5 Work Wardrobe Challenges, Solved
1/34Gallery Owner: The Challenge
Your art-school days are long behind you — and now that you’re hob-nobbing with collectors all day, those paint-spattered jeans you lived in senior year won’t do.
![<p>Make tailored-but-statement-making pants the center of your look. Then pair them with polished accessories and a distressed jean jacket to keep the look decidedly downtown.</p>]()
2/34Gallery Owner: The Solution
Make tailored-but-statement-making pants the center of your look. Then pair them with polished accessories and a distressed jean jacket to keep the look decidedly downtown.
![<p>Maison Margiela Embroidered Velvet Flared Pants, $1,330, <a href="http://www.net-a-porter.com/us/en/product/607472#" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
3/34Maison Margiela Embroidered Velvet Flared Pants
Maison Margiela Embroidered Velvet Flared Pants, $1,330, net-a-porter.com
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![<p>Valentino Layered Silk-Georgette Blouse, $1,490, <a href="http://www.net-a-porter.com/us/en/product/608427" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
4/34Valentino Layered Silk-Georgette Blouse
Valentino Layered Silk-Georgette Blouse, $1,490, net-a-porter.com
![<p>Saint Laurent Cropped Distressed Denim Jacket, $1,490, <a href="http://www.net-a-porter.com/us/en/product/608796" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
5/34Saint Laurent Cropped Distressed Denim Jacket
Saint Laurent Cropped Distressed Denim Jacket, $1,490, net-a-porter.com
![<p>Gianvito Rossi 100 Suede Pumps in Black, $670, <a href="http://www.net-a-porter.com/product/535955/Gianvito_Rossi/100-suede-pumps" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
6/34Gianvito Rossi 100 Suede Pumps in Black
Gianvito Rossi 100 Suede Pumps in Black, $670, net-a-porter.com
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![<p>Fendi Peekaboo Medium Leather Tote, $5,750, <a href="http://www.net-a-porter.com/product/504182/Fendi/peekaboo-medium-leather-tote" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
7/34Fendi Peekaboo Medium Leather Tote
Fendi Peekaboo Medium Leather Tote, $5,750, net-a-porter.com
![<p>You need to show your style, and still blend in with the Brooks Brothers briefcase set — Because if there’s one place that frowns upon a fashion risk, it’s a court of law.</p>]()
8/34Corporate Lawyer: The Challenge
You need to show your style, and still blend in with the Brooks Brothers briefcase set — Because if there’s one place that frowns upon a fashion risk, it’s a court of law.
![<p>An unstructured, obi-belted blazer gives your look a low-key update — just make sure the rest of your outfit is as traditional as a trial brief.</p>]()
9/34Corporate Lawyer: The Solution
An unstructured, obi-belted blazer gives your look a low-key update — just make sure the rest of your outfit is as traditional as a trial brief.
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![<p>The Row Haki Satin-Twill Wrap Top, $2,190, <a href="http://www.net-a-porter.com/us/en/product/602824" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
10/34The Row Haki Satin-Twill Wrap Top
The Row Haki Satin-Twill Wrap Top, $2,190, net-a-porter.com
![<p>Bottega Veneta Wool-Piqué Straight-Leg Pants, $850, <a href="http://www.net-a-porter.com/us/en/product/604339" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
11/34Bottega Veneta Wool-Piqué Straight-Leg Pants
Bottega Veneta Wool-Piqué Straight-Leg Pants, $850, net-a-porter.com
![<p>Balenciaga Oversized Wool-Blend Coat, $2,815, <a href="http://www.net-a-porter.com/us/en/product/618770" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
12/34Balenciaga Oversized Wool-Blend Coat
Balenciaga Oversized Wool-Blend Coat, $2,815, net-a-porter.com
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![<p>Jimmy Choo Black Suede Anouk Pointy Toe Pumps, $595, <a href="http://us.jimmychoo.com/en/women/shoes/pumps/anouk/black-suede-pointy-toe-pumps-ANOUKSUE001.html?cgid=women-shoes-pumps#prefn1=color&prefn2=heelHeight&psortd1=1&psortb1=bestMatch&prefv1=Black&prefv2=High+Heel&productsearch=true&start=1" rel="nofollow noopener" target="_blank" data-ylk="slk:jimmychoo.com;elm:context_link;itc:0" class="link ">jimmychoo.com</a></p>]()
13/34Jimmy Choo Black Suede Anouk Pointy Toe Pumps
Jimmy Choo Black Suede Anouk Pointy Toe Pumps, $595, jimmychoo.com
![<p>Sure, you had to read “<a href="http://www.amazon.com/John-Molloys-New-Dress-Success/dp/0446385522" rel="nofollow noopener" target="_blank" data-ylk="slk:Dress For Success;elm:context_link;itc:0" class="link ">Dress For Success</a>” for your MBA coursework — but you don’t <i>really</i> have to sell out and buy a power suit…right?</p>]()
14/34Office Manager: The Challenge
Sure, you had to read “Dress For Success” for your MBA coursework — but you don’t really have to sell out and buy a power suit…right?
