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The Perfect Outfits for All Your Toughest Situations

"Oh, I know exactly what to wear to meet my ex," said no one ever.

By Chelsea Peng

Mar 16, 2016

Courtesy, design by American Artist

Few things are worse than knowing you have to look good, buckling under the pressure of having to look good, then showing up looking—and more importantly, *feeling*—less than good. Because the only way to avoid a serious #fashionfail is to pray for deliverance (good luck) or plan ahead (ugh, FINE, Mom), we've put together five exemplary outfits for five of life's hardest-to-dress-for situations.

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A full day outside during which anything could happen

<p>They're statistically most liable to happen in the summer (just ditch the topper then), but for *any* Saturday or Sunday spent aimlessly traipsing around, opt for denim, a classic shirt with some added visual interest, walkable heels, and accessories that might just catch someone's eye if you end up at a bar nine hours later.<br></p><p><br></p><p>1. Pixie Market bell-sleeve top, $92, <a href="http://bit.ly/1RkTmf1">pixiemarket.com</a>.
</p><p>2. Shrimps jacquard coat, $765, <a href="http://bit.ly/252Y7E4">shopbop.com</a>.
</p><p>3. Levi's Re/Done jeans, $256, <a href="http://shopredone.com/collections/straight-skinny-size-27/products/no-27ss127533nd">shopredone.com</a>.
</p><p>4. Cuyana suede and leather saddle bag, $295, <a href="http://bit.ly/1RkTtqR">cuyana.com</a>.
</p><p>5. Miss KG mid-heel Mary Janes, $85, <a href="http://bit.ly/1U5ucI9">asos.com</a>.
</p><p>6. Graziela diamond double ear cuffs, $270, <a href="http://grazielagems.com/product/double-curve-ear-cuffs-in-rose/">grazielagems.com</a>.
</p>

Courtesy, design by American Artist

They're statistically most liable to happen in the summer (just ditch the topper then), but for *any* Saturday or Sunday spent aimlessly traipsing around, opt for denim, a classic shirt with some added visual interest, walkable heels, and accessories that might just catch someone's eye if you end up at a bar nine hours later.

1. Pixie Market bell-sleeve top, $92, pixiemarket.com.

2. Shrimps jacquard coat, $765, shopbop.com.

3. Levi's Re/Done jeans, $256, shopredone.com.

4. Cuyana suede and leather saddle bag, $295, cuyana.com.

5. Miss KG mid-heel Mary Janes, $85, asos.com.

6. Graziela diamond double ear cuffs, $270, grazielagems.com.

Rain

<p>Fact: Cloud juice falling from the sky is very sad-making nine times out of 10, so the best way to remedy this is to pretend you are the heroine of a Victorian novel but not the frail kind that needs a fainting couch. Futuristic mirrored boots, mixed florals, and a utilitarian jacket keep things modern.<br></p><p><br></p><p>1. Zara lace dress, $100, <a href="http://www.zara.com/us/en/woman/dresses/view-all/dress-with-lace-and-frill-c719020p3402512.html">zara.com</a>.
</p><p>2. Veda trench coat, $425, <a href="http://bit.ly/254nju7">thisisveda.com</a>.
</p><p>3. Dorateymur mirrored-leather ankle boots, $490, <a href="http://bit.ly/1S4ghhP">net-a-porter.com</a>.
</p><p>4. J.Crew painted leather bucket bag, $118, <a href="http://bit.ly/1RkXGRL">jcrew.com</a>.
</p><p>5. New Look frilled umbrella, $14, <a href="http://bit.ly/1TOjgya">asos.com</a>.</p>

Courtesy, design by American Artist

Fact: Cloud juice falling from the sky is very sad-making nine times out of 10, so the best way to remedy this is to pretend you are the heroine of a Victorian novel but not the frail kind that needs a fainting couch. Futuristic mirrored boots, mixed florals, and a utilitarian jacket keep things modern.

1. Zara lace dress, $100, zara.com.

2. Veda trench coat, $425, thisisveda.com.

3. Dorateymur mirrored-leather ankle boots, $490, net-a-porter.com.

4. J.Crew painted leather bucket bag, $118, jcrew.com.

5. New Look frilled umbrella, $14, asos.com.

Festivals (when you are not a celebrity who gets driven around)

<p>During the day, pull the top of the jumpsuit down and tie the arms around your waist. (Fist-pumping and going to the bathroom are so much easier that way.) When night falls, wear it as the designer intended and whip out your personalized lighter for a little, uh, recreation.
</p><p><br>
</p><p>1. Aritzia striped tank, $30, <a href="http://us.aritzia.com/product/kendall-tank/50498.html?dwvar_50498_color=1846">aritzia.com</a>.
</p><p>2. Karen Walker color-block sunglasses, $300, <a href="http://bit.ly/252WK8G">shopbop.com</a>.
</p><p>3. Hadjio toile boiler suit, $279, <a href="http://hadjio.com/collections/hadjio/products/red-toile">hadjio.com</a>.
</p><p>4. Frances Valentine leather tote, $625, <a href="https://francesvalentine.com/shop/medium-charlie-metallic-leather-top-handle-tote-slv-camel">francesvalentine.com</a>.
</p><p>5. Pumpkin Seed Jewelry custom lighter, $32, <a href="http://bit.ly/1UekGC1">etsy.com</a>.
</p><p>6. Vans SK8-Hi Slim sneaker, $55, <a href="http://www.vans.com/shop/shoes-classics-sk8-hi-slim/sk8-hi-slim-blanc-de-blanc-blanc-de-blanc">vans.com</a>.</p>

Courtesy, design by American Artist

During the day, pull the top of the jumpsuit down and tie the arms around your waist. (Fist-pumping and going to the bathroom are so much easier that way.) When night falls, wear it as the designer intended and whip out your personalized lighter for a little, uh, recreation.

