Film and TV Analysis

Elizabeth Keckley : From enslaved to dressmaker of the First Lady of United States

Welcome. This is the first post of the Black Fashion History Serie. We will highlight contribution of black creatives to Fashion Industry in the past and present. Starting off, is Elizabeth Keckley, credited as the primary dressmaker and friend of (the very first) First Lady of the United States, Madam Mary Lincoln.

(Author’s note : On second slide, last name should read Keckley and not Kelsey.)

Major thanks to the following publications for documenting the work and life of Madam Elizabeth Keckley.

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Four Valuable Fashion Lessons “Legally Blonde” Has Taught Me

Twenty years ago, Reese Wetherspoon brought the character of Elle Woods in Legally Blonde to life.

Recently, a cold rainy fall afternoon turned into an opportunity to re-watch the 2001’s comedy Legally Blonde. Here I thought, I would get a couple of good laughs and call it a day. Much to my surprise, I couldn’t help but notice how much I liked the professional outfits our heroine was sporting. Twenty years after the film’s release, most of the Elle Wood’s costumes remain wearable. Granted, I wouldn’t be borrowing her full fushia leather ensemble any time soon. But given how easy it is to fall in pattern of grey and black garments, my workwear could use a little touch of youthfulness and fun. (Let’s pretend we’re not in a pandemic and just living in Loungewear). As a matter of fact, from a fashion standpoint, Legally Blonde is the perfect backdrop for inspiration on young professional dressing.

Here are the four tips I learned from Legally Blonde :

Tip # 1 – Having a signature color creates continuity in your outfits.

Elle Woods holding her dog and nodding her head.Caption says "whoever said orange wwas the new pink was seriously disturbed"

Legally Blonde features a strong reference to pink. Twenty years later, if you wear an all pink look, chances are at least one person will reference Reese witherspoon’s character. Now you’re probably thinking : this is just a movie and I have no intention to wear an all pink look anytime soon. But here is my point. We can go on forever on all the benefits of a signature style: it saves you time, money and sets a specific image to the rest of the World. But settling down on what constitutes your own style, can take years and requires lots of experimenting. Which as you probably realize cost money.

So, how about narrowing down to a color ? You could start small by adding accents of your favorite color in the accessories (perhaps a bag, a necklace, or a belt). Going further, you could incorporate one piece of clothing in your signature color for every single of one of your looks.

Don’t believe me ? Look at the use of orange in fashion blogger Steffy’s outfits.

instagram feed of blogger steffy with multiple outfits featuring signature color orange
Elle Woods in playboy outfit
caption  says :  Oh, I like your outfit


Let’s start with a cheesy quote : “Confidence have no competition”. In this scene, Elle is invited to her first Harvard party which she had been told was a costume party. She shows up dressed as a Playboy Bunny only to realize that she is the only one in costume.

Instead of runing away defeated, Elle doesn’t let it get to her. She carries herself with a healthy dose of confidence and inhabits the same comfort as if she was simply wearing a good pair of jeans. Eventually, she almost convinces us that a bunny costume can be a regular outfit to wear to your student library.

I said almost.

Elle woods in playboy outfit, holding apple laptop package

Tip #3 : Shop in the men’s section

The First Day of School Ensemble

Shopping in the menswear section can be a great idea. First off, you will save money. According to CNBC, Woman clothings cost in average 6% more than men. This is in part due to the “pink tax”, a term used to define the practice of charging woman more than men for the similar services and products (data from Canadian Labour Institute). Given that male consumer tend to prioritize practicality over trendy pieces, you are more likely to find higher quality items at a lower price if you just go through the men’s section. Menswear brands will also favor classic silhouettes.

black model wearing menswear 
orange long coat and checkered suit pants.
@ PhabStudio

Trend Report :

The oversized trend is ever so popular. One way to acheive the look ?

Picking a regular men’s vest which should naturally fit looser on your frame.

The trick is to balance out the proportions. If you go with an oversize on top, compliment it with a slimmer bottom piece (ex : trouser).

Internship Fashions
Elle walking head up wearing polka dot  blouse with a figure hugging midi black sweather.
In the photo below, Elle balances out her necktie and blouse with a figure hugging midi black sweather.

Lastly, dressing in both men’s and woman’s section doubles the chance to find great items. Why limit yourself ?

Elle wood GIF. Caption says I completely agree

Tip # 4 : Don’t just wear the rack. Inject your personality into each outfits

The Courtroom Standout scene. Elle Wood wearing a pink dress with scarf at waist.

