20 Wardrobe Staples Worth Re-Investing In For Timeless Style

Hello, Gorgeous!

I have a habit of decluttering a little too hard, because lately I have only been purchasing items to survive the season when I really need it.

Now settled into an apartment that has more space, I only want to wear what is worth keeping and re-purchasing. I love wearing items to death, but also never want to get bored. Timeless style is different for everyone and should NEVER be boring.

Rebuilding my wardrobe includes styles with

Good quality
Wearable pieces with intentional use
My personality actually considered

This way I do not have to donate bags of clothes every few months to friends and worry about storage.

It weighs on my mind and causes me stress when I own too many pieces, so I like to – not keep it minimal – but reduce decision fatigue and make my life easy. Consequently, you can choose to blend in and be invisible yet polished or stand out depending on demand.

Here are 20 wardrobe staples worth re-investing in over and over again if you really love the styles and find use for them.

Disclaimer: My lifestyle might look completely different to yours, so keep this in mind when building your personal uniform.

You never have to only adhere to basic garments. Remember you are a dynamic woman with events to attend and a calendar of fabulous adventures out.

wardrobe staples every elegant woman needs

The list to start with:

Basics

Underwear
Socks
Loungewear
Activewear

Tops

Good everyday shirts
Polos
Sweaters / cardigans

Bottoms

Mini skorts
Tailored shorts
Tailored trousers over jeans: why they win every time

Outerwear

Utility jackets / technicals
Trench coat
Wool maxi coat

Dresses

Gowns over day dresses

Shoes & Accessories

Shoes
Bags
Timepiece

Optional Accessories

Uniform Jewellery
Sunglasses
Hat

Underwear: make your basics not so basic

On a day to day basis, flesh-tone seamless underwear are my go-to, but I am finding them to be granny. You can switch up the colour, print, or cut.

Since I am updating everything in my wardrobe, I shifted towards black bikini styles, because they are comfortable yet flattering when I see myself dressing up. It feels more glamorous and intentional when I am donning a cotton bikini, because it is more my personality.

Also, all my underwear is finally falling apart after I stocked up at least 3 months worth of underwear so I never have to think. It has been a good few months of watching them fall apart and lose elasticity.

I find it annoying to choose colourful underwear, but have a separate part of my dresser where the spicy exciting ones are stored. It never matters the brand, as long as you have a material you find comfortable and it looks dazzling on you.

You have to love it above all, so wear in secret what your heart fancies. I simply go to Amazon, but have been branching out to several brands for different reasons and moods.

Socks: have fun with not so secret surprises

As a runner, I quite literally run through socks. BUT this is changing, because I have always loved expressing myself through hosiery. It seems odd, but an interesting colour or cut of tights can add a heap of flair to your outfit.

Still stocking up on a lifetime of thick cotton running socks under my knee high boots and trainers, I appreciate calf-high and knee high tights under a pair of heels and mini skirt.

It is a highly inappropriate fashion statement, but I like the irreverence when on a day of shopping with my girlfriends from time to time.

I try to avoid fishnets, but I used to wear colourful wide cut pairs underneath my jeans 7 years ago. They are a fun surprise for myself, but I never really revealed this before. Bright neon blues change your mood.

Loungewear: relax in true comfort

Cotton-modal and jersey blends are the best for having dance parties in the kitchen and accidentally falling asleep on the sofa. This is why GAP and GAP Factory are my go-to for lounge essentials.

Doubling as pajamas, I feel like an expensive person when preparing coffee and breaking up boxes to recycle.

After splurging on a handful of basics, I realised how often I reach for them. Every YouTube video I post makes me look lazy, but I thoroughly enjoy repeating these outfits. They breathe life into your basics with comfort and a smart look.

Find your colour season, stick to it, and always look like a million bucks when meal prepping. The styles I have are so chic that I could wear the tops out with basic bottoms and a stainless steel watch. I look like I run a company in a movie haha.

Branching out, I am looking into varying brands as Eberjay, Intimissimi, and Negative Underwear for more elevated styles and hues.

A light hint for future hauls incoming. But first, I must add more holes into the ones I currently own.

