My Mom Says: Never Dress Better Than Your Boss!

And for men, the title is adjusted to: Do Not Drive a Better Car than Your Boss! 🙂

I’ve been asked many times by women what they should wear when going for medical interviews or those who wish to start a career in the healthcare field. Specifically, one of the most common questions are related to wearing Christian Louboutin shoes where there seems to be a split in opinions. I’m going to dedicate this post to my mother who’s taught me important life skills that most people would never teach you. The following are some tips for what I think is best to wear during important professional interviews, whether you’re going for medical residency, law school, or a CEO position. Of course, each person/case/scenario may vary, so you have to judge what is applicable to your situation.

Eg. Here is the general attire that I wore for my residency interview last year. I’m wearing RW&Co‘s skirt-suit (mind you that it has not been ironed since then, so the suit is wrinkled), H&M‘s blouse, and Jimmy Choo heels. For my actual interview, I had my hair up in a bun instead and wore nude pantyhose (do not go bare-legged!!!).


1. Stay conservative, traditional, and professional with your clothing:

Depending on what field exactly, I think women should wear a skirt-suit. If you’re not comfortable with the idea of a skirt for whatever reason, then trousers are fine as well. You have to be comfortable wearing your suit! Being comfortable with yourself shows honesty and exudes self-confidence which is the most important thing during an interview.

Does your suit need to match? I think that would be a good idea! If you’re not a runway model for Roland Mouret, then it’s best to match your top and bottom pieces.

Are colored suits okay? Only in the fashion industry, they may be acceptable, but I would even be cautious in this field. You will never go wrong with a black suit, but you can always make a fashion faux-pas! The medical field is always conservative. Speaking from my own experience, I thought my friend and I crossed the line when we wore our grey suits because we were THE ONLY TWO who wore non-black! As for other neutrals like brown and navy suits, meh…. I’m not keen on them and think they make me look old… but if they work for you, go ahead!

Is the length of my suit/skirt right? Do I need to get it tailored? It’s important to look good in a suit that fits you well. The length of the sleeves should be right at your first thumb knuckle (medically, first metacarpal-phalangeal joint) when you hang your arms straight down at the side. Your jacket’s length should hit you at your hips (the anterior superior iliac spine). Your skirt length can vary slight at the knees – slightly higher up if you’re short like me or traditionally right below the knees if you’re tall. If you have a large bust, go for a larger size suit and have a tailor nip in the sides and cut the sleeves. When you actually go for your interview, make sure to keep your blazer jacket buttoned-up!

Do I need to wear pantyhose??? YES for a formal interview! As granny-like as they are, pantyhose is a must for me! Choose a matte style with nude color that matches your skintone. If you prefer black, I would go for a sheer matte style with a denier count of less than 40.

2. “It’s the shoes that carry the woman” – by Christian Louboutin:

Okay, let’s address this Louboutin yes or no question. For me it’s a definite no if it’s for a very important interview. People know CLs are very expensive – so you don’t need this job then, right? Just try to imagine from the other perspective, if you were the interviewer and you have your interviewee in front wearing CL, how does that make you feel? If the interviewee dresses better than the interviewer, there is always the chance that people may think of you negatively for whatever reason. If the interviewer doesn’t care, then all the better, but why risk your chance? Not only so, they are a distraction from YOU! The interview should focus on your assets, skills, or other capabilities, and not your shopping style or fashion taste. I would be weary when some people tell you to act non-conservatively…

How high do you go? Less than 3 inches and never wear platforms.

What color? Neutral.

What style? Slightly pointed, round, or almond toes in work shoes are all fine. The classic is of course a point toe. No weird logo decorations on the shoes please and the only bow-like design that I think is acceptable would be Ferragamos.

Can I wear peep-toe styles? So I guess you don’t plan on wearing pantyhose either then? lol That’s a double no! Peep-toes have never been considered to be work appropriate in a conservative setting.

I can’t wear heels, are flats ok? I think most ballet-like flats are too informal. I prefer a pair of structured flat shoes.


3. What to do with you hair, makeup, and accessories:

How much accessories can I wear? The bare minimum. You only need your watch to be honest. I would say stick to a total of 3 SMALL pieces. You have a watch already, then choose 2 from the following: ring (if you’re married or engaged), earrings, or necklace. I think it’s inappropriate to wear “statement” pieces and even if you’re in the fashion industry, that cocktail ring that you have on may very well be viewed as something passé from 2 seasons ago.

