Face Your Fears: "Going-Out" Edition

The gym requires gym clothes, big presentations necessitate your Business Boss skirt, and your after-hours activities — you know, bar hopping, Tinder meet-cutes, dance offs — call for a uniform that lets you not only present your most attractive, confident self, but provide the ability to shimmy freely, laugh unselfconsciously, and run around comfortably. The perfect going-out look is truly performance wear in that it combines function, fashion, and sass in equal measure. And, when you've got the wrong one on, it can make your whole night a bust — there’s no bigger buzzkill than sore feet and a dress that pinches, or that nagging feeling that you’re in costume.
Because it's such a tricky category, your going-out wardrobe is most likely the culmination of years of trial and error, and you’re probably unwilling to upend all that research. But, if you haven’t shaken things up in awhile, it might be time to think about ways you can express a new side of you, without feeling like not you. To help you reconsider your long-held dressing beliefs, we found five party-loving women at Refinery29 — each deeply entrenched in her own signature look — and asked them to confront the styles they think they can't wear. In the process, we introduced them to new opportunities to make their social butterflying a lot more satisfying, and we hope we've inspired you to try on some new wings, too.
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Connie Wang, style director

Fear: Body-con
The Fear Talking: "I like my body, and I like getting gussied up for nighttime (which might be surprising to anyone who only sees me in the daytime, in my standard uniform of big pants and silly tops). However, my biggest fears stem from being uncomfortable and being invisible. There's something about a body-con dress that just makes me feel like one of a million...while paradoxically also making me feel completely exposed in a 'hey guys, you can see my bellybutton through my dress' way.

"I'm not scared of short, tight, or low — just not all at once, and with a twist, please."
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The Reasoning Behind The New Look: The reason body-con can be so terrifying is that it shows off every curve, divot, lump, and bump on your body. Pair that with a short hemline and a low neckline, and you've got yourself a challenging situation. To make it feel more accessible — not to mention cool — we put a T-shirt on underneath. It's one of our favorite strapless-dress styling tricks. Not only does it help temper all that snugness, but it also makes the look less expected.

Says Connie: "When Emily pulled out that top dress, I made a fear noise. It was white, very short, strapless, and about the width of a handtowel. But, worn with a jersey T-shirt underneath, it was a surprisingly cool match-up that felt as unexpected as my typical 'going-out' wardrobe of weird skirts and tiny tanks. While I probably would choose a different color next time (white just isn't very practical for someone who can't walk without spilling her drink), I'd definitely do this again with a bold print."

Jonathan Simkhai shirt, Connie's own shoes.
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Taylor Bryant, beauty production assistant

Fear: Covering up
The Fear Talking: "My go-to outfit for nights out typically includes either a semi-revealing skirt paired with a tank top, or something that shows just enough skin. If I'm really feeling myself, I'll venture into the wonderful world of skintight dresses. (American Apparel body-con dresses used to be my jam.) Bodysuits are also put into rotation quite frequently. I gravitate toward these items mostly because, sartorially, during the day, I'm more of the laid-back type, and nighttime gives me a chance to really hone my fancier, show-off-my-body side. As B would say: If you got it, flaunt it.

"My fear is being too covered up when going out. So, essentially, wearing baggy clothes that hide the shape of my body. What makes my fear so scary is, I guess, having people think that I just rolled out of bed and put on the first thing I found in my closet. Sure, every girl wants to look like they didn't try hard when it comes to their clothes, but not like they put little to no effort in looking presentable."
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The Reasoning Behind The New Look: Covering up doesn't have to mean looking lazy, and both the pieces we put Taylor in are polished, pretty, and sophisticated — without feeling so serious. While we don't recommend going hard on the dance-floor in a sweater, a cropped knit looks great with a flippy, ready-for-action long skirt.

Says Taylor: "I felt hot in my final outfit. The top is definitely something I would wear in my everyday — the boxy, two-sizes-too-big look is definitely my daytime thing (I'd probably pair it with an equally slouchy pair of boyfriend jeans). But, it's not so much when I'm going out. The skirt, also, wasn't really my personal style. With that said, although I don't think I would wear these pieces out in the future, I do think the two pieces worked surprisingly well together and, even though it wasn't my cup of tea, I definitely think it would look cute on somebody else.

