Smart, Sassy and Stylish:
Meet Miss Amy May

Smart, Sassy, & Stylish: Meet Miss Amy May

It has come to my attention that there’s a lot of negativity on the internet (shocker I know). Scrolling through my Instagram feed, I see a lot of comments about people combatting body shaming and unwelcome criticism, lack of self-confidence, and all around negative energy. And it’s not all that surprising, considering images are paraded in front of our eyes about the women we’re supposed to be, the body we’re supposed to have, the items we’re supposed to buy in order to achieve some unrealistic ideal. And when all of these images are clouding our vision, it’s hard to see through it to the amazing women who are the best form of inspiration – cause they’re just being their non-airbrushed, un-photoshopped, unapologetic, real-life selves.

I‘ve been thinking for quite awhile about adding a feature to The Dressed Aesthetic where I introduce you lovely readers to smart and stylish woman I find inspiring and put some welcome, positive messages across our retinas. I really love the idea of creating a celebratory support network, where we can be introduced to other similarly minded, positive women, and simultaneously bolster those inspirational women up so that can continue to be fabulous and inspire. Sharing in beautiful things, spreading positivity – in a way it keeps us all connected and reminds us that, you may be the only one in your workplace, circle of friends, or town proudly donning your petticoat or rocking those pincurls with aplomb, but you are most certainly not alone.

So, welcome to my first installment of Smart, Sassy and Stylish (and other alliterative things).

Smart, Sassy, & Stylish: Meet Miss Amy May
Dress: Collectif Clothing

Brace yourself ladies, it’s Girl Crush Time.

Meet: Amy, aka Miss Amy May. Passionate Pinup blogger. Femme Fatale. All Around Awesome (I told you I was really into alliteration today). I found Amy on Instagram, and quickly followed the trail of fashion breadcrumbs to her blog, Miss Amy May. I swooned. I laughed. And then I got one heck of a girl crush because this gal is inspiration personified.

You know when you ‘meet’ someone and they just sort of speak your language? You can cut through the small talk and move right on over to Mutual Appreciation? That was pretty much how I felt when Amy and I first started chatting. Her blog and Instagram feed is littered with gorgeous outfits and a “take no prisoners” attitude when it comes to sexism, body shaming, and conformity. She advocates glamour and self celebration, and there are no holds barred when it comes to product reviews and telling it like it is. As a pioneer of the #LovingMeIn2015 hastag, she’s the first to celebrate her curves and be up front about various “squidgy” bits and how she’s learned to love the body she has – this bombshell bathing suit post says it all.

Her candid, inspirational words ring true to all of us, and my day always takes on a bit of extra sparkle when I’ve found my way to her blog. So I thought she was the perfect icon to kick off Smart, Sassy, & Stylish. Thankfully, she agreed (or I would just be talking to myself here). I was able to get the nitty gritty on her sense of style, life as a pinup, body positivity and marrying the perception of the world with the reality of her fabulousness.

Q: Tell me a little about yourself. 

Amy: “I’m a former farm girl who works as a Warehouse Supervisor by day and dresses in the 50s style in her spare time. I’m one of five kids, aunt to six niblings, and once I bond with someone I’m theirs for life. I’m fond of dinosaurs, sparkly crystal jewellery, eyeliner flicks so sharp they could kill a man, and talking in funny voices. I’m from the UK, Sussex born and bred, yet most people ask me where my accent is from because, apparently, my penchant for said silly voices and my decade-plus of having American friends means I sound ‘unique’ and am regularly mistaken for being American, Australian, and even South African and Dutch??

I eat too much and am either a bit hyper or flat out chilled. I hate slow walking people in public and I get anxious driving to new places. My seams are almost never straight. My hair skills are only average. I have the usual 10 toes, but I do have a random white eyelash on each eye. I am stubborn, a bit of a contradiction, and finding my pinup style has helped me grow more confident in my own skin.”

Smart, Sassy, & Stylish: Meet Miss Amy May

Smart, Sassy, & Stylish: Meet Miss Amy May
Top: Stapless Bustier by Pinup Girl Clothing

Q: When did you start Miss Amy May and what was the main catalyst?

Amy: “I’ve always written in some form–I spent most of my teens and a few years in my early 20s writing fiction of one form or another, just as hobby. But honestly it wasn’t until I regularly began getting questions on Instagram from ladies wanting to know about beauty tricks and tips, info on sizing of what I was wearing, or how I even found my clothes, that it occurred to me I might be able to start a blog. I asked on IG if anyone would be interested in reading should I begin one, and I was floored by the enthusiastic response. Since then I’ve found it really fulfilling sharing my pinup life with everyone and trying to help and encourage not only my fellow pinups but those who are still only dreaming about the possibility of becoming one.”