Activewear: you can go polished or fun

I do not believe in wearing only a sports bra when working out because of the potential wardrobe malfunctions. To add to that, I already get enough attention when wearing a giant sweatshirt and loose fitted workout trousers.

Expanding into influencer territory, I have been looking at activewear that is not tight, avoiding yoga pants and cycling shorts. (They make me look like a turkey squeezed with string even as a size XS and after sizing up.)

Loose running shorts make me feel more comfortable and I like the length to be mid-thigh when out in public. I wear a sports bra underneath a loose cotton shirt that is 10 years old for support and breathability, but have been getting a better sweat with sweatshirts.

Giant sweatshirts it is for me. Adding a sense of fun with bright colours and feminine flavour make it look like I inserted effort. Especially since I simply reuse the same sweatshirt over and over until it gets really stinky.

I thought I am going to get stinky and sweaty anyway, so it does not matter. But it is not hygienic and makes me itchy before I shower. It is time to alternate and have a rotation–even with my cotton shirt underneath.

Shirts: good for everyday dressing throughout the seasons

Switch up the material from cotton to linen depending on where you are in the climate. I never owned linen shirts before, so this is a first for me. I used to only wear predominantly cotton whites and blues, but it is time for a change.

I get bored so fast, so I really need to upgrade smartly. The clever look of a shirt is so sexy when you can roll up sleeves, bear it over a crop or tank top in the heat, or sport it alone.

Style never ends with a good shirt, and I am having fun with this refined look for Summer. Obviously, you can layer it in the colder months.

I have never had more fun with sophisticated casual dressing by adding a long sleeve and collar. Moving on from silk shirts, this looks more relaxed outside the office and feels more deliberate.

Think a leather braided belt with good hardware, tailored shorts, jeans on a cold day, or crisp trousers. You could be on a yacht, at a sporting match, picking fruit, or boarding a flight.

If I saw someone in this look, I could probably ask them tips on how to max out my 401k. It whispers, ‘I have my life together.’

Polos: don’t overthink casual day occasions

Long live the polo! If you cannot handle a chukker mallet, that is perfectly fine. Equestrian boots are not included, but it is an easy look to commit to without staring at your closet for half the morning.

I get tons of compliments and comments from strangers asking what I do for a living or am treated with better manners. It makes that much of a difference when you have a collar.

Never overthink it. Own shades you love and look good in. If you are finding yourself wearing and washing it too much – find other brands.

I prefer to go to Ralph Lauren for a wide selection of preppy pigments and cuts. But Tommy Hilfiger is also a more affordable option to find neutrals you want to start with. Lacoste? Why not?

Do not limit yourself with one brand, because you might find another that suits your figure and lifestyle better.

Sweaters or cardigans: find your layer

I have a proclivity for cardigans, because my broad shoulders make me look like I am going to dance the Monster Mash as Frankenstein’s monster in a blazer.

Zip or button, cardigans break up the lines of your shoulders to look softer yet dapper when layered in a flattering way. I used to do the sideways knot over a shirt, because I am not always trying to look like my family donated a wing to [insert boarding school/institution here].

They also open in the middle which is a big plus when the sun changes its mind and a gust of wind rolls around. It is not as heavy or hot as a city jacket and easier to have on hand during a day trip.

Mini skorts: appropriate underwear that lets legs breathe

I love skorts. Standing at 5’2”–micro minis are better for my frame as they look proportionate. If they are slightly too long, I look like I am a Catholic school student which I am not. It is not the look I am going for.

Skorts are easy, because simple cuts make you look refined without your underwear showing if you sit without adjusting or bend over because papers flew out of your bag in the wind.

They look great styled with all the aforementioned garments above along without walking around in panties because of the heat.

Tailored shorts: because cut-offs make you look like trailer trash

There is a time and place for everything. But not for cut-off denim shorts. Some might like to use them as a coverup on the beach, but I prefer macramé or mesh draperies over cut materials.

You can even wear a shirt or dress over your bikini. Anything but cut-offs.

Tailored shorts are your friend no matter the length, because you will always feel like you have your life together, so you act accordingly. This is not a pygmalion effect but truly living your dream life.

