Your mama always told you never to wear black with brown or white after Labor Day—but fashion rules are meant to be broken, right?
We’re giving you permission to break all 50 of these old school rules.
50. Red and pink clash
Somewhere along the way, these two shades got a bad reputation, but when paired purposefully, they can actually look quite modern and eye-catching. To break this fashion rule, keep the red true, and add any shade of pink, from pastel to fuchsia.
49. Don’t wear white after labor day
Lame! As countless designers have proved during the past few seasons, white isn’t only appropriate when the weather gets cold, but also amazingly fresh and modern-feeling. One thing to keep in mind when tackling the white-in-winter trend: It’s all about the fabric. Lighter textiles such as white cotton, linen, canvas, and seersucker will surely look out of place during the chilly months of fall and winter, so be sure you’re reaching for white wool, cashmere, mohair, flannel, silk, and leather.
48. Don’t wear white shoes after labor day
Another fashion rule to break, as several “It” designers including Céline, Mulberry, Pringle of Scotland consistently showcase white boots, loafers, and flats in winter-white leather and suede. Even fast-fashion spots like Zara are starting to roll out white boots for fall, so get on it!
47. Take off one accessory before leaving the house
Why? As fabulous women like Iris Apfel have proven time and time again, piling on the bling can be fabulous and totally idiosyncratic.
46. Navy and black don’t go together
This fashion rule still has its fair share of subscribers, but let us make it clear: Navy and black look super-chic together. The combo first started making waves during the Fall 2012 collections, as scores of designers including Carolina Herrera, Miu Miu, Gucci, Prabal Gurung and Céline incorporated black and navy into runway looks,while It-gals like Alexa Chung, and Mary-Kate and Ashley Olsen were quick to team up the hues. Even if it’s only adding a pair of opaque black tights to a navy blue dress, it’s a rule worth breaking.
45. Shorts are only for summer
False. There’s something incredibly cool and fuss-free about rocking a pair of shorts in the winter paired with opaque black tights and ankle booties. Stay away from shorts in summery fabrics like eyelet and cotton, but go ahead and rock shorts made from leather, wool, jacquard, even denim cutoffs, which look super-cool paired with ankle boots, tights, and a chunky sweater come fall and winter.
44. Mixed prints are too busy
Actually, mixed prints can look extremely fresh, and elevate your look from ordinary to street-style ready in no time. Street style pros know that anything goes when it comes to melding motifs (florals with stripes! polka dots with Ikat!), but beginners should start with this tip: Treating leopard like a neutral is the easiest way to break into pattern mixing. Whatever colored print you choose, add a leopard belt, shoe, bag, blouse, or anything else.
43. You have to wear silver or gold jewelry, not both
As we’ve seen on countless bloggers, street style stars, and celebrities, mixing metals when it comes to jewelry can look fresh and very now. The trick? Make it look deliberate as opposed to haphazard. The easiest way to do it is to up your arm-swag game by stacking bracelets in varying widths and shades of silver and gold. Same goes for rings: layer several in silver and gold that are both thick and thin. To really go for it, toss some rose gold in the mix, too.
42. Petite girls can’t wear maxi skirts
It’s common fashion folklore that small women simply can’t wear floor-grazing skirts and dresses, but luckily that’s been proven entirely false. In fact, a well-cut maxi skirt can actually give you the appearance of looking taller, as evidenced by petite gals like Rachel Bilson, Rachel Zoe, and Mary-Kate Olsen. Choose solid versions that skim the length of your body, which will create a long vertical line (forego anything with thick pleats or too many layers.) Be sure to keep your top fitted—a tucked-in T-shirt and a cropped leather jacket, for example—so as to not drown in fabric. Also, make sure the skirt’s hemline is as long as you can go without tripping, and add a pair of wedges or heels underneath.
41. Or midi skirts
Skirts that fall below the knee but above the ankle are often considered a don’t for women who aren’t long and lean, but if the proportions are right, they can add a striking, often retro appeal to any look. Midi skirts with a slight flare can be super-flattering on smaller girls, so long as they’re paired with a dainty pair of heels and tucked-in or slightly shrunken tops, so as not to get swallowed up in fabric.
40. Horizontal stripes make you look larger
Horizontal lines making you look wider is a pretty cliché “rule.” Yes, a skin-tight shiny Spandex bodycon dress emblazoned with horizontal lines might only look good on a model, but pieces that are made well and fit well—think a classic cotton Breton striped shirt tucked into dark jeans, or a ladylike full skirt with horizontal stripes—flatters every woman.
39. “Classics” have to cost a ton of money
Most women can’t or prefer not to drop a ton of cash on clothes every season, even on the staples we’re told will always be in style. That’s why off-price retailers such as TJ Maxx, Marshalls, and Century 21 are so great for scoring real designer pieces at a fraction of the cost. Even several fast-fashion stores like Zara and Uniqlo are upping their game and quality, offering an array of timelessly chic stylish pieces such as wool overcoats, leather Chelsea boots, wool and cashmere sweaters, and silk blouses at wallet-friendly prices.
