{sneakers, leather pants, and wild hair – standard NYC uniform}

Happy Friday! Today’s question comes from a reader curious about my personal style…something I probably don’t share enough about, though I’m working to get over myself a bit and do more of that moving forward. Also, it gave me the chance to talk about Wisconsin, and you know I love doing that.

Matthew asks:

Where did you grow up, and what effect did your surroundings have on forming your sense of fashion?

Great question, Matthew!

I believe super-strongly that your hometown influences your personal style.

For those of you who didn’t know—and I can’t believe anyone still wouldn’t…I’m pretty sure Style Girlfriend ranks higher with Google for “cheese curds” than “men’s style” by this point—I hail from the land of dairy and wonder, better known as Wisconsin.

There, I spent eighteen idyllic years in Madison, the state capitol, before gtfo‘ing it for NYC and the east coast.

I lived in Manhattan for a year before college, manning the front desk at a high-profile hair salon. A very unglamorous job in a very glamorous industry.

That gap year was amazing for 1) giving me a much-needed break from the rigors of a pretty demanding high school course of study, and some time to reflect on what I actually wanted to study in school, and 2) exposing me to the city in a way that my only other contact with the Big Apple—a weekend trip here with my dad at age thirteen—really hadn’t.

Certainly not enough time to know not to call it the Big Apple, or that staying in Times Square nearly nullifies a visit.

When I landed at school in Pennsylvania the next year, I jumped in with both feet and a backpack full of books. I studied my ass off, which I don’t think I would have done so vehemently if not for the prior year spent in an hourly, unskilled job.

After decamping to a big school in a tiny town for four years (well, three..I spent junior year abroad), I’ve been back here ever since.

{baseball hat and bling – typical high/low mix}

The impact that my Midwest upbringing, and to a lesser extent, my time in Nowheresville, College town USA, had on my style here in New York is this:

As an adult is that I’m confident and comfortable being different.

In Wisconsin, I was always the oddball, which is why I was so attracted to New York in the first place. It’s a city chock full of expat oddballs.

Thankfully, growing up I was surrounded by friends and family who loved me and indulged my forays into fashion, for better or for worse.

And trust me, some of them were definitely for worse.

Which meant that, while I sometimes felt very odd man out growing up, I also felt extremely free to try what I wanted, knowing that while I may get an eyeroll or two, no one would love me any less for dressing just a little bit different.

{Red, Blue, and Grey}

Because let’s be real: Wisconsin is not known for pushing the fashion limits.

I often say that if you played “Drink every time you see someone wearing a Badgers or Packers apparel” in Wisconsin, you would be flat out on the floor in about five minutes. It’s crazy, and I notice it more and more every time I visit. Mostly because I own zero Wisconsin gear (In my defense, I didn’t go there! And I don’t look that good in green or gold.)

Everyone at my the dinner table right now is wearing UW gear, including my 2yr old niece and my 3-mo old nephew #Wisconsin

— Style Girlfriend (@StyleGF) October 14, 2012

Growing up, I was the one putting her hair in little buns like Gwen Stefani from No Doubt. Or wearing a dress over pants (which I still think looks cool).

I wasn’t an outcast by any means, but among my friends I had the reputation of being the sartorial wild card – more likely to be found wearing a bandana and hoops like Julia Stiles in Save The Last Dance than a hooded sweatshirt from the Gap.

Which was fine. I liked being different—I still do—and it forced me to become more confident in my personal style.

The way I saw it: I liked what I liked and so what if other people don’t get it?

I think now that’s why I’m so adamant with you guys that YES it’s okay to dress up more than your peers, and YES it’s okay to make an effort to up your style game even if it pushes you out of your comfort zone, and even if  the results aren’t always perfect.

Owning your own personal style is empowering when it makes you feel more like YOU.

{“Working From Home Today” style}

It’s funny, now that I’m out here in New York, I’m actually pretty conservative compared to a lot of people here (especially those who work in fashion).

Or at least, I think so until I visit my family, and they tease me for the bright red lipstick on my face for breakfast at Original House of Pancakes.

In that way, I don’t think New York has changed my style, but I do think it’s given me more of an outlet to try fashions and trends that would get me that “Oh Megan” reaction from friends and family back in Wisconsin.

Because, whatever, I look awesome in a bright red lip. Just like, wherever you are, you probably look awesome in a slim cut, two-button suit. Or chukka boots. Or skinny jeans. Or with a little product in your hair.

The other lasting effect of growing up in Wisconsin?

I’m very (very, VERY) conscious of what I spend on clothes.

Dropping an exorbitant amount of money on clothes was just not a thing – not in my household, and not among my friends, so it’s been a journey for me to acknowledge that, yes, it’s worth spending a little more on items that will last you forever.

While I’ll always love getting a deal at Target, I know that investing in beautifully-made clothing and accessories is just that: an investment. I’ll never spend crazy amounts of money on all my clothes, but some things? I’m willing to accept an extra zero on the price tag.

That’s why you can be sure that when I recommend you buy something—shoes, a suit, a cashmere sweater that makes your eyes bug out of your head a little—it’s not done so lightly.

I wouldn’t spend money on something I didn’t think would really go the distance for me, and I wouldn’t tell you to do so either unless I really believed it was a worthwhile way to spend your hard-won discretionary income.

So the short answer, I guess?

Growing up a cheapskate weirdo in Wisconsin made me a confident, tightwad cool kid in New York.

TELL ME:

HOW DID YOUR HOMETOWN INFLUENCE YOUR PERSONAL STYLE?