The outfits 14 stylish people choose for a pick-me-up on a no good, very bad day

May 21, 2019 at 12:27PM by CWC

“Never underestimate the power of a good outfit on a bad day.” It’s one of those maxims that end up on inspirational Pinterest pages and coffee mugs, despite hazy origins, because it’s just so true for so many people. Sometimes, you are what you wear, and that can be especially useful when you’re not feeling like yourself.

I asked 13 stylish folks about the good looks they rock in the hopes of generating good vibes, and here’s what they had to say.

clothes and confidence
Photo: Keri Goff

“When it comes to my anxiety, fashion and function collide. I fortify myself in layers—in this photo there are four, not to mention the double option of a dad hat and a beanie. A flight, a road trip, a date, a day when I don’t know exactly where I’ll end up or when I’ll be home: If I’m unsure about the situation, I dress for every situation. If I’m unsure about the temperature, I dress for every temperature. And sure, all those anticipatory concerns are largely unfounded, but strangers often tell me they dig the jacket, and I dig the comfort of wearing everything underneath it. On those worry-filled days, I definitely appreciate the peace of mind… and a little validation, too.” —Ben Kassoy, author, Editor-in-chief of

clothes and confidence

“I love to wear this dress as much as I can to auditions, especially those I’m feeling a bit ‘meh’ or nervous about. It gives off a fun and friendly vibe and I almost always get complimented on it, which is a nice icebreaker when walking into a room of people who are about to judge my work. It feels a bit like protective armor. Like, come on, you gotta love the girl in the cute dress, right?!” Kristen Alyson Browne, actress, singer, dancer

clothes and confidence
Photo: Traci Elaine

“Jewel tones and shoulders, baby. Color moves mood. I love bold, striking, rich colors that make a statement and wake up your damn senses. I’ve gotten so many compliments and conversations from the electric blue of these pants. I also love unexpected lines like an off-the-shoulder bodysuit that I’ve paired with it. When I wear an outfit like this I feel ready to bop down the street to my own beat. It sets my day up for whimsy, wonder, and playfulness that will keep me awake and connected.” —Christina Blacken, founder of The New Quo

clothes and confidence

“This outfit makes me feel bold and confident, maybe because of the colors. Also, I feel comforted because of the weight of the jacket, and the comfort in turn makes me feel poised and ready. Most of the clothing is from Banana Republic. I never thought that I would go for a professional look as my bad day outfit, but it works for me!” —Julio Medina, dancer and choreographer

clothes and confidence

“When I’m having a bad day, I seek two things: comfort and power. Wearing a sweatshirt makes me feel effortlessly cool, like I have everything under control. Adding this combination of accessories that remind me of the powerful women in my life gives me inspiration and makes me feel like my team has my back, no matter what. This outfit makes me feel like I have the confidence to make a decision, the softness to admit vulnerability, and the edge to allow both those things to be true at the same time.” —Farah F. Sheikhmarketing professional, nutrition and fitness enthusiast

clothes and confidence

“What I thought I needed from a ‘bad day’ outfit was something dark, but wearing that made me feel worse. I realized instead I needed bright clothing that makes me feel sunnier, that I have a fond connection to. This look is incredibly me—vintage and modern pieces in both classic and unusual styling. It makes me feel like the best, most authentic version of myself, which I need to remind myself of when I’m feeling low. I feel elevated wearing it, and it makes the gray days much brighter.” —Elyssa Goodman, writer, photographer

clothes and confidence

As a way to be cheeky, on bad days, I like to wear my SAD BOY sweatshirt; not so much to wallow in feels, but to make light of the situation and wear where I’m at with pride and acknowledgement. And also because it’s literally the most comfy shirt I own. It also always makes someone laugh, which brightens my mood. I like to wear my lavender circular glasses on bad days to bring some color to the grayness of the day and to channel my inner diva, Elton John- or Janis Joplin-style. I don’t normally wear all black (even though I’m a born-and-raised New Yorker), but when I’m feeling down, I like to feel sleek, and let the bit of color I do wear pop (canary yellow hat matched with my bright hair).” —Rex Renee, performing artist, writer

clothes and confidence

“Don’t we all need a ‘bad day’ outfit? I wear solid colors and lots of accessories. Usually a top hat, shades, and statement accessory. As of recent, I’ve been doing a lot of scarves and ascots. Outfits like these gives me my super powers back.” —Tony Triumph, branding and media strategist, writer

clothes and confidence
Photo: Keri Goff

“On a bad day, I’m thinking reliable look and comfort. I’ve been rocking an iteration of those Levi’s now for over a decade. The Reeboks are comfy and a classic. And an all-black outfit helps a little bit of color, even if it’s just a non-branded maroon beanie pop. Cozy steez. Looking good and being proud of the outfit I put together has always made me feel a little more confident in the world. It’s important for me to be seen, not in the sense of needing attention, but for folks to get a sense of who I am. Even without talking to someone, how I dress feels like a part of my authentic expression of self.” —Aaron Leven

clothes and confidence

“For me, a jumpsuit is the ultimate outfit. It lets you go from day to night and feel fancy but still powerful. Black ensures that no matter how many coffees I spill on myself, I still look put-together. Sneakers are my go-to and I love a pair that makes me feel cool, not sloppy. The statement jacket brings the fun and warmth so I’m prepped for any chilly office environment (which is usually where my bad days occur). When I dress comfy, cool and creative, I FEEL more comfy, cool and creative.” —Lyndsey Wheeler, founder of Perchance

clothes and confidence

“You’ll *never* see me in sweatpants… my college friends used to call me out on always looking put-together, even during finals. So if you see me in athleisure wear, it’s fair to assume that I’m not feeling my best self. To me, just like that saying, ‘You should put a smile on your face before walking out,’ extends to my outfit. Fashion has always given me an extra boost of confidence and energy. But having this outfit on means that I didn’t even try and I just feel like I’m in a slump all day.” —Sarah Kim, journalist, advocate, multimedia producer

clothes and confidence

“I fly a lot for work and also enjoy exploring new cities during the weekend, so a bad day for me often involves a long travel day. Layers are key! The Jordans are a great conversation starter, too. They bring an extra boost of energy, feeling like I can attack the day. Comfort always comes first for me on a bad day, but this outfit also gives me confidence that I can wear it in most settings. It’s versatile so I can either fit in or stand out—the choice is mine.” —Daniel Essman, financial advisor

clothes and confidence

“I’m not sure if we’ve moved closer to the sun or if the sun has moved closer to us here in Nigeria, but a pair of sunshades and sandals are a MUST for such heat-filled days, and the shades also help me avoid people’s eyes because I wouldn’t want to chit-chat with many people on a bad day. If I know a day is going to suck, I’m not sure I’d have much enthusiasm to even go out, so wearing these simple things make me feel much better, especially with my bone neck-piece and a few hand beads for good luck.” —Mirabelle Morah, Editor-in-Chief and communications head for BlankPaperz

“When I’m having a bad day, I like wear something that I think Vincent Van Gogh would have worn back in the day. It makes me feel creative. Also the ruggedness and functionality of Western/workwear makes me feel like I can tackle anything the day might throw my way. For me, a solid outfit can be a bit of a super power that gives me confidence when I’m not feeling great about myself.” —Andrew Cooper, digital marketer

On the Well+Good team, one editor turns to a power blazer when she needs a pick-me-up, while another reaches for a fringe skirt.

Continue Reading…

Author Ben Kassoy | Well and Good
Selected by iversue

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