Want to look expensive? Do expensive things that create expensive opportunities such as tailoring your shorts. Simple.

Tailored trousers: why they win over jeans every time

Jeans are fabulous as I have 2 pairs that every woman needs: a white pair and dark denim. If you are not a cowgirl or work on a farm–there is not really a need for them.

Anywhere you go, they tend to soak in all the stink and gather all the fragrance stronger than other fibres and look sad faster when wearing them a couple times.

Though I look great in a low rise cut, you can never go wrong in a perfectly tailored pair of wool, silk, or viscose trousers. They make everyone else around you want to dress up and sit straight when you wear them.

Tailored wool also protects with an extra layer for biting, wet weather.

I love how they are becoming more casually accepted as one of the latest trends. They suit everyone and are effortlessly chic matching all the designs iterated.

Utility & technical jackets: functional with good breeding

Don’t come from pedigree? Create your own. Leave the stylish legacy of accomplishing things that grandchildren will look at how grandma got things done. Dressing for your future grandkids is a flex.

I like to look to the late HM Queen Elizabeth II for queues on technical dressing and explorers also related to the Royal Family as Ranulph Fiennes. Whatever they are wearing to survive the freezing summits, long horse rides, and torrential downpours will literally last you centuries.

I love city jackets, but have been cutting down on them by having my utility coats double as them. Meaning Barbour wax coats, Holland Cooper fleece, and Helly Hansen shell layers because they prevent you from getting sick and are stylishly civilised.

It is worth saving for and finding them secondhand, because they last forever and make you look like an expert in fields such as hunting, skiing, or commuting.

They are perfect for everyday with pockets to hide items from robbers and carrying all your important items close to your chest. Nobody will want to mess with you because it is not too dressed up and you will be as capable as you look.

Trench coat: own one in every cut & colour that suits you

One cannot tell if it is the trench coat that stops me or me that stops for the trench coat. I always pause when finding a trench coat to feel the insides and look at the materials. Water repellent? Yes please.

Once in Denmark, I was warned to bring a brolly for the night. I did not like the California idiot I am assuming precipitation would be as consistent in Los Angeles. Only to find out my trench coat was not water resistant.

I was soaked and came home to shower off the cold after hanging my clothes to dry. I do not stand by making the same mistake twice, so I made certain my outerwear is consistent with functionality.

I love a good maxi trench coat to cover head to toe solely for keeping dry and healthy. Short ones look soooo good with a belt for a put together look. You will never look or feel stupid for having a trench to protect you whilst looking like writing an important paper or being a field messenger in World War I.

Aside: my love for the trench coat

A woman and I passed Burberry in a mall and she asked what I thought of the brand. Some might think of football hooligans in tartan. Others might contemplate Daniel Lee breathing life back onto the Runway. I think of something else entirely.

Blood spilt in trenches of ascended hell. Mud, flooded rainwater, bullets, and debris. All for the freedom of people. That is what I think of the trench coat: history and heritage. God bless the descendants of those men. Their courage will always be in our hearts.

Wool maxi coats: the search never ends

As I lived through 122 seasons of life so far, I have learnt that you can never have too many wool coats.

Winter feels long and hard, so you have to keep up morale by stocking throughout the year during off-season sales. You are a better woman for it.

Change the lapel, the breasting, the buttons, the cut, the collar, the print, the lining. Find a dégrader of all the gradients in between shades.

Do it for your health, your style, your cognizance. It is not only about sound wellness, but remembering who you are under a pile of layers. You are a lady and your coat should express it.

Gowns over day dresses: hear me out

I used to live in sundresses in Los Angeles only to whittle my repertoire down to a handful. They are lovely on absolutely everyone–so this is only me. After living in shirts and skorts, I find the utility to make more sense in my lifestyle.

Aside: men’s tailoring with a feminine touch

It is a recurring pattern in my styling that I tend to opt for menswear tailored to me, because I will always have a somewhat tomboyish taste I could never get rid of. Always a tad envious of what men look good in, I have a competitive streak in me when it comes to showing men how it is done.

Anything he can do I can do better. In heels, of course.

I do not believe in competing with men at all as a whole. I simply cannot resist the tailoring that originated all the looks we have today. They all stem from menswear. Even tunics and dresses.