As you enter the professional world, you don’t have to mute your personnality and fall for the same grey and black garments. You can infuse your individuality in the details and wear colors. Granted, some of us have strict dress codes since the policing of woman’s body continue to exist in 2020, but you can still leave trails of your individuality through accessories such as jewellery and scarves.

Same picture of black model wearing menswear orange long coat and checkered suit pants.
@ PhabStudio

The Fashion Verdict

For me, the fashion lesson I take away from Legally Blonde is that being stylish in the workplace is a matter of utilizing the tools you have. Revisit the traditionally masculine garments ( necktie, blouse, cardigan ) and play with accessories to inject your individuality into your 9-5 outfits. Don’t be afraid to experiment as you develop your own signature look. As a matter of fact, it’s through trial and error that Elle shaped her impeccable professional dressing.

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Four types of messages hidden behind issa’s shirts in Insecure

Who knew a 100% cotton tee could carry so much weight?

If you’ve watched Insecure, then you noticed that through the various ups, downs, and characters’ growth, one thing that remained consistent is Issa’s love for graphic tees. The garments with bold messaging appear at least once in every single episode. Believe me, this is not a mistake. It is a deliberate move by Insecure’s Costume Designer Ayanna Kimani to insert “Easter eggs”, as she refers to them, into the show. In a 25 minutes episode format, the tees serve as valuable insights into the character’s hobbies, interests, and political views without having to address them in the script.

Let us dive into the 4 types of messages behind Issa’s iconic graphic tee collection:

(Disclaimer : For this discussion, I will also include sweatshirts.)

 I love to see if the viewers catch my little Easter eggs. I love to see how they interpret the wardrobe. I like to see that they’re understanding it, and then everyone showing love to the show, that’s the coolest thing.”

AyannA kimani for


Off Duty, Issa continues to sport her iconic collection of tees which serve as a declaration of love for black culture.

Issa wearing Mary J Blige concert tee in season 3 
black culture easter egg
Images via HBO

In the comfort of her own home, we see Issa lounging in her Miseducation of Lauryn Hill shirt, Mary Blige and Prince concert tees. This is as a nice homage to music icons and in the process, we discover that Issa’s musical taste are unapologetically black. We can almost picture her “borrowing” the Prince tee from her parent’s closet or stumbling onto it in a vintage shop.

Issa wearing The Last Poest sweatshirt with orange flare pants at her friend gallery. Pensive look on her face
 (Credit: Lisa Rose/HBO)

At her friend’s art opening, she swaps her classic cotton tees – jeans combo for an elevated version of the casual look. We see her in a black The Last Poets sweatshirt paired with flared pants. For those who don’t know, founded in the late 60s, The Last Poets is a group of poets and musicians rooted in black nationalism and the civil rights movement. They are credited  as the forefathers of hip hop and have been featured in songs by the likes of Biggie and Common. This is proof that Issa’s knowledge in music history runs deep and, as a result, couldn’t feel more authentic.

Interestingly enough, their costume designers have mastered the dual use of graphic tees. A noteworthy look is the Nina Simone “Feeling Good” shirt which not only praises the legendary singer but depicts Issa’s feeling as she undergoes a big transition in her life. With newfound clarity in both her personal and professional life, she is feeling good… great even.

“Most of the time when Issa is chilling, you’ll see her in a hip-hop T-shirt. I did that in Season 2 a lot, and I would always put her in a T-shirt that interpreted her mood.

Ayanna Kimani in Observer
ISsa wearing Different word shirt in her apartment
Different World Tee | Image via HBO

Additionally, the show pays homage to the films and TV shows like Waiting to Exhale and Different World who have paved the way for a show like Insecure to exist today.  The nineties were an era where black sitcoms were produced in mass, and Different World laid the groundwork for next generation of sitcoms. Not only did the show portray multidimensional black characters, tackled politics but each character had their own distinctive style. Much like Insecure. Likewise Waiting to Exhale is a reference film in the black community. In today’s climate where living black is an act of resistance, where the pain of women of color is exploited for the big screen (cue the struggling single mother trope). Alas, seeing Issa, a multi-dimensional black woman living a regular life, embracing her favorite artists and shows is nothing short of refreshing. 

2. An opportunity to show love to her city

Issa at lunch table wearing SuperMall green hoodie with graphic in orange and yellow.
Images via HBO

What New York is to Carrie Brenshaw (Sex in the City), Los Angeles is to Issa.

