What's your bad day backup plan?
Not every day starts off chic. Why should your outfit make matters worse?
You know those days when you wake up and the sun is streaming through the windows, birds are singing, and the smell of coffee and pancake syrup is wafting through your house?
And then you throw open your closet and all your clean clothes wink back at you from their matching hangers, and you’re immediately struck by inspiration for an outfit that’s perfectly effortless and elegant?
Lol, yeah, me either.
It’s very fun to talk about what we’ll wear on our best days, but in reality, those are the days you probably don’t need my help. But what about the ones that don’t feel quite so nice? Like Mondays, or also Tuesdays, which are just Mondays but without that new week smell?
There’s an unfair irony to the fact that, if you’re reading this, dressing nicely probably makes you feel a little better. And yet, when a day starts off yucky and gray, headachy and overscheduled, that’s when we’re least likely to reach for the good stuff.
But hold on just a second. Back away from the leggings. On this final Tuesday (yuck) in March (ick), I have a few easy suggestions to rescue your outfit and your mood.
Here are four easy outfit combinations, inspired by my real-life mood today, that you’ll want to save for later.
Embrace a billowy silhouette
Some days I simply cannot with hard clothes. However, on days when I once would’ve reached for yoga leggings and a sweatshirt, I now have a grown-up version to keep me from feeling like a hungover college kid.
The secret sauce involves an oversized button-down shirt and a pair of wide-leg pants that are, in fact, secretly leggings. (!) To create a waist without any physical restriction, I just tuck in the front of the shirt, a styling trick cribbed from Tan France during many hours of Queer Eye. If it’s really oversized, you can leave the bottom half unbuttoned and tie the two sides, or even tuck the bottom into your bra to create a little crop-top action.
A long coat and sunglasses finish this look with a chef’s kiss. Or a scowl into the afternoon sun, which is what I’m sporting today.
Dress + sneakers = cheat code
Some days I feel like I can barely put one foot in front of the other. On days like these, we need light and comfortable footwear. But actual, honest-to-god athletic sneakers threaten to drag an outfit into frumpy territory. For this, we need a billowy dress or skirt with spandex shorts underneath. I can, and have, walked many miles in this combo, which becomes secretly athletic when you add the shorts.
I’ve got a couple of oversized dresses and maxi skirts that work for this combo, and it’s wonderfully straightforward once you have it in your head that you don’t need pants to be comfy. A button-front shirt dress is an easy win, especially in lightweight cotton. For a shockingly put-together look, cinch the waist with a belt.
Put a blazer on it
I have this idea that we should re-categorize the oversized blazer and treat it like we did denim jackets in the 90s. It’s the perfect foil for dresses, jeans, and even leggings if the vibe is right. But instead of dressing down your look, like a denim jacket would, it gives you a sophisticated force-field that will hide a bad night’s sleep from prying eyes.
Mom jeans and a concert t-shirt? Meh. Add a blazer? I’ll have what she’s having. Top this combo off with a red lip for a real power move that will have you looking like a magazine editor on a Friday morning: tired, maybe, but no less intimidating for it.
I like this look with boots, but ballet flats or low-profile sneakers will work, too.
Last (but not least) resort: chic sweats
Until recently, I believed that it would be silly to spend money on around-the-house clothes. I just wore soft, but mismatched things, usually gym clothes and a sweatshirt. But then, on Black Friday, I was looking for a hooded sweatshirt to wear in the Bologna rain and found a great deal on a matching set. And I thought, why not?
Friends, for me, a matching sweatpants-and-sweatshirt set has been a weekend game-changer. Sometimes I will literally roll out of bed, step into slip-on boots and a long wool coat, and go get a coffee and some oxygen without even putting on a bra.
I wouldn’t have thought of this if I hadn’t seen some truly fabulous Italian women walking their dogs attired this way. My immediate impression was that it is simply unfair how great they look without even trying. And then I realized they were probably also really comfortable.
I like to think of this one as celebrity hangover chic. And while it may not be work-appropriate, it has a certain honesty to it that feels rewarding. I recommend big sunglasses, maybe a baseball cap, and an oversized shoulder bag for your Sunday shopping. Plus, wear an expression that says, “I would tell you all about last night if I could remember it.” Chihuahua optional.
Last stop: accessories
If you can spare a few more seconds before dashing out the door, give yourself an extra boost by putting on your favorite accessories. On days when I feel slow and grumpy, I like to reach for some little tokens of my best self, like a bracelet that matches my sister’s and a pair of earrings that remind me of hiking in the Adirondacks near my home. This is less about making the perfect outfit and more about a little self-love and emotional support, so pick what speaks to you.
Do you have a go-to outfit for days that start off on a low note? If you’ve got advice, please share it—I’ll include reader wisdom at the top of next week’s dispatch.
I love to style up a turtleneck and a baseball cap with outrageous earrings :) It makes me happy and I get to stay sooo comfy