Does this outfit make me look like a cougar?

Having a mom who has rotated the same two pairs of pants (seriously, I am not exaggerating) for the past 17 years and considers the height of fashion to be throwing a patterned button down into her collection of 15  solid colored button downs, I never learned to be a fashionista. But my mother did always stress the importance of looking put together. After all, this is the woman whose lips are permanently stained from her signature fuchsia lip color. And this is the woman who has a daughter (my sister) who won’t so much as go to the gas station without a ‘full face,’ the girl who sported fake eyelashes during her c-section so she would look her best in pictures. 

I have to admit that I did not inherit such a heightened concern for my looks. When it comes to makeup, I’m pretty low key, sticking to mascara, concealer and maybe a bit of blush. When it comes to hair, I wash it. Sometimes I dry it. But in reality, I mostly sleep on it wet, throw it into a bun or the latest DIY ponytail concoction I learned on Youtube, and go. And when it comes to my clothes, I stick to the basics. Most people would probably label me preppy. You can usually find me in skinny jeans, riding boots, Oxford shirts, and a cardigan or crew neck sweater, with some variations here and there. I love my pearl earrings and necklace, often rotate between 3-4 key pieces of jewelry (though my jewelry box is full of unused gifts, bargains from Francesca’s that I swear I’ll wear someday, and hand-me-downs from my mom that I just can’t get rid of). Sometimes if I’m feeling ambitious, I’ll even mix in a statement necklace because…well, big girl = big necklace. When you’re 5’10, you have to embrace the few perks of being average male height. 

On the whole, I tend to take fashion and trends in stride. Actually, I tend to stray away from trends, especially if they don’t get along well with my body type. I will only incorporate a trendy piece or two if it’s a) unavoidable b) super cute c) on sale and/or d) makes me look skinny. So, as you can imagine, I’ve always had some difficulty in piecing together ‘going out’ outfits. Most of my clothes are far too preppy for a night out at the bar. And after having built a teacher wardrobe for years, I refuse to wear such items out on the weekend, no matter how versatile they may actually be. I just can’t. My teacher clothes make me feel sexless and old. 

In college, combatting this ‘what to wear when I go out’ problem was pretty easy. I simply threw on my standard pair of boot cut jeans, slipped on my ‘frat’ shoes (the one pair of crappy old black boots I didn’t mind sending into battle with beer, vomit and urine), and wedged into one of my standard ‘boob’ shirts from Old Navy or H&M.  Boob Shirt: a tight top, usually V neck, best used for procuring free beverages and phone numbers. When the weather was nice, I really shook things up and exchanged my jeans for a mini jean skirt. 

But deciding what to wear out post college has been an ongoing conundrum, one that gets more difficult with each passing year. The first problem is that I find there’s a lack of stores that cater to my particular age range. I’ve outgrown (literally and figuratively) former go-to places like Forever 21 for cheap yet cute bar wear, and sadly Express and the like have gotten a bit too tight, a bit too clubby…and okay I’ll just say it, a bit too slutty. So that leaves me with the Loft and the Gap and Banana Republic and JCrew—all great stores that I frequent for my clothing, but clearly they aren’t the leading designers for night life apparel. I’m sure there are many yet undiscovered little boutiques with some great options out there for me, but I’m also pretty sure that I can’t afford them. 

And then there’s always the question of where I’m going. What may start off as a casual night at at a nondescript restaurant/bar may then turn into a quick stop at the Irish Pub to hear a great cover band, and then a jaunt to the young, college-esque bar down the street, followed by a club because it’s 12:30am and I’m in the mood to dance after that last drink. Especially now that I’m living in a major city, I find it challenging to dress for the right type of place because there are so many different options and they’re all within walking distance. Too, no one ever makes set plans, and even when they do, these plans change based on the line to get it, how dead the bar is, and how many drinks we’ve all consumed. So dressing for the unexpected can be difficult, which can be furthered complicated by the winter. I know it’s not sexy to wear my preppy riding boots and a cardigan, but I’m cold, and I’m not about to climb over that snow pile to get into the cab with my suede heels on. 

Problem Three: I’m at an awkward age, and I’m self conscious about it. I’ve finally accepted that I can’t pull off the little outfits that the girls into their early 20s are wearing. And I’ve even accepted that I’m okay with being slightly older. But I don’t want to look older. This means that I can’t try to imitate the fashion of those in their early 20s. I have to try something else, something that is age appropriate yet screams that I’m still young and fun. However, when you try to find this ‘I’m young and sexy, but I know I’m not too young and I’m okay with that’ look, you run the risk of imitating another fashion label—the cougars. You know, those women in their 40s and 50s, the women who are divorced or still single or getting their once a year girl’s night out. You can spot them by their uniform—they’re usually pretty skinny and quite fit, rock a great pair heels with dark wash skinny jeans, a tank top, and a blazer/snug jacket-like looking thing. They have great accessories because they’re in their 40s and can afford the nicer purses and jewelry. Simply put, they look fantastic…and older. The tank top/blazer combo gives it all away. As does any leopard print, leather accents, or a White House Black Market label. So we single ladies in our 30s are stuck somewhere in between. We fear looking like we’re wayyyy too old to be in this place, but we don’t want to look like we’re trying too hard to fit in—or that we haven’t gotten the memo that we graduated from college in the old days…before Twitter. 

So what’s a girl to do? Where’s a girl to go? Is it too much to ask for a store to cater to our age group? All we want is an affordable, yet not cheap-looking option that can fit into the night life. Something that is made for actual women who have curves and bumps and makes us feel and confident and dare I say sexy. Something that lets us blend in and leaves people wondering just how old…err young….we are. There has to be something out there—something in between the micro minis and the leopard blazer. 

If you find it, let me know.