Mary Houlihan is the stylish, brogue-wearing founder of Tailored Tomboy, a new online service catering to tomboys who need serious advise on tomboy styling. The passionate stylist is hoping that her affordable services will help tomboys in America and beyond find their unique individual styles easily, and simply. We spoke to this effervescent-spirited entrepreneur about Tailored Tomboy and the vision behind her company.

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Tailored Tomboy Kicks Up the Dust In True Tomboy Style Fashion Tomboy Tarts

   MARY HOULIHAN IS THE FOUNDER/STYLIST BEHIND TOMBOY STYLE CONSULTANTS, TAILORED TOMBOY

Style-wise, being a tomboy can be frustrating as we borrow pieces willy nilly from the men’s and women’s lines and try to make these hybrid looks work. Now, you can puking your guts or pounding your fists into the air in front of your closet because the tomboy world now has an official stylist and advisor who can help you navigate the oft-confusing and blurry world of tomboy style.

Your gender-bending muddled Mrs Doubtfire or Tootsie days are over because now you can gender bend as much as you want thanks to Mary Houlihan, founder and owner of tomboy styling advise company, Tailored Tomboy, based out of Chicago.

Tailored Tomboy is for ladies who don’t feel understood in the clothing retail market. It’s for ladies like us who enjoy borrowing styles frequently from men and blending them with practical female functional pieces.

It’s for tomboys like us who like to ride bikes, travel extensively, sing karaoke and are able to discuss politics and do nerd-geek all in style.

Mary has been styling for over 5 years and most recently, she worked for Trunk Club. She says the “best part of my job is helping women feel comfortable and confident in their clothes.”

Mary will help you disentangle your style from what is hip in fashion today. She will also help you dress to impress your inner spirit, and motivate you to be unapologetically yourself! Hell yeah!

Tailored Tomboy Kicks Up the Dust In True Tomboy Style Fashion Tomboy Tarts

   TAILORED TOMBOY WILL GIVE YOU AN OBJECTIVE PERSPECTIVE ON TOMBOY STYLES THAT WILL WORK BEST ON YOU

Mary’s process is as simple as a BLT . She’ll have coffee with you in person or an hour-long online session to find out what rocks your tomboy socks and from there she’ll tailor her services to best fit your wardrobe needs. Consultations are always free and if she can’t help you, don’t fret. She’ll still give you her best suggestions for achieving simple tomboy style.

Step 2. If you’re in the vicinity, Mary will take you shopping! (How cool is that?) Based on your consultation with her, Mary will come up with a one or two stores that best fulfil your needs. She will be honest with you and talk to you about where to splurge and where to save in your wardrobe. She promises to make it fun and painless as we all know, tomboys are not big fans of shopping and hanging out at malls for hours. We’d rather be skateboarding, sporting, travelling, sky-diving, watching our favourite comic book movie or reading a Kafka novel at the local coffee shop.

Tailored Tomboy Kicks Up the Dust In True Tomboy Style Fashion Tomboy Tarts

   TAILORED TOMBOY ALSO OFFERS TO GO SHOPPING WITH YOU IF YOU’RE IN THE VICINITY. COOL, EH?

What’s also cool about Mary’s services at Tailored Tomboy is that she will also be your personal style editor. Yes, she will help you go through your closet help throw out clothing that is no longer relevant, while creating new outfit ideas from existing wardrobes as well as to make a list of garments you can purchase in the future.

So over at Tomboy Tarts, we got excited and decided, Mary was the stylist we’ve always been looking for and couldn’t wait to hear more from her about the whole idea behind Tailored Tomboy and the services it provides. Check out the interview below.

Tomboy Tarts (TT): Hi Mary, it’s so nice to finally meet a personal stylist and shopper who’s doing good stuff for us tomboys who are looking for functional clothing for women that are tailored and makes us look helluva sharp. Tell us a little bit about yourself – where did you grow up, your influences growing up and how you reached this point in your life with Tailored Tomboy.

Mary Houlihan (MH): I am so happy us tomboys found one another, thank you for reaching out to me! (TT: We are too!)

I grew up in St.Louis Missouri and Kansas City. Typical American middle-class, white anglo, suburban, midwestern upbringing. My sister, Cara, who is 4 years older than me, was my biggest fashion influence. She read all of the fashion magazines cover to cover and E! Entertainment news was her religion. She would practice all of the beauty secrets and wardrobing from the magazines on me and she would always let me borrow her clothes.

Cara was not afraid to cut her hair short (think Demi Moore in the movie Ghost) and wear mens corduroys with suspenders and my Dad’s sweaters. She always tested gender lines with her dress. I, on the other hand, was very much a girly girl growing up. I attribute that to my Mom wanting to be a certain way and me abiding. I’m a people pleaser. I also have big boobs and I got them early in my life and I think that automatically made me feel like I should wear traditionally feminine clothing.