L.A. culture is an integral part of the show. When it is not mentioned through the script, be prepared to see it injected in one of Issa’s outfits. In season 2, we see Issa at her favorite taco truck wearing a denim baseball vest with the word Inglewood printed in red. Inglewood is a City of Los Angeles County where Issa lives. A few episodes later, we see Issa wearing a purple Outkast shirt paired with yellow sweats. This ensemble pays homage to the East Coast 90s hip hop duo while the color pairing is a nod to the Los Angeles Lakers. Perhaps the most memorable “Easter eggs” are the Nipsey and Prince Tribute. With the passing of Nipsey coinciding with the filming of season 4, the show decided to incorporate his Marathon Clothing line into Issa’s wardrobe. My favorite is the SuperMall Green Hoodie with its retro aesthetic very much in tune with Issa’s love of vintage.

Issa running outside her The Dunes apartment . She is wearing purple outkast shirt with yellow baggy sweatpants
Images via HBO

3. Use as a political vehicle

Dubbed “conscious clothing”  by the  Costume Designer Ayanna Kimani .

T-shirts are also used to vehicle a political statement. Here, Hump shirt is making light of Donal Trump’s infamous slogan ” Make America Great Again”. Later, the show also revisits D.a.r.e, a failed anti-gang and drug program. One could interpret this as an invitation to push Issa outside her comfort zone. The most daring shirt is perhaps America’s Horror Story t-shirt by Inopportune Portrait, which features tiny Donald Trump figures. Interestingly, Issa wears it as she wakes up from a bad dream, anxiety-ridden after being ghosted by Nathan. Shot in 2016, perhaps this is a social commentary on America’s own political nightmare? One who, unlike Issa’s, they can’t seem to wake up from. Who knew a 100% cotton tee could carry so much weight?

Issa lying in bed wearing HUMP Make America Gyrate Again
Images via HBO

4. Tees are also a sign of oppression

But her tees can also be a symbol of feeling stuck. The “We got y’all ” t-shirt with its controversial image of a white hand holding three black children isn’t a symbol of comfort. It represents Issa’s workplace, where she feels stuck and not understood by her colleagues. The same place where after a fallout with Frieda, her only work friend, she wears a Public Enemy shirt, a direct representation of how she feels her colleague perceives her.

Zoom on Issa sweatshirt FBI killed Fred Hampton in public transportation
Images via HBO

As a matter of fact, t-shirts are used to illustrate tough messages such as the historical tensions between the FBI and black community through the “ FBI killed Fred Hampton” garment. While the sweatshirt worn by Issa on regular day to work is never mentioned in the storyline, the message is enough to raise a discussion between viewers. Not to mention the Trayvon hoodie worn by Molly on a girl’s night in as a tribute to the young victim of police brutality. What strikes me is the juxtaposition of heavy political messages with the normalcy of the characters who continues on their lives. Here fashion is used to show hard realities through the subtleties of clothes. It illustrates how black people navigate their days between microaggressions and traumatic experiences. Insecure doesn’t shove these hard messages down your throat, it has its characters wear them proudly on their chest and pushes you to reflect and investigate. And to you, I ask: what can be more authentic than a powerful message worn literally on one’s chest? That, my friend is how powerful fashion can be.

 More read on the subject :

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A look at Issa’s Fashion Evolution through her “Glow-up” Journey in Insecure

As the recent season is wrapping up, let us look at  Issa Dee’s style  evolution .

After ten compelling episodes, your Sunday rendez-vous with Insecure are ending. For the last two months, you followed Issa and her friend Molly as they with no shortage of laughs and relatable awkwardness navigated the currents of relationship, new jobs, and friendships. In Season 4, we see our characters slowly break away from their pattern of questionable choices and  get to witness serious growth. And along with that? Some killer fashion moments.  The plot, the dialogue with all its twists has already been diligently dissected by its loyal following but what about its fashion moments curated by costume designers Ayanna James- Kimani and Shiona Turini? They say that an image never lies. So if Issa is in the process of “glowing up”, how did it translate to her style?