Smart, Sassy, & Stylish: Meet Miss Amy May

Q: Can you tell us a little bit about your evolution into a Pinup? Have you always been so stylish?

Amy: “I would say, no, I’ve not always been so stylish. Due to weight struggles, I spent most of my teen years terrified of trousers and then my early 20s being terrified of dresses, flip flopping on which I thought made me look ‘too fat.’ I relied heavily on wearing jeans and empire waist tops with long necklaces back when the ‘boho’ look was in fashion. I didn’t look terrible, by any means, but I didn’t feel I had a distinctive style. Getting to grips with trying to find a healthy weight for me was part of my transformation as I moved further into my 20s, but really the big change came from my hair. Naturally curly, it got so supremely damaged from a one-off extreme heat styling session that I ended up with damaged hair I couldn’t style and, a life-long curl lover, felt like I had lost part of my identity. I began experimenting with wetset pincurls, as that wouldn’t require heat to help me recreate the curls I no longer naturally had, and from there my love for the style, dormant and secret beforehand, began to blossom and move to the forefront of my life and my style.”

Smart, Sassy, & Stylish: Meet Miss Amy May
Dress: Pinup Girl Clothing // Cardigan: similar

Q: Where should someone begin who is looking to start his or her own pinup journey?

Amy: “Wherever they feel most comfortable. For me it began with hair, then moved tentatively into clothes while I practised the makeup. But for someone else they might feel they want to start with the makeup, or only even adopt one facet of the style. It’s easy to say you ‘have’ to do this or that to be a pinup, but every person is different and this style has no rules; it’s an art form, in a way, long forgotten and overlooked, and if you want to test it out for yourself then all you really need is that will and a little bit of practice. Yes, the hair and makeup can be hard to master, if you go all out, so don’t get down on yourself if you don’t feel you look as polished as you would like to. We are all learning, constantly. You will too. Just let yourself be drawn to the things you like, indulge them, and, hopefully, watch your confidence in those things and yourself grow.”

Smart, Sassy, & Stylish: Meet Miss Amy May
Dress: Chi Chi Clothing (ohhhh wish listed) // Fur wrap: Similar here & here
Smart, Sassy, & Stylish: Meet Miss Amy May

Q: I love the dichotomy of your professional life and how you fashionably express yourself. Could you tell me a little about your job, and what a day typically looks like for you?

Amy: “I work for a logistics company in their pick and pack warehouse, and have been with the company many years. What I do day to day changes all the time, as my position deals with a stream of alternating clients and the particular tasks they outsource to us. Sometimes I can spend 3 days straight putting lipbalms through a machine so they receive a new barcode label and other times I do 7 different tasks in a day and the next thing on the to do list is in constant flux. Depending on the time of year, I have a varying-in-size pool of staff under me that I direct in their day’s activities and possibly direct to other departments that are overrun and need help. It’s not a glamorous job, but I like the variety of it and how active and dirty it can get, since that kind of work is not alien to me as a girl who spent the first 19 years of her life on a dairy farm. In the past week I’ve done things as varied as fulfilling 50-odd textile orders cutting fabrics, supervised some (always-soul-crushing) stock counts, loaded new stock onto our barcoding system that allows us to keep track of where any particular product is in our whole warehouse, organised a series of jobs labelling boxes of Christmas gift stock for dispatch to huge nationwide chains, and jumped in to help in a few of my old departments picking and dispatching orders when they were too inundated to handle it alone. It’s change all the time.”

Smart, Sassy, & Stylish: Meet Miss Amy May

Q: Do you find you have to fight against gendered stereotypes in your workplace?

Amy: “You might think so, working in a men-heavy industry, but not really. Occasionally you’ll get a delivery driver who thinks because you have a uterus it’s acceptable that he, as a stranger, and often well past his mid-life years, call me ‘babe,’ ‘darling,’ or ‘sweetheart.’ When I get that I reply shortly, coolly, and ignore their over familiarity. But our company is a small one, family run, and actually with half the staff as women these days. I’ve been there for years, since back when there were only a handful of us women and mostly men, but we all see the company as a team effort and all the men I work with see me as part of that team. Plus, I’m strong and hardly ever need any of the men to lift something for me, so that helps.”

Smart, Sassy, & Stylish: Meet Miss Amy May
Top: Stapless Bustier by Pinup Girl Clothing

Q: To borrow from one of my favorite interview questions I’ve ever been asked: We live in different worlds: work, friends and family. If you could describe each set in an outfit, what would it be?

Amy: “For work it would be the literal steel-toed boots, jeans, hoody and hi-vis jacket I have to wear. It’s about practicality and warmth. For friends, it would be a fabulous swing dress with bright colours, a huge gathered skirt and a pretty bustline–with them is when I most get to dress as my pinup self, and it’s also a time I look forward to every week because my friends are lifelong and I love them so much that I get excited to see them every time we meet up. Plus, I’m probably loudest and most boisterous with them, so my outfit would reflect that. With family, they are my yoga pants and t-shirt; they’re comfortable and relaxing and make me feel at ease. There’s a lot of us and we’re very close, and while I do dress up for family events the same as I do for anything else socially, it also doesn’t bother me at all to see them with my bare face and still in my pjs.”