38. You can’t wear red to a wedding
This somewhat ridiculous fashion rule was put into place during more conservative times when red was thought to be a way-too-sexy, attention-stealing color. Yes, you might want to stay away from wearing a skin-tight red plunging spandex gown to a wedding, but you probably don’t want to wear that in any color. These days, there are tons of high-style red dresses that look perfectly acceptable at weddings.
37. Faux fur and leather are tacky
Today, so many fashion-obsessed gals are also quite socially conscious, and retailers have taken notice. Whereas fake fur and leather were once cheap-looking and tawdry, many of today’s pieces look almost identical to the real thing.
36. Sneakers are only for the gym
As recent trends have proven, the right pair of sneakers can take you way beyond the gym. Between wedge sneakers, slip-on sneakers (a huge trend for fall), and the rise of top bloggers and fashion insiders rocking sporty Nikes, New Balance, and Adidas kicks with everything from sleek skirts to leather pants, it’s clear that when styled with dressier pieces, sneakers can add a modern twist to an outfit that’s not comprised solely of sweats.
35. Every women must own a trench coat. Or ballet flats. Or a black shift dress.
Don’t those types of fashion rules feel wildly out of date these days? There’s no mandate that says every woman has to own (or even like) the “classic,” mostly conservative items that constantly show up on fashion insiders’ essentials lists. Ballet flats not your thing? Break the “rule” and wear the flats you like instead.
34. You need shampoo to wash your hair
As curly girls well know, shampoo can actually strip thick and spirally hair of necessary oils, and be way too harsh for delicate hair. Oftentimes, water and the right conditioner is enough, but if you feel you have excessive product buildup, try using a little apple cider vinegar beforehand.
33. “Dry clean only” tags are always correct
If a garment says it needs to be dry-cleaned, it won’t hurt to follow suit, but that can get pricey—especially since some items technically don’t need to be professionally cleaned. Many high-end brands that manufacture items in washable fabrics will often say “dry clean only” to keep up the higher-end vibe. Furthermore, certain fabrics such as cashmere actually hold up better when they’re washed by hand as opposed to getting dry-cleaned.
32. Dresses and pants don’t mix
While you might not wear a gown over a pair of trousers, there’s something very modern about pairing a swingy mini-dress with skinny jeans, or a flowing chiffon midi dress with leather leggings, a look we’ve been seeing on runways and on street style stars lately.
31. Denim on denim is a fashion faux pas
Also known as a Canadian tuxedo, the easiest trick to rocking double denim without looking like you got lost on the way to the cattle ranch: Pair pieces of varying washes together, such as a light denim shirt with dark denim jeans, or a dark denim jacket with a light-wash pair of denim shorts.
29. You should always match your shoes, bag, and belt
That might have true in your grandma’s day, but it’s total a non-issue in this day and age. In fact, matching all your accessories perfectly can make you look dated and matronly, whereas mixing things up looks fresh and modern, and adds interest to an outfit.
28. Red lipstick is only for evening
At one time, bold beauty choices—a scarlet lip or a smoky eye, for example—were considered way too “evening” for daylight, but a bright red lip (or orange, pink, or deep plum) can act as its own accessory and liven up any daytime look. If you do go with a statement-making lip or eye while the sun’s out, be sure to keep the rest of your makeup minimal, and your outfit polished.
27. Tall women shouldn’t wear heels
This mandate isn’t only silly, but a little sexist, too. Stemming from a whole bunch of antiquated notions including abundant height isn’t feminine, and a woman shouldn’t draw extra attention to herself, this rule is one no woman should ever follow if they don’t want to. We know plenty of women who are almost six feet tall and still rock three-inch heels with grace (and we’re jealous).
26. Sweatpants can never be worn outside the house
As recent sportif trends have showcased, a well-fitting pair of sweatpants can actually look very cool when paired with things like peep-toe booties or heels, and a structured blazer. See how here.
25. Only wear one bold color at a time
If we’ve learned anything from the recent color-blocking phenom, it’s that a bold saturated hue can look even better when paired with another bold saturated hue. Wearing an emerald green silk blouse? Don’t be afraid to wear those fuchsia suede heels or carry that sunny yellow leather clutch—you’ll look super-modern and striking.
24. Pastels are only for Easter or for springtime
23. Once a garment is ironed, it won’t wrinkle
Actually, you should never put a garment on immediately after ironing, as this can actually cause new wrinkles to form. Instead, let it sit for five minutes to set the press.
22. Sunglasses have to be neutral
Black and tortoise frames will forever be in style, but lately, trend-setting designers such as Karen Walker and Stella McCartney, as well as fashion-forward gals have ditched the super-dark frames in favor of cool pastel styles. The shapes are varied—classic wayfarer, round, cat-eye, square, hexagonal—and the shades are sweet (tangerine, mint, pink, lavender) or bold (red, yellow, or print.)
