Ask Allie: How to Make Wardrobe Classics Look Trendy

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I spend my days in a pretty casual office, where even the managers wear jeans and t-shirts, so my minuscule capsule wardrobe has remained something I use only for date night and visits to relatives. My company is sending me to the corporate HQ and I need to dress professionally.

I am blonde and my wardrobe staples are khaki. I love the idea of the fitted white oxford shirt and nice heels with my khaki staples. Problem is, when I have these clothes on I look professional, confident, put-together… and about 20 years older!! How can I wear the classics and still look like an up-and-coming star-employee of an edgy internet start-up company?

I think your question is one that many small wardrobe folks battle with. A wardrobe full of hard-working classics that mix and match with ease, but can feel a bit dowdy or boring, especially when dealing with creative types. However, there are many trendy and stylish people who have a similar wardrobe.  When you analyze the wardrobes of style icons you will see they too have a closet of classics, and they are usually in a neutral shade.  Here's a few examples of current-day style icons who wear very classic looks, and what they do to look current and fashionable.

gwenyth paltrow fashion
Gwyneth Paltrow – Fit

On the red carpet, Gwyneth Paltrow often wears very edgy and modern gowns. However off the red carpet, Paltrow is known for her very clean and classic wardrobe. She’s not one to wear a lot of color, accessories, or embellishments and doesn’t jump on every trend bandwagon. The way she makes her very basic wardrobe look modern and hip is by having a very keen eye for fit. Paltrow regularly wears slim pants, structured jackets with strong shoulders, and slim sheath dresses. Everything has been tailored to perfection to best flatter her lean frame. The slim silhouettes and perfectly hemmed trousers and skirts make classics look quite chic and very modern.

rachel bilson fashion
Rachel Bilson – Accessories

Rachel Bilson's look is young and fresh, but her personal style is surprisingly classic and simple. Over and over, she wears the same sort of silhouettes – styles that work now and would also work a couple years from now. Bilson keeps her personal style on-trend and covetable by adding accessories to the mix. She is known for bold booties with everything from skinny jeans to floaty frocks, looping colorful chunky scarves and pashminas at her throat come winter, and carrying a statement bag – be it a clutch or an oversized hobo. If you remove her jackets, bags, and shoes you will see her core wardrobe is quite timeless and simple. The addition of accessories adds edginess and a youthful vibe.

michelle obama fashion
Michelle Obama – Color

Michelle Obama will occasionally add current trends and edgy designers to her wardrobe, but in general her personal style is quite classic. What makes her stand out in a crowd and be seen as a style icon is her great use of color. The First Lady’s closet must look like a rainbow, for she hardly wears neutrals or pastels. Her silhouettes are usually classic – most often you will see her in ladylike full and pencil skirts paired with fitted blazers or cardigans or a classic sheath dress. However she doesn’t shy away from any color – from school bus yellow to fire engine red, FLOTUS has worn it and worn it well. For you, you can make it a signature color or colors to go with your khaki-based wardrobe staples.

kate moss fashion
Kate Moss – Defined Personal Style

Kate Moss is known as a fashionista, but when you break down her wardrobe, it’s quite simple. Moss has a uniform of a tiny dress or skinny jeans and trousers paired with a blazer. What makes it style icon-worthy is how her personal style is so clearly defined. Kate Moss loves rock and roll and it’s clear by who she marries, what social events she attends, and how she dresses. Her classic ivory pantsuit will have very square padded shoulders and be paired by platform high heels; a typical date night ensemble of little dress and blazer is made edgy with snakeskin print and satin lapels. Even for red carpet events, Moss chooses either short and sparkly, or long and flowing with a '70s vibe.  She keeps the color palette simple, the silhouettes classic with a rocker vibe, and shows her personal style with tiny touches that all add up to big fashion.

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  1. This is a great post and I LOVE how well you curated the collection by style icons.  It is so hard to imagine all the trends on our individual frames, but when you see the trends on the same person, side by side, it becomes a great visual of personal style.  I am definitely going to favorite this post!

  2. Great advice and breakdown–so easy to see how all of these ideas will work to bring some life into our most tried-and-true-and-boring basics.  Thanks!

  3. I like the idea of a white shirt with accent colors and the tan suits the writer already owns. A visit to HQ where you’ll be on display isn’t the time to be trying out an alternative personality, it’s a time to be shining for what you are. Start-ups may be edgy, but they’re about hard-working people busting their butts to make a difference.  

    Don’t be afraid to move beyond a button-down oxford blouse.  There are tons of lovely white blouses out there.  The far left pix of Ms, Paltrow shows a white shirt, perhaps a bit more open through the neck than you’d choose, that is stylish.  The 3/4 length sleeves are a little different and the material has a nice drape.  The Kate Moss photo on the left has a collared blouse, but she how she pairs it with low-slung pants so it’s not totally preppy.  

  4. I vote for being sparing with the belts also.  My only gripe with Mrs. Obama’s outfits is that she puts a belt on things I think might be best left alone. 

  5. I’d vote for the accessories and styling to make a khaki skirt and white shirt look more youthful. Maybe bright lipstick (hot pink? Orange/coral?), maybe a funky belt or necklace? Definitely add cool shoes (not comfy old lady shoes or even classic shoes. What about animal print? Or a pop of colour such as red patent?).

    Good luck and have fun.


    P.S. I bet you don’t really look 20 years older!

  6. FANTASTIC summary – I will be bookmarking this column for sure. I think a key element in looking youthful is your headliner – FIT. I see so many gorgeous young woman in suits that don’t fit them: pants dragging the ground, sleeves too long, jackets drowning their frame, pants and skirts that are too snug in odd places.  Ill-fitting clothes mean instant frump, and it makes you look non-descript too. Don”t just belt everything and hope for the best. if your clothes fit properly people will see YOU.

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