Smart, Sassy, & Stylish: Meet Miss Amy May
Dress: Lydia Dress in Rose Border Print by Pinup Girl Clothing

Smart, Sassy, & Stylish: Meet Miss Amy May

Q: Staying true to yourself takes courage – and can garner both positive and negative comments. How do you manage public opinion?

Amy: “I’m very lucky that I can’t recall ever having a single negative word spoken about my style since becoming a pinup. Strangers stare, and of course there’s a possibility some of those might be wondering what the hell I’m wearing, but generally in public I get smiles or am stopped to be paid a compliment. The few people who have asked if I’m in ‘costume’ don’t mean it in a derogatory way, they’re just amazed and surprised, so I don’t take that as an insult. Occasionally I get the impression from some people that putting so much effort into my style is a negative thing, like how silly to be so overdressed for seeing my best friends, but if people can’t wrap their head around the idea of embracing life by doing any small thing that makes you happy and makes you look forward to going out, rather than feeling anxious as I used to years ago, then that says more about them than it does about me.”

Smart, Sassy, & Stylish: Meet Miss Amy May

If I didn’t have this blog…I wouldn’t have had a reason to climb onto wave breakers in heels and a swimsuit on a cold windy May day while strangers watched. I wouldn’t have wanted to share my truth about my body with other women in the hopes that they won’t feel so alone or scared of the truth about their bodies. I wouldn’t have seen this picture below and been like ‘DAAAAAMN, Amy, you fine as hell, girl.Miss Amy May

Smart, Sassy, & Stylish: Meet Miss Amy May
Bathing Suit: Unique Vintage

Q: I’m so intimidated by non-sewing DIYs, but you always make them look so effortless. I particularly love your footwear DIYS (those bedazzled shoes are on my list to try!) – where do you get your ideas? Any tips for first time DIYers?

Amy: “Normally my DIY ideas come from budget restraints. I might see a gorgeous pair of unusual shoes, fall madly in love, then realise they cost $300 and feel sad. So I just figure out how best I can recreate that style or something similar with the emphasis being on time put in and effort made to achieve the result, rather than what money I can pour into it. Not everything I’ve ever made is a recreation of something I’ve seen, but normally it has stemmed from me seeing something pretty–whether it’s a scrap of particularly pretty lace, some adorable ribbons, a stunning crystal brooch–and been inspired to let my creative juices flow. My only advice is to just get creative with your materials, remember to be practical about considering how your item will wear and potentially get worn down or damaged, and always make sure to wear protective clothing where needed. There is nothing sadder than ruining a good dress because you got too excited to remember to put on an apron. Old newspapers are your friend!”

Smart, Sassy, & Stylish: Meet Miss Amy May
Skirt and Top: Pinup Girl Clothing
See Miss Amy May’s tutorial for these Cinderella Shoes
Smart, Sassy, & Stylish: Meet Miss Amy May
See Miss Amy May’s tutorial for these Bedazzled Flats (seriously, I want to bedazzle everything)

Q:  If you were a superhero, what would your superpower be?

Amy: “Oh man. I think I’d need to be able to teleport/apparate. I have so many friends scattered around the country and the world that it would be lovely to be able to see them whenever I wanted rather than us having to forward think to match up our schedules, and I would love not to have to get trains/planes to see some of my favourite people.”

Smart, Sassy, & Stylish: Meet Miss Amy May

Q: Do you have any advice for women who haven’t quite grown into their confidence yet?

Amy: “I would say that if you look at someone and marvel at their confidence, know that while that probably isn’t fake it also probably isn’t a 24/7 thing either. Everyone has moments of doubt or insecurity, and all of us have parts of our minds, personalities and bodies that we worry over. You aren’t failing in any way if you are struggling to feel confident. But because you deserve to be happy, try to do things that do make you feel good. Try the new hair style. Buy the puffy skirt. Go to the class you’ve always wanted to take. Arrange a special night out with friends. Take up the hobby you’ve always wondered about. Keep applying the red lipstick in the comfort of your own home until it stops looking ‘weird’ on you. If you keep testing yourself in small ways by inviting newness and happiness into your life then confidence will begin to blossom in you. Thrive on it and keep building on it as it comes. I still have a long way to go myself in being confident across the board, but since embracing the pinup style I have become massively more confident than I was before.”

Smart, Sassy, & Stylish: Meet Miss Amy May
Dress: Collectif Clothing

Q: To end, finish this sentence: When I grow up, I want to be…..

