I frequently help clients evolve their styles into retired life. How their styles change varies from person to person. Some change their style drastically when they move into retirement, and others don’t change nearly as much. Either way, a lot of the preparation is the same and some things are universal. Here are some general guidelines on how to move your styles into the next chapter of your life.

Slow Down Dressy Career Wear Purchases

If you wear business formal or casual attire to work, or a work uniform of sorts, slow down the purchasing of that type of dress code a year to two before you retire. For example, purchase fewer formal sheath dresses, dressy suits, formal blazers, and high-heeled pumps and boots. 

Amp Up Crossover Items

Crossover wardrobe items are the pieces that you can wear in your non-retired and retired life. For example classic knitwear, smart casual outerwear, moto jackets, some blazers, some blouses, shirts, some pairs of trousers, dressy jeans, boots, tube skirts, ruanas, casual dresses, dressy flats and knitted tops are versatile items that can be dressed up or down. If you purchase more before you retire, you can dress them down with items like fashion sneakers, a utility jacket, jeans, utility pants, a denim jacket and casual boots in your post-work life.

Needs Analysis and Closet Edit

Once you’ve retired, a new needs analysis is in order because some of the factors that impact your style will have changed. You’ll need to do a few thorough closet edits in order to decide what to do with the work clothes, footwear and accessories you will seldom wear. Don’t pass it all on right away, and be sure to keep the crossover items.

Take Your Time

No matter how much you prepare and plan your evolved look for retired life, it will take time to find your stride. Try to make changes gradually and organically. Relax into it and enjoy the process. After all, you’re retired! Ideally, you need to settle into retired life for a while first in order to correctly establish new routines, schedules and activities, all of which will impact how you dress from day to day. Take your time to evolve your retired look so that you do it effectively, efficiently, and enjoy the results.

Build Effective Wardrobe Capsules

Once you have established routines in your new way of life, figure out which activity capsules you’ll need to complement them. All of my retired clients have fleshed out their activiewear, loungewear, casual wear and travel capsules. But some of them have also added athleisure, resort, cabin, beach, crafting, camping, gardening and theatre capsules to their wardrobe.

Build each activity capsule with mix-and-match items. Remember to incorporate existing wardrobe items into the capsules. You might find that you need to flesh out wardrobe categories like jeans, utility pants, athleisure bottoms, sneakers, knitted tops, casual skirts and dresses, house shoes, and casual toppers.

You also need to figure out your at-home style. Do you want to wear loungewear, athleisure, beach wear, casual wear, smart casual wear, dressier items, or a bit of everything. It’s all good as long as it makes you happy and works for your new lifestyle.

Hair, Make-Up, Nails, and Eyewear Re-evaluation

Re-evaluate your hairstyle, and the time and money it takes to maintain it. You might want to keep it the same, go grey, change the colour, leave it curly, go shorter, grow it out longer, add rainbow locks, straighten the waves, have it styled more or less frequently, or go for a more adventurous look.

Re-evaluate your nail care regimen. Do you want to amp up or scale down professional manicures and pedicures. Maybe you want to join Team Naked Nails. Maybe you want to have professionally groomed nails and feet because you finally have the time and can enjoy the results. Maybe things stay just the same.

Re-evaluate your eyewear. Maybe you want to switch from contacts lenses to specs, update your collection of readers, get prescription sunnies, or refresh your existing day-to-day eyewear. As for make-up, decide on a look that feels right day to day. It might mean wearing less than you used to, or keeping things the same.

Throw in LOTS of Personality

Your style into retired life needn’t be less fun, less expressive, or less visually impactful than before, unless of course, that’s exactly how you want your style to evolve.

Some of my clients are having even more fun with their styles after retirement because they feel less inhibited and more empowered. They can finally wear exactly what they want. Many are more sartorially adventurous and on-trend than they used to be. Some have maintained their daily levels of dressiness, playfulness, polish, tough edge, and avant-garde integrity. They continue to have fun with fashion, but are not bossed around by it.

Over the years, I’ve seen some of our veteran forum members evolve their styles into retired life, and they have never looked better. Your style might be different as you head into retirement, but it needn’t be void of verve, chic, and personality. Retirement can absolutely be your time to shine. You’ve earned it.

Don’t Leave Things for Good

I can’t stress this point enough. My late Mum, who loved to wear beautiful dressy clothes and jewellery, left too much of it for good. She died at age 59, and missed many opportunities. Wear your fabulous wardrobe items. If not now, when?

These guidelines are not exhaustive. Feel free to add your tips and experiences in the comments. I’m sure we can all learn from each other.