Let's Play Dress Up | Style Essentials - Jeanne Oliver

At the beginning of the course, I spoke of the difference between fashion & style.  We’ve discussed the most essential element to your style wardrobe is confidence! Having said that, I’d love to go ahead & share a few essentials.  As I researched & prepared for this course, certain items appeared over & over again in the “must have” categories and I’d love to share those with you.  Below I’ll list just a few of my personal faves!

Please know that my heart is not all consumed with high-end designer pieces and acting as if spending loads of money is the norm.  The closets in our home are full, and for that I am grateful.  But they are not full of couture and expensive, full price pieces.  I’m not trying to be anything I’m not. I’m not a young, rich, fashion blogger nor am I trying to be.  This is completely all for fun.  I’ve researched both ends of the spectrum for you and would love to share. For every high end skin cream or expensive designer piece, there is an affordable one to be found. Please have fun with this.  Let these “must haves” and tips not leave you frustrated but inspired. Okay. Now that I’ve gotten all that out of the way, let’s have fun with this!

“Never use the word “cheap”. Today everybody can look chic in inexpensive clothes (the rich buy them too). There is good clothing design on every level today. You can be the chicest thing in the world in a T-shirt and jeans — it’s up to you.”
Karl Lagerfeld





The most simple of all fashion pieces has become almost overwhelming, taking on a life of its own. Here’s the skinny.  Find a pair of jeans that fits you & stick with them, no matter the brand.  I’ve told myself if I can lose 10 pounds I’ll treat myself to a pair of True Religions. But truth be told, while I’ve heard they’re miracle workers, I have no idea if they’ll fit me perfectly or not.

You can find guidelines for choosing jeans but here’s a few things to remember.

  1. Not all jeans fit everyone. Just because they’re expensive or trendy does not mean they’ll work for everyone.
  2. Try a jean with some stretch. White & black jeans are a fun way to add a little spunk to your wardrobe.


Here are a couple links for you as you style according to your body type:




Hourglass:  If you are an hourglass, a classic, wide-legged trouser with a mid-rise and flat front will keep you looking slim in all the right places—but still show off your sexy curves.
7 For All Mankind High Waist Slim Denim Trouser in Atlantic Twilight Wash, $169

Pear-shaped:  Pear-shaped girls with curvier hips should steer clear of anything super-tapered and go for a low-rise flare or trouser style. This creates overall balance, which helps keep your hips looking slim and streamlined. Hudson Gwen Wide Leg in Oldmill, $165

Plus-sized: If you’re plus-sized, a darker-rinse denim is the way to go—just make sure it’s either straight-legged (slightly form-fitting) or a trouser style. Both of these looks are slimming. Torrid Denim Yacht Trouser, $52

Tall: When you’re tall, you can definitely rock long and lean straight-legged styles—or go retro and try flared, ’70s-inspired denim.

Boy figure: If your body is more straight up and down, opt for a mid-rise jean with a slight boot-cut opening or flare to create a curvier silhouette from top to bottom.
7 For All Mankind Skinny Bootcut in Malibu Sands, $189

Petite: Petite girls should stick with a slim-cut pair of jeans. Try a cute boot-cut or sexy, cropped skinnies.


“I have often said that I wish I had invented blue jeans: the most spectacular, the most practical, the most relaxed and nonchalant. They have expression, modesty, sex appeal, and simplicity – all I hope for in my clothes.”
Yves Saint-Laurent



White t-shirt

The “white t-shirt & jeans” is always a homerun. Slam dunk. Timeless and effortless look.  You can’t go wrong (unless you rip holes in your t-shirt or wear it entirely too large). Cotton, fitted, slightly wrinkled, whatever works for you. Add your leather belt & call it a day.  White t-shirt & jeans is a total blank canvas. I personally love to add a little over the top gold and bling or go casual and add a chunky statement necklace. Have fun with this look!

“It really is simple. Add an attractive tailored jacket –proof that you don’t need a new wardrobe to look polished & sophisticated” Tim Gunn


White button down

Gap & old navy are great places to pick up a white button down. Banana Republic and J.Crew can give you a little more professional or crisp option too. A man’s white button down is even more chic.

“Any time a cool girl or designer throws a man’s shirt into the mix we are reminded of the power that comes with that crisp simplicity”. Nina Garcia


Ballet flats, Boots & Booties

Each could hold its own e-course series!

Ballet flats have been adored by the fashion world & are truly chic and timeless. You can’t go wrong with a pair of black ballet flats, Chanel (black toe cap) are the quintessential pair, however Gap, JCrew and Tory Burch carry fabulous options too.