Amy: “Happy. Even since I was a kid, it’s all I’ve ever wanted. And it’s not that I’ve ever been unhappy really. I had some anxiety issues in my late teens and early twenties, and suffered some close familial loses during those times too, but even then I still didn’t feel unhappy deeply as a person. They were just life trials to get through and I remained grateful for what I did have during those harder periods. I think because I’ve always been fairly laid back at my core, slow to do things, not sure what ‘big’ things I want or need in life, the thing I’ve most loved and most wanted to continue is being able to say, overall, that I am content and happy. If I can grow old, look back and say I spent most of my life a happy person, no matter what I did, then I will have no regrets.”

Smart, Sassy, & Stylish: Meet Miss Amy MaySmart, Sassy, & Stylish: Meet Miss Amy May

Back when I first discovered Miss Amy May and was bumbling through as an Instagram neophyte, I remember a post where she gracefully accepted a compliment she had received, but also cautioned women not to aspire to be anything other than themselves. Not to succumb to envy or start a sentence with “I wish I had your…” Not to wish you had her body or wish you had her style. To not emulate her sassy acerbic wit or her luscious locks, but rather find the parts of you that need celebrating. That need no apology.

Seriously, THIS is the woman I want gracing my magazine covers and the woman who’s voice needs to be heard by impressionable young women everywhere. This is the kind of gal I want to laugh with, to grab a burger with, to turn to when my confidence hits an all time low only to charge forth into the next day with renewed energy. And, thanks to the wonders of the internet, with a few quick keystrokes we can infuse ourselves with a bit of Amy-fied inspiration, and then look around with new eyes and realize that awesome is everywhere – we just have to know where to look.

I had the best time getting to know Amy a bit better and know the retail sector both fears and lives for the day when she and I are in the same time zone. As she so perfectly said, “One day we will shop together and it will be like the universe has imploded in a shower of handbags and shoes and burnt credit cards.” Beautifully put.

For inspiration and general day to day badassery, I highly recommend following Miss Amy May on Facebook, Instagram, Twitter and her blog. Head over, give her a read, give her a follow, give her your endless blog-devotion (you won’t be sorry).

Go forth and be fabulous!



Outfit Details:
Supplied where possible. For the rest, check out Miss Amy May’s fabulous blog!

All photos in this post courtesy of Miss Amy May


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The Dressed Aesthetic

8 comments on Smart, Sassy and Stylish:
Meet Miss Amy May

  • Fran

    I too came across Miss Amy May on Instagram, and always enjoy how she brightens up my feed. So interesting to get to know her a little bit better, what a doll! I’m really looking forward to more posts on your new blog segment, so great to have some body positive role models out there. xox

    • (author)

      Isn’t she just amazing? I loved finding out a bit more about the other sides to her – fascinating, amazing woman all around! It’s so awesome to know you loved the fetter – I’m already planning for the next few wonderful ladies to interview in the coming months – stay tuned! 🙂 xx

  • SaraLily

    I LOVE this! I can’t wait to see more powerful women featured here too! I love Amy as well as follow her religiously. Such an awesome laid back gal with bombshell abilities! She’s the perfect choice to introduce your new feature! 😉

    • (author)

      Thank you sweets! I’m really excited about this feature – I totally agree Amy was the best Ambassador of the movement. 🙂 I’m all for finding modern heroes and women who are the best versions of themselves and encourage other women to do the same! xxx

  • CiCi Marie

    Great interview and I’ve loved finding out more about Amy, although was already avidly following her on Instagram and her blog, of course. I completely agree with all of your thoughts on what makes her so especially fabulous – and I really wish all women could take such a positive stance towards other women at all times. She is an inspiration and a great way to kick off a great interview series! CC x

    • (author)

      Thank you – Amy was so much fun to interview! I find the only way to fight negativity is with positivity. And you are SO right – why women like to tear each other down is beyond me. We’re so much better when we life each other up and push each other to reach our full potential. I’m so glad you were already following Amy. Whenever I really need to karate chop a particular day, I go to some of my favorite posts of hers. The amazing bathing suit post she did recently is at the top of the list! 🙂 xx

  • Lauren-Blair

    Awesome post! I think I’ve come across her once or twice, but I’ll have to follow her more religiously because she seems awesome! I have a guest blogger section for mostly the same reasons that you stated, so awesome! And, if you ever want to collab on each other’s blog I’d be totally down because you’re on my list of people to ask (I’ve been slacking off BIG time this 2015 year lol). XO

    • (author)

      Thank you sweets! And trust me, you will LOVE her blog. Full of all kinds of inspiration and a reminder to just keeping doing ‘you’. And I would love to work together sometime on a post! I think it would be really fun. How is the blog rebranding going?? I’m very excited to see how that turns out and what name you’ve chosen. 😉

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