over the knee boots. Instead, I love a classic pump in black or nude, and if you don’t wear heels you can opt for a simple ballet flat in a neutral colour. Keep in mind that the first day on the job is not a great time to break in a pair of new shoes; if they’re uncomfortable you will look and feel uncomfortable.

Clothes make the (wo)man

Remember that details matter, and it’s often the simple things that pull your look together: a fresh haircut, manicured nails, and a classic makeup look (no hot pink lipstick or sparkly eye shadow!). You might be equating your first day with a fresh start, but it’s maybe not the best time to try out a new trendy hairstyle or makeup look. Make sure you try everything on and that you feel great in your outfit. Have it all set, ironed, and laid out so that the morning of you will not have that stress hanging over you. Your outfit should empower you to do your best and feel your best!

Whether it is a fabulous pair of shoes or a head-to-toe outfit that you feel amazing, make sure you pick something that gives you the confidence you need. Confidence is essential for success, and your clothes help communicate that to your superiors and peers. It will shine through.

Good luck!

About Natalie Sexton

Natalie Sexton is a fashion stylist, professional makeup artist, and blogger. For more than a decade, Natalie’s passion for fashion and all things girly have been the driving force behind her Canadian-made brand of “Sexton in the City” Makeup, Clothing & Accessories. She can be seen regularly on CTV’s THE MARILYN DENIS SHOW, where she breaks down the latest fashion trends for viewers. For more information on Natalie Sexton, visit You can also follow Natalie on Twitter @SextonNTheCity.

*Images via Natalie Sexton Pinterest*