![<p>Think in terms of understated updates to suiting basics. A row of pleats at the neck gives the crisp cotton shirt a whole new appeal, while an elongated take on the gray blazer is a look so conservative, it’s cool.</p>]()
15/34Office Manager: The Solution
Think in terms of understated updates to suiting basics. A row of pleats at the neck gives the crisp cotton shirt a whole new appeal, while an elongated take on the gray blazer is a look so conservative, it’s cool.
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![<p>NO.21 Ruffle-Trimmed Cotton-Poplin Shirt, $720, <a href="http://www.net-a-porter.com/us/en/product/611070" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
16/34NO.21 Ruffle-Trimmed Cotton-Poplin Shirt
NO.21 Ruffle-Trimmed Cotton-Poplin Shirt, $720, net-a-porter.com
![<p>Michael Kors Collection Mélange Wool and Cashmere-Blend Wide-Leg Pants, $1,194, <a href="http://www.net-a-porter.com/us/en/product/602447" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
17/34Michael Kors Collection Mélange Wool and Cashmere-Blend Wide-Leg Pants
Michael Kors Collection Mélange Wool and Cashmere-Blend Wide-Leg Pants, $1,194, net-a-porter.com
![<p>Protagonist Double-Breasted Stretch-Wool Coat, $1,620, <a href="http://www.net-a-porter.com/us/en/product/604842" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
18/34Protagonist Double-Breasted Stretch-Wool Coat
Protagonist Double-Breasted Stretch-Wool Coat, $1,620, net-a-porter.com
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![<p>Gucci Horsebit-Detailed Leather Loafers, $695, <a href="http://www.net-a-porter.com/product/607331/Gucci/horsebit-detailed-leather-loafers" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
19/34Gucci Horsebit-Detailed Leather Loafers
Gucci Horsebit-Detailed Leather Loafers, $695, net-a-porter.com
![<p>Le Specs Drop Top Aviator-Style Gold-Tone Mirrored Sunglasses, $80, <a href="http://www.net-a-porter.com/us/en/product/636210" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
20/34Le Specs Drop Top Aviator-Style Gold-Tone Mirrored Sunglasses
Le Specs Drop Top Aviator-Style Gold-Tone Mirrored Sunglasses, $80, net-a-porter.com
![<p>Congrats: You’re your own boss, and you work from home (you’re basically living the dream). Your challenge is to stay comfy, yet presentable — because you never know when your first big advertiser (or Anna Wintour) could come calling.</p>]()
21/34Freelance Writer: The Challenge
Congrats: You’re your own boss, and you work from home (you’re basically living the dream). Your challenge is to stay comfy, yet presentable — because you never know when your first big advertiser (or Anna Wintour) could come calling.
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![<p>An oversized shirt and truly comfy pant that go from “PJ-like” to “presentable” in an instant.</p>]()
22/34Freelance Writer: The Solution
An oversized shirt and truly comfy pant that go from “PJ-like” to “presentable” in an instant.