Coming out in college as bisexual and then lesbian/queer definitely changed my understanding about clothing and what it communicated about me.  Throughout my childhood I always loved clothing, style, fashion but I never understood what my style was or what it meant or why I liked it. Growing up I just wore what my sister or my friends were wearing. I didn’t think about “what works best on my body?” or “what makes me feel most comfortable or confident?” In college I started exploring all of those questions.

Like most people, my style has gone through an evolution from the way my mom dressed me, to the way my sister dressed me, to the way my friends dressed me. The reason I now dress in tomboy style is because I like the connotation to functionality, comfort and confidence. I like adding elements of masculinity to my outfits as I like to feel just a little bit butch. Although I’m sure my friends would laugh if they read that!

Tailored Tomboy Kicks Up the Dust In True Tomboy Style Fashion Tomboy Tarts

   MARY SUGGESTS ADDING MASCULINE TOUCHES TO YOUR OUTFITS TO RAISE YOUR TOMBOY STYLE CRED

TT: That’s what makes us love tomboy style. It’s a functional style for women with male vibes. With tomboy style being adopted so widely these days, just what is your take on tomboy style today as compared to past interpretations?

MH: I don’t think there has been a more exciting, all encompassing time in fashion than there is today.  It is a time of anything goes, wear what makes you feel most like you. Tomboy style is an acceptable and celebrated look. It can describe a woman in a suit and high heels or a woman in a flannel shirt and oxford shoes. It’s one word that we use to describe women who wear clothing that has traditionally been for men.

The difference today, from what I observe, is that women are wearing menswear for formal events. I think in the past it was not acceptable for women to wear pants to formal events as dresses were required for such ocassions. Now it is perfectly fine to wear pants or a suit as a woman. I think it’s very exciting.

Tailored Tomboy Kicks Up the Dust In True Tomboy Style Fashion Tomboy Tarts

   TOMBOY STYLE IS POPULAR BECAUSE WOMEN WANT CLOTHING THAT REFLECTS WHO WE ARE

TT: Who are the tomboy style icons that inspire you every single day?

MH: Ellen DeGeners, duh! The other one is Jenna Lyons – creative director and president of J.Crew. I LOVE the way she dresses and carries herself.

Garance Doré – fashion blogger, artist and photographer is also another inspiration. Garance is brutally honest and sexy and creative. Sometimes when I read her blog I cry.

 

TT: Why do you think tomboy style is so big these days?

MH: Because we are less afraid of wearing clothing that reflects who we are internally. Because women want to bend over without showing their underwear. Trust me, most of us do not want that Marilyn Monroe moment! We want to walk around in shoes that are comfortable and dance all night in them without having corns, bunions or blisters by the end of it. To me, tomboy style is freedom from conformity and discomfort. It is a form of style that really liberates women from gender norms.

Tailored Tomboy Kicks Up the Dust In True Tomboy Style Fashion Tomboy Tarts

   PULLING OFF A TAILORED TOMBOY LOOK REQUIRES PLANNING & OF COURSE, HEMMED PANTS TO SHOW OFF YOUR SHOES!

TT: Tomboys are usually portrayed as slim, androgynous types when this is not true. There are tomboys with different body shapes, sizes and styles from the very andro to the femme chic tomboys. When tailoring or styling for a client, what are some of the basic things we can all do, no matter what our body type is, to successfully pull off tomboy style?

MH: Here’s what you need to do.

#1 – Go to a high end department store like Nordstrom or Bloomingdales and get fitted for a bra, not Victoria’s Secret! Tell the person who is fitting you what you want the bra to achieve. Do you want to minimize your bust? Do you want to wear button down shirts? Do you want the most comfortable, well fitting bra you can find?

Tailored Tomboy Kicks Up the Dust In True Tomboy Style Fashion Tomboy Tarts

   TAILORED LOOKS WORK WELL EVEN THOUGH YOU ARE CURVY AS THEY ARE MADE TO FIT YOUR BODY

#2 – Find a local tailor and have all of your pants hemmed to the appropriate length and width. If you are wearing flat shoes, you should have your pants tapered at the ankle (if they aren’t already) to show off your shoes.  You don’t want your pants dragging and covering your shoes.

#3 – Fitted almost always looks better, even if you are curvy! Tailored, fitting clothing looks clean and put together. You can still be comfortable in tailored clothing, it doesn’t have to be a second skin but if you have a lot of extra fabric in your shirt or pants, have them tailored or try a size smaller, it’s makes a really big difference.