H&M top, Taylor's own shoes.
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Zooey Purdy, product manager, publishing platform

Fear: Color
The Fear Talking: "My go-to outfit for a night out is usually a pair of fitted black jeans (I play with the texture — so leather, ripped, coated, etc.) and an extra-large sheer black or white T-shirt (if I need to be dressier, this will be an oversized silk button down). I then pair this with loads of silver jewelry. I feel comfortable in this outfit for a few reasons. 1) I know I can eat and drink as much as I want without concern about a food baby showing. 2) I prefer to wear pants so that I can sit cross-legged or with my feet up without worrying about flashing anyone. 3) It's easy and classic with a bit of grungy edge.

"So, I have a fear of color. Or maybe more accurately, I have an extreme love for all things monochromatic. It just feels so clean and classic. I love the look of a mix of textures that are all the same color. Moreover, ever since I discovered that I feel my best in all neutrals, I never turned back. I just don't feel like myself anymore when I wear color. I guess that's part of the reason I dressed so colorfully on Halloween — it was fun to do once and feel totally out of character. Immediately afterwards, though, I needed to hibernate in a sea of all-black to regain my sanity."
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The Reasoning Behind The New Look: There's no reason that color shouldn't have as much of an impact as black-and-white, especially in a strong, single hue. We chose a cobalt blue for Zooey in an avant-garde shape she typically gravitates toward. Deep, saturated jewel tones can be as serious-feeling as black, but a little more fun.

Says Zooey: "There's something about color that feels overly enthusiastic to me? I can't really explain it. My biggest fear is definitely looking like a clown; I already wear a lot of oddly shaped garments, and adding a bunch of color to that makes me feel clown-ish. But, I would totally wear this look...in black. And, with black shoes."

Delfina Balda dress.
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Kelsey Miller, senior features writer

Fear: Sexy
The Fear Talking: "I get a little anxious when I'm dressed up in something that feels attention-grabbing. I'm not generally an on-trend kinda gal, and that's fine. But, when you put on an outfit that says 'look at me!' you want to be confident in that outfit. And, this is an area I'm just not super confident in.

"Growing up a not-so-skinny girl, I remember trying to dress up all cute for birthday parties and getting laughed at. I know, cue the violins. But, though I've come a long way in terms of body acceptance, there's still a voice in my head that sometimes pipes up and says, 'You're trying too hard and it's obvious. Go home before you embarrass yourself.'

"But, that voice is a jerk and I try not to do what it says. So, here I am."
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The Reasoning Behind The New Look: Off-the-shoulder is one of the biggest trends this holiday season, and should be one of the first silhouettes you try out, if you're a woman who can get away with a strapless bra all night. This particular dress still has sleeves and a longer, fuller skirt, but that flash of shoulder is so, so hot.

Says Kelsey: "I love this dress so much. It's incredibly comfortable, super flattering, and shows off my shoulders. I totally forgot about them, and they're great! Also, hey boobs! It's crucial to find a dress that highlights something you like about yourself. That's the confidence key. I would absolutely wear this dress out again (which is why I begged and pleaded to keep it)."

Kelsey's own tights.
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Katie Gowdy, senior fashion sales director

Fear: Flats
The Fear Talking: "I rarely wear flats to begin with, so to wear them out at night would be completely outside of my comfort zone. I've never liked wearing flats, and I actually find them more uncomfortable than heels. I'm only 5-foot-5, and most of my family and friends are tall, so I like a little height when I go out. Also, my go-to outfit for a night out in the fall typically involves jeans a leather jacket, heeled booties or a great pump. I feel most comfortable in jeans and heels because, while jeans are casual, a heel can always dress up the look."
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The Reasoning Behind The New Look: For some women, heels are akin to body armor. From years of walking on an incline and feeling comfortable seeing the world at a certain height, being put in flats is like literally being knocked down a few notches. Katie doesn't own a single party-time flat, so when looking for a shoe that'd work for her, we focused on a silhouette she already loves: the pointed pump. Without the heel, it's super important to make sure the point is delicate and not too long (otherwise, you'll trip over them constantly). Without having to balance on the balls of your feet all night, you won't have any problem staying out until last call.

Says Katie: "Wearing flats definitely let me go a little dressier with my clothes, and this dress was a departure from my usual jeans look. I usually stick to darker colors, so a pink dress and sparkly flats were something I'm not really used to. I liked how feminine the final outfit was, but I'd probably go with a more neutral color palette in the future. I liked how long the flats made my legs look (especially with the pastel dress), but I don't know if I'm ready to give my heels up quite yet!"

Tibi dress, Katie's own leather jacket.