“I think [my job is to help] relate the character’s story, to make it feel personal, so when the audience is watching they feel like, Oh, I know that person. That was the key in the choices I made for all of the characters. Issa’s world is a lot more color and texture, playing with prints and patterns.     – Ayanna Kimari, Former Insecure Costume Designer in People

Issa’s Personal style: quirky with lots of prints

A quick glance at Issa Dee’s looks through the seasons and you’ll spot what makes up her favorite pieces: bold prints, cut out pieces, and provocative graphic tees. If anything,  Issa has never been shy with fashion and has worn every pattern imaginable from west africain prints to classic plaids. It’s her ability to pair different prints and colours in one outfit that makes her looks so undeniably Issa. At first, you might reject the unsuspected pairings, but in a matter of time, the looks grow on you. You can’t tell if it was a happy accident, a result of grabbing the first clean clothes she could find or simply an innovative fashion moment. It feels quirky and true to  Issa, the same person who free-style raps in front of the mirror to build her confidence or release her fears and frustrations.

Credit :

Likewise, cut outs and fringes on a jacket or shirt are another way Issa injects her fun personality on what could have been an otherwise boring outfit. The Crepe Silk Fulani Blouse by black-owned brand Maki Oh is an example of that. The large cutout in the middle of the shirt shows off her toned abs and presents a fresh take on the crop top trend.

As the title suggests, the show is about Insecure Issa and through her appearance , that means that there is often a disconnection in her looks

Disconnection in her looks

Ultimately, as the title suggests, the show is about Insecure Issa, and through her appearance, that means that there is often a disconnection in her looks. Here the overlapping fabric can’t help but bring unwanted attention to her lower abdomen and ruins the overall look. As costume designer Ayanna James explains in an interview with Racked, Issa wardrobe consist of thrift and vintage pieces  as her “world is supposed to feel more lived-in, a lot of her stuff should’ve felt old.” Which makes sense considering her nonprofit salary. While thrifting is a great way to collect unique pieces, a fatal mistake one can make is failing to pick clothes that fit your body.

Credit: Justina Mintz/HBO Season 2 (For Promotional Use)

The acid wash khaki print dress with the bright silver straps in season 1 is unflattering to her figure and wash down her skin tone. Coincidently, Issa wears it while she desperately attempts with little success to mend her relationship with Lawrence. Her outfits ultimately reflect the state she is in: lost and in search of direction. Both in her professional and love life.

Merie W. Wallace/HBO

Utimately, Issa is glowing-up

Credit: HBO/ Costume Designer: Shiona Turini
Sidenote: Look at the contrast between (LEFT) the outfits worn by our career woman Condola and Molly and (RIGHT) Issa who is aspiring to level-up in her professional life and establish herself as a successful event planner. Issa’s NANUSHKA outfit is prime casual chic – the shape is classic but the acid wash in copper brings a fresh pop of colour and compliment her brown skin.
On the opposite, Condola and Molly are wearing timeless structured in cool colors.

But in season 4 Lowkey distant, the acid wash prints get a redemption in a fitted midi dress worn by Issa during a business meeting. The NANUSHKA number sums up a shift in Issa’s sartorial choices.  Now, our beloved heroine has gained a sense of purpose in her life; she focuses on herself and sets on planning the best Block Party and parallels to that, her outfits now appear polished. Her professional network is rapidly expanding, and she is trying her best to refine her image along with it. Her fashion style remains authentic, but prints are more subdued and cohesive with the overall looks while she favors geometric cutouts that are sexy and flattering to her figure. She even explores different hairstyles and includes accessories that add depth to her outfits. In season 4’s Lowkey Happy, Issa grace the screen in a  rich red Thebe Magugu Safari Jacket beautifully cinched in at the waist with cut-outs exposing the neck and shoulders. Having recently joined the dating pool, it is fun to see our heroine experimenting with her sexy side. The tailored piece is in direction with Issa’s new image: polished yet sexy and feminine.

Photograph by Merie W. Wallace/HBO
Photograph by Merie W. Wallace/HBO

As Costume designer Shiona Turini explains in  The Cut  We stuck to an aesthetic that feels authentic to her character, but elevated it. This season, as a reflection of her professional goal, she purchases — and then returns to Opening Ceremony — clothing that she thinks fits her ideal self. She’s not yet where she wants to be, but she’s making more conscious choices into the woman she’s becoming.”.

As viewers, we’ve all had similar episodes in our life where we’ve upgraded our style in anticipation of our ascension up the professional ladder. For Issa, this means that her style is finally growing out of its college-phase and moving towards a classier and more feminine look.

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What are your thoughts? Do you have any suggestions for another character style analysis?

Want more ?

Tune in the next week for Part 2: How graphic tees are used as political and social tool in Insecure.