1. Aritzia striped tank, $30, aritzia.com.

2. Karen Walker color-block sunglasses, $300, shopbop.com.

3. Hadjio toile boiler suit, $279, hadjio.com.

4. Frances Valentine leather tote, $625, francesvalentine.com.

5. Pumpkin Seed Jewelry custom lighter, $32, etsy.com.

6. Vans SK8-Hi Slim sneaker, $55, vans.com.

Business casual, whatever that means

<p>If no one knows what this means, WHY IS IT A DRESS CODE? Should you find yourself in the company of people who toss "business casual" around like it is not a fallacy (😑), stay squarely in your lane with a drape-y shirt and dark pants but not so squarely that your top can't double as pajamas, the trousers can't unbutton into kick flares, and the accessories can't signal to the only other cool person there that you both need to leave immediately.
</p><p><br>
</p><p>1. Mango double-breasted blouse, $60, <a href="http://bit.ly/254r0Qk">shop.mango.com</a>.
</p><p>2. EyeBuyDirect glasses, $70, <a href="https://www.eyebuydirect.com/prescription-glasses/acetate-eyeglasses-prism-translucent-p-15897">eyebuydirect.com</a>.
</p><p>3. & Other Stories croco-effect leather bag, $195, <a href="http://bit.ly/1ST0i8G">stories.com</a>.
</p><p>4. Hómini Studio silver earrings, $240, <a href="http://www.hoministudio.com/collections/caravanas/products/secret-circle-earring">hoministudio.com</a>.
</p><p>5. Liebeskind croco-effect leather tote, $260, <a href="http://usa.liebeskind-berlin.com/Chelsea/216.420.94.8138,en_US,pd.html?sku=216.420.94.8138.2900.1&cgid=ta_shopper&ref=lp&is=true">liebeskind-berlin.com</a>.
</p><p>6. Zara leather heels, $119, <a href="http://www.zara.com/us/en/woman/shoes/view-all/leather-high-heel-sandals-c719531p3230653.html">zara.com</a>.
</p><p>7. Trademark front-slit pants, $348, <a href="http://bit.ly/1Z0N0Yg">trade-mark.com</a>.</p>

Courtesy, design by American Artist

If no one knows what this means, WHY IS IT A DRESS CODE? Should you find yourself in the company of people who toss "business casual" around like it is not a fallacy (😑), stay squarely in your lane with a drape-y shirt and dark pants but not so squarely that your top can't double as pajamas, the trousers can't unbutton into kick flares, and the accessories can't signal to the only other cool person there that you both need to leave immediately.

1. Mango double-breasted blouse, $60, shop.mango.com.

2. EyeBuyDirect glasses, $70, eyebuydirect.com.

3. & Other Stories croco-effect leather bag, $195, stories.com.

4. Hómini Studio silver earrings, $240, hoministudio.com.

5. Liebeskind croco-effect leather tote, $260, liebeskind-berlin.com.

6. Zara leather heels, $119, zara.com.

7. Trademark front-slit pants, $348, trade-mark.com.

Meeting someone unpleasant and/or seeing your ex

<p>Sweats are the ultimate sartorial diss, but they leave an opening for "Are you okay?" which we simply cannot have. So just as trust-fund bros wear <a href="http://www.gentlemansgazette.com/go-to-hell-pants/" target="_blank">go-to-hell pants</a>, you should go for a loud, Chloë Sevigny-ish outfit with the mindset of "If you don't like it, you can GTFO." </p><p><br>
</p><p>1. Charlotte Simone shearling bomber jacket, $660, <a href="http://bit.ly/1STcqpX">matchesfashion.com</a>.
</p><p>2. Urban Outfitters unicorn hair clip, $12, <a href="http://bit.ly/254zbvZ">urbanoutfitters.com</a>.
</p><p>3. Title A ruched dress, $550, <a href="http://bit.ly/1LqSIR6">net-a-porter.com</a>.
</p><p>4. Shoko for Meli Melo leather bag, $637, <a href="http://bit.ly/1S4sQtp">melimelo.com</a>.
</p><p>5. Frances Valentine metallic leather sandals, $495, <a href="https://francesvalentine.com/shop/beatrix-metallic-leather-sandals-gold">francesvalentine.com</a>.</p>

Courtesy, design by American Artist

Sweats are the ultimate sartorial diss, but they leave an opening for "Are you okay?" which we simply cannot have. So just as trust-fund bros wear go-to-hell pants, you should go for a loud, Chloë Sevigny-ish outfit with the mindset of "If you don't like it, you can GTFO."

1. Charlotte Simone shearling bomber jacket, $660, matchesfashion.com.

2. Urban Outfitters unicorn hair clip, $12, urbanoutfitters.com.

3. Title A ruched dress, $550, net-a-porter.com.

4. Shoko for Meli Melo leather bag, $637, melimelo.com.

5. Frances Valentine metallic leather sandals, $495, francesvalentine.com.

Chelsea Peng I'm Chelsea Peng, the assistant editor at MarieClaire.com.

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