Tailored Tomboy Kicks Up the Dust In True Tomboy Style Fashion Tomboy Tarts

   EVENTUALLY MARY WOULD LIKE TO HAVE A TAILORED TOMBOY STORE WITH COMMUNITY BONDING EVENTS

TT: What is your vision for Tailored Tomboy?

MH: A storefront in Chicago’s Andersonville neighborhood where tomboys can come in and shop and get my advice. The store will sell both ready-to-wear and custom clothing. I dream of tomboys walking into my store and feeling like they would wear 80 – 100% of the inventory. I dream of it being a social space where I’ll host events and where I will meet amazing people and we will collaborate to make positive change in our community, country and world!

Tailored Tomboy Kicks Up the Dust In True Tomboy Style Fashion Tomboy Tarts

   MARY IS CURRENTLY COLLABORATING WITH THE TAILORY, NY WHO WORK WITH DANIELLE COOPER FROM ‘SHESAGENT’

TT: Cool! Now will you be collaborating with Danielle Cooper of ‘SheAGent’ from Instagram? What do you think of her style and how can one achieve such dapper-liciousness?

MH: Danielle is AWESOME! A total tomboy badass. I just signed on as a design consultant with the company that makes her custom suits, called The Tailory New York. I do think Danielle and I will be collaborating on an event in Chicago to promote The Tailory’s custom suiting in Chicago.

To achieve Danielle’s style, read her blog. Danielle has really good styling tips and clothing suggestions that range in cost from H&M to custom clothing. Danielle also incorporates both men’s and women’s clothing so you can get a sense of where she likes to buy what garments.

 

TT: Besides Danielle Cooper, are there any other collaborations that you are involved in right now or will be in the near future?

MH: The Tailory New York is currently my only collaboration. I would love to collaborate with hair salons, tattoo parlours and wedding venues. The sky’s the limit and I am just getting started!

Tailored Tomboy Kicks Up the Dust In True Tomboy Style Fashion Tomboy Tarts

   A SESSION WITH MARY INCLUDES A CHAT, SUGGESTIONS & SOLUTIONS TO ACHIEVE OPTIMAL TOMBOY STYLE

TT: Can you walk us through what a typical styling session with Tailored Tomboy is like?

MH: It always starts with a consultation.

  • Why would you like to work with a personal stylist?
  • Is this to save time? Do you have a special event? Has shopping always been a pain point for you?
  • Do you have a style icon or is there a specific look you are trying to achieve?
  • What is the most difficult garment to shop for and why?

Then I come up with a plan based on what my clients needs are. Styling with me is not usually a one time deal, we usually have a long relationship and I help my client’s with shopping for new clothing, cleaning out their closets, special events, packing for vacations etc.

 

TT: What is your personal tomboy style like?

MH: 80% of the time you will find me a in a white button down shirt and jeans. It’s my absolute favorite outfit and I always feel comfortable and confident wearing it. I have one custom suit and I cannot wait to build that collection. Truly, there is nothing like wearing a suit, especially one that was made to fit your body.

Tailored Tomboy Kicks Up the Dust In True Tomboy Style Fashion Tomboy Tarts

   MARY’S FAVOURITE TOMBOY STYLE IS A WHITE SHIRT & JEANS 80% OF THE TIME

TT: As a female entrepreneur, have you faced any challenges as a tomboy-focused stylist or even setting up Tailored Tomboy? Any wise words of advice for other women out there who want to set up their own shop?

MH: I am just starting out! So I’m very flattered to be interviewed by you and to be able to be a contributor to your blog.

Challenges, hell yeah! Mostly it is this kind of talk inside my head “can you really do this? Will you make enough money? This is really hard, you should just quit!”

My advice to other entrepreneurs:

  • Define your “why” Why do you want to start this business?
  • Read the book You are a Badass by Jen Sincero
  • Listen to the podcast Entrepreneur on Fire, hosted by John Lee Dumas
  • Find a person or a group of people who are somehow related to your field to meet with in person or online on a regular basis to keep yourself motivated, inspired and accountable to your goals

 

TT: What are some of the things that you like to do when not styling or working?

MH: My fiance and I love to walk around the city, ride bikes. Go to workout classes. Go out to restaurants. I love to read mostly self improvement and spiritual books.

 

TT: When will Tailored Tomboy be officially launching services and what can potential customers and clients expect from it?

MH: My services are available today but my website is launching on November 1st and in the meantime, if you sign up for my e-mail newsletter, you will be entered to win a free custom shirt! This is for the continental US only.


FIND OUT MORE ABOUT TAILORED TOMBOY AT THEIR OFFICIAL SITE @ www.tailored-tomboy.net
GET IN TOUCH WITH MARY TODAY FOR ALL YOUR TOMBOY STYLING NEEDS AT THIS EMAIL Mary@tailored-tomboy.net