How to dress with confidence after a career break By Sally Smy – Personal Stylist

Learning how to dress with confidence is a vital part of getting yourself prepared and key to a smooth transition. Your image is an important part of your personal brand and how you present yourself sends a message to your colleagues whether you are conscious of it or not.

Stepping back into the workplace after a career break can be challenging from a sartorial point of view. If you haven’t been in a work environment for a while, knowing what to wear can seem like a daunting task especially as current dress codes are far from straightforward.

The chances are it will have been a while since you updated your work wardrobe. Lack of time to shop, body shape changes and feeling out of touch with current trends are just some of the challenges faced that can make the task seem overwhelming. Please be reassured that you DO NOT have to be size 10, perfectly made-up or dressed in the latest trends. Just be the best version of yourself you can be. This does require some planning, time and effort but the results will be well worth it. The good news is that taking control of your image is empowering and will boost your confidence at a time when you need it most.

Here are some simple steps you can take to dress with confidence and create a winning work style

Consider the role you are looking for

The clothes you choose to wear need to take into account your goals, aspirations and lifestyle. If you are looking for a senior position then how you dress should reflect this. Research the dress codes of the organisations you are interested in at the interview stage and if you’re not sure, check with their HR departments. If you are setting up your own business, consider how you would like to be perceived by clients.

Look at what’s in your wardrobe

Don’t be tempted to dig out your old suit that is lurking in the back of your wardrobe. Chances are, if it’s been a while since you wore it, it will be out of date even if it does fit you! Go through everything you have that is appropriate for work and give your self an honest appraisal of whether it fits, flatters and most importantly how you feel when wearing it. If you can find a friend you trust to do this with you then even better. You should be left only with items you love and that make you feel good.

Work out your personal style

At this stage don’t be tempted to run to the high street and panic buy. With a bit more preparation and thought you will avoid a stressful shopping trip. Start by working out the shapes, colours and styles that flatter your body shape as this immediately reduces the amount you have to choose from. Then move onto the styles you enjoy wearing, for example if you love wearing dresses then look for one or two suitable dresses first. Having a few but well chosen items is key to simplifying your wardrobe and developing your signature style. Get some visual inspiration by looking at online brands, Instagram, and fashion blogs to build a mood board of styles you like. Pinterest is useful for this as it really does help to have an image in mind before you hit the shops

Write a list of what you need

Once you have gone through the first three steps it will be much easier to focus on just what you need. I would suggest limiting yourself to between six and ten items to avoid becoming overwhelmed. Identify the styles and brands you like and take time to research items online first. Once you have done this, make a plan for a shopping trip and stick to it. This way you’ll be far less likely to wander aimlessly into the crockery department! I do hours of online research and planning for each client before I even hit the shops.

Remember it’s not just about the clothes 

Grooming plays an important part in your overall image. Ensure hair and nails are clean and tidy and your footwear is in a good condition. There is no point spending time and money on your clothes and learning how to dress with confidence if you have scuffed shoes and dirty hair. Also, a little make-up can mask a thousand hours of missed sleep! I would advise booking a free consultation at a make-up counter if you need a refresh.

About the company:

Transition Peak Limited™ is an online career coaching and training portal that helps companies and individuals move forward and faster following redundancy, retirement or return. Our online programs provide access to tutorials, documents and checklists. We also connect individuals with some of the best career transition coaches and experts in the UK. The coaches and experts can provide workshops, group or one-to-one coaching. Find out more on

Was this useful?

Sign up now for your complimentary sample of our Career Transition Program.

For your staff going through redundancy, preparing for retirement, or returning to work after extended leave. Transition Peak can help with these transitions in life.

About the Author

Catherine Oliver - Parental Support Specialist
Sally SmyPersonal Stylist
Sally is a personal stylist and a founder at Queen Bee Styling. She helps individuals achieve a wardrobe that gives them confidence and to feel fabulous in the clothes they wear every day. Sally had a successful 18 year career in fashion buying working for leading high street retailers. She also runs workshops, talks and webinars about image and impact , personal branding and other topics. Visit our coaches page to find out more about Sally.