When it comes to dresses, I now only shop for gowns for certain affairs in the coming season. They have to be over the top to mark the occasion, so I will only shop for less than a handful at a time.

I used to overcrowd my storage with too many evening silhouettes that never saw the moonlight.

Currently, I will find a few that make sense, ruminate, then take the plunge with 2-3 gowns a haul. Take them to the tailor and use the heck out of them with each of my social circles. Rinse and repeat.

There will always be a gathering to look forward to.

Shoes: one for every season you are on this earth

It is needless to justify a good pair of shoes. Life is short. Bring yourself the necessity of joy.

As I say this aloud, it pains me that I held back on buying good shoes. I started again, because I had no pairs for particular occasions. Initially, I thought I only needed a couple everyday pairs that take you from sunlight to sunset, but this is not good for my soul.

The variety really does make sense for my lifestyle since I love going out and switching up my style.

Bags: your outfits should be fun

Even when you are out conquering the world, you should manage to find a sense of form along with function. If your outfits can be as monotonous as mine on a regular basis, bags will give you sanity.

The seasons really fought me on this one and I carried a Winter bag in the sun. I am also finding totes with a zip to be exceptionally useful to not have my belongings fall out when acting like Lewis Hamilton in traffic.

Have fun. Go ham. Do not lose your soul limiting yourself to a minimal amount of bags.

Timepiece: actually check the time and only the time

Living life to the fullest is a matter of not having disruption for your phone. Yes, avoid an Apple Watch unless you are tracking your heart rate, sugar, sleep, etc. But have a day to day watch to get you through life that feels like a proper piece of jewellery.

Start with a watch that takes you from day to night in stainless steel.
Add to your baby collection with an evening watch that looks like a diamond on a hill,
then have a sporty watch for banging about on the beach in a fun colour, and so on.

I like my day timepieces to have more practicality that shares my personality reminding me who I am – so I found Casio to be the God tier of all these uses mentioned.

They have a flying instrument watch, boating watch, war watch, diving watch, dress watch, fun watch. All pretty affordable.

The question is: what do they not have? I am in love with most of them.

Casio is great quality for their worth when starting a watch collection. Start small. Do it for you.

Uniform jewellery: it goes with & uplights everything

When I say uniform jewellery – it could be one piece you cannot live without. For me, it’s earrings, because they do not get in the way. I have gel x extension nails and long hair for that.

For some, it might be a couple to a few pieces. My best friend has forever bracelets, because her tiny wrists cannot waste another day adjusting links. They are gold so they pass metal detectors with no issues. (It also depends on how detectors are tuned.)

Jewellery ties your outfit together with a feminine touch that makes you look even more polished. You thought of every single detail. Even on a hike or to the grocery store. I start my day with hoops and end with them. They are a part of me.

Sunglasses: necessary eye protection

I used to think sunglasses were a nuisance until my eyes became accustomed to my nocturnal schedule. They also help when driving during sunset hours, so I started having similar silhouettes readily available at my entryway and in my car.

Instead of digging for one pair, I have comparable flattering shapes in different brands that always look good. Protect your eyes. They are precious.

Hats: there when you need them

It helps to hats them neutral if you do not reach for them often and do not want to stand out. For instance, at the airport, going out for a grocery run on a windy day, or as an alternative to sunglasses on a sunny day. You can really let your outfit speak for itself.

However, you can really showcase your outfit or essentials for the season with a statement piece. I love letting my head breathe and making sure my hair does not go flat, so visors might be an option to avoid hat hair. Do not forget sunhats with a tie that can dangle around your neck.

Not necessary in every scenario, but you should have one in case conditions change.

Luxurious dressing: a considered wardrobe creates ease within daily robing

Ease is luxury. Intentional staples reduce stress, supporting a refined personal uniform. Every piece should earn its place through wear, function, alignment with your lifestyle.

If you are ready to build a wardrobe that feels intentional, elevated, and effortless every single day, join TheItGirlSchool.com.

Inside, you will learn how to refine your style and create a personal uniform that works for every version of your life. Step into your most polished era and start dressing like the main character of your own story.

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