![<p>J. Crew Patchwork Cargo Pant, $148, <a href="https://www.jcrew.com/womens_category/pants/Straight/PRDOVR~E3121/E3121.jsp" rel="nofollow noopener" target="_blank" data-ylk="slk:jcrew.com;elm:context_link;itc:0" class="link ">jcrew.com</a></p>]()
23/34J. Crew Patchwork Cargo Pant
J. Crew Patchwork Cargo Pant, $148, jcrew.com
![<p>Victoria Beckham Denim Oversized Striped Cotton-Poplin Shirt, $450, <a href="http://www.net-a-porter.com/us/en/product/609234" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
24/34Victoria Beckham Denim Oversized Striped Cotton-Poplin Shirt
Victoria Beckham Denim Oversized Striped Cotton-Poplin Shirt, $450, net-a-porter.com
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![<p>Saint Laurent Wool-Gabardine Blazer, $3,390, <a href="http://www.net-a-porter.com/us/en/product/592449" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
25/34Saint Laurent Wool-Gabardine Blazer
Saint Laurent Wool-Gabardine Blazer, $3,390, net-a-porter.com
![<p>Gianvito Rossi 100 Suede Pumps, $670, <a href="http://www.net-a-porter.com/product/535956" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
26/34Gianvito Rossi 100 Suede Pumps
Gianvito Rossi 100 Suede Pumps, $670, net-a-porter.com
![<p>Loewe Large Suede Clutch, $650, <a href="http://www.net-a-porter.com/us/en/product/594288" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
27/34Loewe Large Suede Clutch
Loewe Large Suede Clutch, $650, net-a-porter.com
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![<p>Yes, you can be a school administrator without consigning yourself to a lifetime of shapeless skirt-suits. Because, contrary to popular belief, they do not confiscate your style cred when they hand out your teaching cert.</p>]()
28/34School Principal: The Challenge
Yes, you can be a school administrator without consigning yourself to a lifetime of shapeless skirt-suits. Because, contrary to popular belief, they do not confiscate your style cred when they hand out your teaching cert.
![<p>This season’s ‘70s obsession has a distinctly back-to-school vibe. A knee-length skirt tones down the sexiness of knee-high boots, while a silk blouse and structured bag are always appropriate. And voilà — a look that’s not too “Hot For Teacher,” nor Mrs. Norbury from <i>Mean Girls</i> (and that’s a good thing).</p>]()
29/34School Principal: The Solution
This season’s ‘70s obsession has a distinctly back-to-school vibe. A knee-length skirt tones down the sexiness of knee-high boots, while a silk blouse and structured bag are always appropriate. And voilà — a look that’s not too “Hot For Teacher,” nor Mrs. Norbury from Mean Girls (and that’s a good thing).
![<p>Jason Wu Wool Wrap Skirt, $1,195, <a href="http://www.net-a-porter.com/us/en/product/596950" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
30/34Jason Wu Wool Wrap Skirt
Jason Wu Wool Wrap Skirt, $1,195, net-a-porter.com
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![<p>Frame Denim Le Classic Striped Washed Silk-Carmeuse Shirt, $240, <a href="http://www.net-a-porter.com/us/en/product/609708" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
31/34Frame Denim Le Classic Striped Washed Silk-Carmeuse Shirt
Frame Denim Le Classic Striped Washed Silk-Carmeuse Shirt, $240, net-a-porter.com
![<p>Proenza Schouler Leather Knee Boots, $1,395, <a href="http://www.net-a-porter.com/us/en/product/570557" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
32/34Proenza Schouler Leather Knee Boots
Proenza Schouler Leather Knee Boots, $1,395, net-a-porter.com
![<p>Chloé Faye Python Shoulder Bag, $3,800, <a href="http://www.net-a-porter.com/product/587199/Chloe/faye-python-shoulder-bag" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
33/34Chloé Faye Python Shoulder Bag
Chloé Faye Python Shoulder Bag, $3,800, net-a-porter.com
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![<p>Linda Farrow Cat Eye Acetate Optical Glasses, $600, <a href="http://www.net-a-porter.com/us/en/product/530610" rel="nofollow noopener" target="_blank" data-ylk="slk:net-a-porter.com;elm:context_link;itc:0" class="link ">net-a-porter.com</a></p>]()
34/34Linda Farrow Cat Eye Acetate Optical Glasses
Linda Farrow Cat Eye Acetate Optical Glasses, $600, net-a-porter.com
Getting dressed for work in the morning is never an easy feat — and that goes double when you’re the boss. The right outfit needs to command respect, communicate your style, and with any luck, subtly let people know you’re the kind of has-it-all-together #GirlBoss they should be listening to.
Whether you’re climbing the corporate ladder, in the trenches of academia, or building a blogging empire from your living room couch, we’ve identified five common OOTD challenges — and we’ll show you how a boss solves ‘em all, straight ahead.
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