Dressing The Part For Every Situation
By Amanda Shipley
Situational dressing. It’s become my calling card. It’s what I do. It’s what I love. And it’s what inspires others or so I’m told. It’s only a footnote to my fulltime career as a lawyer, but more on that later.
I’ve always cared about clothes. My mom can tell endless stories about taking me shopping to Macy’s as a tween and how I would request that the tags be cut off there in the shop so I could wear my new very coordinated Esprit outfit home. Who would see it? My mom. Maybe my sister, brother or dad if I was lucky, but it didn’t matter. I just loved clothes. I loved feeling put-together. And I loved feeling on trend – even when it was the 80s and very much not a trend with staying power.
That didn’t abate with age. In high school, I would read Vogue cover to cover. I knew all of the supermodels. I knew all of the photographers of the supermodels, I knew all of the make-up artists of the supermodels, and I knew the designers of the supermodels – all very useful things for a fifteen year old living in the suburbs of Atlanta, to know. In college, I learned from my way-more-stylish sorority sisters from California about $100 Diesel jeans and, finally, on my semester abroad in Florence, during the days of the lira, I could afford the name brands. With Prada and Gucci one-third of the price as at Saks, I could buy the masterpieces I’d always coveted.
So for years, I read and I researched and I bought and I wore, but my look was sort-of directionless. And that was ok because I was a lawyer and, more importantly, I lived in Boston which is (a) very very cold and (b) very very boring with respect to fashion. I think Boston ranks second behind Washington, DC for the highest percentage of women wearing button-down shirts.*
But then I moved to London at the end of 2010. In London, as long as you didn’t work in The City (ranked third behind Washington, DC and Boston for the highest percentage of women wearing button-down shirts)*, you can get away with a lot. In London, you can almost wear tights as trousers to work and get away with it. In London, I started to find my way.
It was in London when I first heard about situational dressing whilst watching #RichKids of Beverly Hills on E! back in 2014 (don’t judge). Around the same time, I was hitting my stride with respect to what I pictured myself to be as a partner in my own law firm. It was then that I started pushing the boundaries of what it looked like to be a lawyer and, for that, situational dressing was the perfect fit.
What ‘situational dressing’ means in practice is to dress up for the occasion of the event. Dress for the role. Dress for the situation. So, for example, you’re going to Hawaii. Don’t pack dresses that would be just as fitting for a trip to Italy. No! You pack your palm tree prints. You pack your tropical prints. And you pack your pineapples. That, my friends, is appropriate for the situation.
Inspired by the #RichKids (has anyone else ever typed that sentence?), I began implementing situational dressing as a policy in 2015. I agonized over the perfect outfit to mount Machu Picchu (athletic wear but something that would photograph well for the view of a lifetime). I channeled my inner ‘power woman lawyer’ look to speak at a conference (vibrant bold blue Lanvin dress and Gianvito Rossi shoes that could only be worn safely within a conference room at the hotel where I was staying). And I wore almost exclusively Osklen and Adriana Degreas during a trip to Brazil since the designs of the fabrics were reflections of the Rio landscape. Citizens of Humanity overalls for my boyfriend’s farm. Superfine Rebel skinny jeans for a Harley ride. All, in my opinion, perfect for the situations.
And, really, once you embrace situational dressing fully, it’s hard to dress any other way. Almost every day (except non-client-facing days when yoga pants and sports bras reign), I channel the look I am going for. Meeting with my conservative bank client? Something more traditional (neutral nail polish, Aquazzura Belgravia pumps, and Stella McCartney pantsuit). Meeting with my potential client in the music industry? Something that says, “I’m not your typical square lawyer, but you can still count on me” (Valentino Rockstud shoes in black patent – best investment ever; Whistles button down – acceptable if in a print rather than solid colour; and Rag & Bone cigarette trousers). Meeting my girlfriends for tea? Something pretty (anything Dries Van Noten). And don’t even get me started on the work that goes into a holiday!
But situational dressing becomes a way of life and it can make every day a fashion adventure. You can play a part that will affect your day and outlook. It’s something you can embrace fulltime (like me) or part-time (like many of my friends and colleagues). To do so, I wanted to leave you with three tips:
- Start with a vision. This can be something already in your imagination from a dream, film, or advert. It can be something that you actively seek out on Pinterest based on where you are going. Or it can simply be the news and witnessing the Prime Minister stepping off the plane in America with the most ‘female boss’ winter coat you’ve laid eyes on. This will be the look I pursue the next time I need to look particularly ‘female boss’.
- Don’t be afraid if you’re the only one who showed up dressed for the party. People are too casual these days. Very few people value the importance of an occasion. This is most troublesome in a grand venue like the Royal Opera House when people are wearing trainers. Personally, I think trainers should be banned from anything royal unless it’s some sort of run. But don’t let this discourage you! After hours of tireless research for my recent safari (no neon – animals spot it; no black – mosquitoes love it; yes neutrals – I don’t own any), I am pretty certain that, other than my good sport of a boyfriend, I am the only person who took the dress code seriously. But guess what? I didn’t care. I looked awesome. I felt awesome. And my pictures are awesome. If you embrace situational dressing, you must be prepared to go at it alone. But if you love situational dressing, you will know that you are the one dressed appropriately and appreciate the thrill of an occasion!
- Don’t overdo it and always do you. Situational dressing is supposed to be fun. It’s supposed to make you Thus, it’s important not to overdo it. There are some situations that would price me out of house and home (think – long fur coat in Aspen) so I have to find the look that I can afford that works for that location or event (grandmother’s fur shrug and borrowed Herve Leger bandage dress). Further, when purchasing items for your situation, I encourage you not to go fully with disposable one-off items. Maybe a fun palm tree print piece or two from H&M can supplement your wardrobe, but being able to adapt items to look appropriate in different situations is important too. For example, aforementioned Superfine skinnies also dress up with a stiletto and the Machu Picchu climbing outfit now sits center stage at yoga. The challenge is half the fun! You also want to do you. Situational dressing is not supposed to be a costume. You want to feel as great as you look and if you push too far outside of your comfort zone, you’ll feel as silly as you do wearing face paint. So if you’re not sure you’re ready to wear the flamingo blouse in Palm Springs, wear the flamingo-pink colored blouse instead. Or the flamingo-printed lingerie. Nobody will see it but you will know that you dressed for the situation and you can test how you feel without quickly hiding back in your occasion-less shell.
Overall, situational dressing makes me very happy and I’m not alone. Mariah Carey refers to it as “festive” all whilst swilling a glass of champagne on a dance floor. Situational, occasional, festive. Whatever you call it, it allows me to channel my creativity into something other than legal arguments and has a guaranteed rate of success.
*Rankings are the author’s own guesstimate.
Amanda Brill Shipley is a US Immigration attorney at TGL Shipley Parisi in London. Her alter ego, Brelle Woods, can be found on Instagram @brellewoods.