Boots have completely taken over the world. Thank goodness. Riding boots worn with dresses, skirts, jeans & leggings. Cowboy boots ( preferably Lucchese or Tony Lama if you’re a cowgirl purist-amen) are as acceptable with cocktail dresses ( hello Texas or SEC gameday) as they are with aforementioned white t-shirt & jeans ( I’m more of a “don’t tuck your jeans in your cowboy boots kind of girl…but what do I know?)  And always super cute with a fun flowy summer dress. Be prepared to spend a little money on your boots. I’m all about the leather looking aged and like a perfectly worn in saddle. No shiny leather please. Frye, the harness boot. Welcome to the club.



Brazilian made, classic flip-flop that feels like butter.



Fun fact: in 1918 Chuck Taylor, high school basketball stud, began wearing them & later promoted them and lent his name to the sneaker.

Converse is to the east coast cool kids as Vans are for the west. Or you can be a fashion rebel and do your own thing. Can I get an amen?



A dressy pair & a casual pair will be a great way to start when looking for your summer sandals. Fun metallic thong, ever classic Jack Rogers or a little gladiator will give you variety.


Rayban aviators & wayfarers

I love a pair of inexpensive trendy sunglasses as much as the next girl but nothing says effortless, timeless style like a pair of aviators or wayfarers. The end.


Shorts :

Ok. I’m treading lightly on the subject of shorts.

Good gracious. I’m not sure what has more of us feeling intimidated, bathing suits or shorts? Ya’ll. I have friends who are in their 30’s, gorgeous slender friends, who have thrown in the towel and declared themselves as “non-shorts wearers”. Ya’ll. Rise up and claim your shorts!  Most of us spend a considerable amount of time watching what we eat & exercising. We. Can. Wear. Shorts. Hallelujah.

Having said that let me offer you a few guidelines. (As per Real Simple Magazine)


If You Have a Tummy

What to look for: A generous fit through the middle to keep you comfortable and a wide waistband to help hold you in. Contrary to popular belief, “subtle pleats help, too, since they focus the eye lower, away from the stomach,” says New York City–based stylist Amanda Sanders.

What to avoid: Belts and patch pockets, which only magnify this trouble area.

What to pair them with: A flowy Empire-waist top. “It highlights the smallest part of the body—right below the bust—while concealing the midsection,” says Summer Robbins, a wardrobe consultant in New York City.


For a Tummy: Medium

Look for a roomy cut through the waist. Want to show off trim legs? Tapered cuffs will play them up.


If You Have Wide Hips

What to look for: A body-skimming (not tight) cut that creates a straight (not tapered) line from the widest part of the hips down to the hems, says Sanders. Dark fabrics with stretch are the most forgiving.

What to avoid: Pockets that line up with the side seams. These tend to pop open and emphasize the hips.

What to pair them with: Go with an eye-catching embellished blouse or a statement-making necklace to bring all eyes to your top half.


For Wide Hips: Long

Keep the shorts—and your look—sleek with simple details and a dark shade


If You Have an Hourglass Figure

What to look for: Contoured waistbands and high-rise styles will help eliminate the gaping at the midsection that often results with this body type.

What to avoid: Pairs that are cut straight up and down won’t do your body any favors.

What to pair them with: “A tucked-in shirt is a must to show off the waist,” says Michelle Smith, designer of the ready-to-wear clothing line Milly. She specifically recommends a fitted tank or a button-down with a skinny belt.

Look for a contoured cut that ensures a snug fit through the waist and hips.

Emphasize the smallest part of your figure with a bow-tied style that sits high on the waist.

A wide-tab waistband will hug your middle perfectly.


If You Have a Straight Figure

What to look for: “Any details that add texture and dimension to a super-straight frame, from defined pockets and pleats to prints and embroidery,” says Smith.

What to avoid: Plain and baggy styles make a boyish frame look dumpy and shapeless.

What to pair them with: Slip on a ruffled cami or a bejeweled tunic to give a boost to the chest, and use a belt to carve out a waist.

A gathered waistband and a voluminous shape will add extra swish to the hip area.


A high-waisted design, especially one in a bright pattern, will make you look curvier.


You may also check out the following for more tips on shorts per body type http://www.fitnessmagazine.com/beauty/guides/summer-beauty/the-perfect-shorts-for-your-body-type/?page=2


Little Black Dress:

You may find a total score at Target or H&M but the LBD can also be a piece in which you wish to invest. This piece will be a key player in your wardrobe for decades.  Classic. Effortless. Timeless.  Consider a little white dress too. “The LWD is the unsung hero of the dress department”.  Nina Garcia

“One is never over-dressed or underdressed with a Little Black Dress.”
Karl Lagerfeld