Gold or silver jewelry? The timeless debate. I personally prefer gold even though I have pale skin. I think it has something to do with my grandmother liking gold more… However honestly, wear what you’re comfortable with. I have no opinion on this one other than NOT BOTH at the same time 🙂

What bag to bring with me? A small black logo-less tote is best.

What hairstyle? Conservative – wear your hair up in any style (ponytail, bun, or even slightly messy updo). Do not style your hair with bountiful waves. There were a couple of girls on my residency interview tour who had their hair so styled as if they’re going to prom. I think they were only missing some glitter…

What about my makeup? Conservative – this is not prom again.
The night before, give your face a moisturizing mask so that the next day your face will be ready for lights and action! Do NOT drink a lot of water before bed because this will give you puffy eyes the next morning!
My routine is that I like a matte foundation to even out my blotchy, tired skin from lack of sleep. Try to look “lit from within” so that you give a positive energy, but not with a shiny face. For all my important events, I wear Chanel’s Matte Lumière foundation which gives perfection to your complexion.
Your eyes should be a simple wash of neutrals – light brown, taupe, or grey (no red undertones please as this will make you look like you partied all night). No smoky eyes or harsh eyeliners!!! Add a bit of mascara and you should look beautiful. For me, I use La Prairie’s Luxe Caviar Eyelift Cream, then I add MAC’s Paintpot in Painterly to prolong the wear of my MAC eyeshadow in Satin Taupe. I’ve been wearing Lancôme’s Hypnôse mascara for the last 10 years now, so you can never go wrong with this in black!
You can add a bit of light pink blush and lipstick to complete your look. Do not wear lipgloss! Your shiny lips will be distracting!


2. Be professional in your speech, posture, and gestures.

Do not slouch. Not only do you get back fat from long-term slouching, your arms grow bigger too! I’ve always been taught to stand straight with your shoulders back, suck in your stomach, and tuck in your bum. This gives you a near perfect straight line.

Not only is the content of your speech important, so is the way you talk! Try to be professional. I always prepare a list of possible questions that people might ask me and I MEMORIZE my answers. Or at least practice in front of the mirror a couple of times to know how you look/act/speak.

For both my medical school and residency interviews I had an entire 20-30 something pages of notes typed up and had memorized every word. Usually for any situation, I’m always prepared and if you put your position in that of an interviewer, I’d say 99% of the time, you’d be able to figure out their questions. What they want to look for is how well you can portray YOURSELF in an overly generalized question. People want to see what type of person you are and if you fit in with the existing group of workers. A simple question like, “Tell me about your strengths and weaknesses” is not just you saying a couple of random adjectives and no one wants to hear “oh my weakness is that I work too hard.” My rule of thumb is that for every answer you provide, you MUST back it up with an example or two. Examples help people relate to you, stories draws people in, and blunt-ended answers close off connections which are crucial to form within that 15-20 minute interview (and if you’re good, they’ll want to keep asking you questions and keep you for maybe 30 minutes!). One of the the best advices given to me was to keep a story bank and the best ones are experiences that could be applied to several situations so that you can spin them around and don’t need to necessarily memorize 30 different events. You should have 10 good stories at hand to be used anytime. The more experienced you become, the better you will be to connect all the stories so that the interviewer does not forget them or if they didn’t completely get it the first time (and no one really does!) you’ll be able to connect the missing links and give them a whole view of yourself.

Lastly, if people ask you do you have anything to add or do you have any other questions? ALWAYS ask something insightful pertaining to their field (ie not so common that you can just look it up on the net), this shows that you’re genuinely interested! Do NOT ask about salary and benefits. You have not gotten the job yet. It’s a good idea to consult your family and ask them to interview you. Prepare your answers well. Then it’s just a matter of reciting them during the actual interview and people will be blown away by your thoughtful, comprehensive, and personalized answers.


3. Smile sincerely!

Please do not flirt. This is unprofessional. Do maintain good eye contact, smile sincerely, and enjoy your interview! Remember, you got here because people think you have potential and are genuinely interested in knowing you more! 🙂