21. Actual menswear is just for men
Obviously, you’re not going to pick up a suit at Rochester Big and Tall, but you’d be surprised by how many made-for-men pieces can work for you. This is especially true at common outposts like Forever 21, H&M, J. Crew, and Zara, whose men’s stuff—think slim-cut button-downs, sweatshirts, sweaters, and utility jackets—often aren’t as trendy as their for-women counterparts, and offer a slightly slouchier fit.
20. Glitzy fabrics like sequins can’t be worn during the day
A modern trick to looking like the most effortlessly stylish girl on the street: Pair dressy bottoms like a beaded skirt, or sequin pants) with casual staples like a white shirt, a gray crew-neck sweatshirt, or a black blazer.
19. Sweatshirts are strictly casual wear
Once strictly for athletes, gym-goers, and errand-runners, the humble sweatshirt has risen to become such a very stylish staple. Need proof? Top designers like Kenzo, Phillip Lim, Cynthia Rowley, and Karen Walker have been showcasing versions that are embellished and printed, while street style stars starting pairing their sweatshirts with swingy skirts, skinny trousers, and statement necklaces.
18. Clear heels are for strippers
Lucite heels have a bad reputation for being common stripper fare, but several designers have embraced the clear heel mentality to create interesting shoes. The trick to look chic, not cheap? Make sure the heels are thick and boxy (or a wedge, like Maison Martin Margiela x H&M’s notable lucite wedges) and there’s no platform.
17. Always buy the same size in clothes
As any woman who’s shopped high-fashion and fast-fashion knows, sizing can vary tremendously according to store, brand, and item. Cheaper clothing typically runs way bigger, making it common for a woman to wear, say, a size large pants at Forever 21, but still be a size 2 in Stella McCartney. Don’t sweat the number, but rather pay attention to how things look on your body.
16. Clutches are only for nighttime
It seems the after-hours staple is fast moving into daylight, as we’ve been spotting countless influencers using small strap-free bags during the day at Fashion Week, on various style blogs, and right here in New York City on any given day. While some are fairly casual, like oversized leather clutches, others are dressy (i.e., shiny gold clutches and beaded clutch bags), and all look fabulous with things like faded jeans.
15. No short skirts after 40
To be honest, we find the idea of age-appropriate dressing quite boring. Indeed, we agree that most women past the age of 16 probably shouldn’t wear certain things (One Direction T-Shirts, for example), but to tell a women she shouldn’t wear a miniskirt because she’s over 40 is ludicrous. Just make sure the skirt is paired with chic staples (and tights in the winter). Check out how good 42-year-old Sofia Coppola looks!
14. Brown and black don’t mix
This has long been a fashion rule that’s made to be broken, as black and brown actually go together quite well. For example, how chic does it look when you wear black jeans, a black overcoat, and your trusty brown Chelsea boots? Or a brown leather skirt with a black turtleneck and black tights?
13. Faux diamonds are a fashion faux pas
While fake designer bags are a huge don’t, fake diamond studs in a reasonable size are a huge do. Why? Because faux stones are hard to spot to the untrained eye.
12. An old coat is a lost cause
If you have an overcoat whose details are starting to look dated, a good tailor can completely change the length, swap out the buttons for something more modern, replace the lining with something eye-catching, like a pattern or a bright color, and sew on additions like a vintage fur collar.
11. Keep your shoes in shoeboxes
Most closet experts will say the opposite: Line shoes up on the floor of your closet, or on shelves if you have room. This takes up less space and ensures you’re always aware of what you have. If you’re anxious about protecting them, invest in dust bags.
10. Don’t wear socks and sandals
This is probably one of the biggest fashion rules out there, but lately it’s being broken left and right by the style set, who rock socks and sandals with everything from jeans to swingy skirts. Sandals and tights also work!
9. Jewelry boxes are best for storing your all your jewelry
The best way to store fashion jewelry, including Sterling Silver, is in Ziploc bags. This helps pieces retain luster and reduces tarnishing and scratches.
8. A shower is the only way to get rid of too much perfume
If you spritz too much perfume on yourself, use unscented, oil-based makeup remover to remove excess perfume. Your co-workers will thank you!
7. Loose styles flatter plus-size women most
It’s a myth that loose, flowy styles flatter a large bust or a plus-size woman. The area just under the bust is a woman’s smallest torso measurement, so emphasizing it with a structured waistband that hits higher than your natural waist will make you look a size smaller.
6. Jeans should be washed as much as your other clothing
Denim aficionados know that raw denim can take up to six months to break in and shouldn’t be washed until then. Why? Jeans really do conform to our bodies, and when you wash them, most of the shape is lost. Most jeans today, however, are treated (pre-washed to achieve a faded look) and don’t need to be broken in. These you can wash more often, but only when they’re stained or when they start to sag. To zap odors, hang them in the bathroom while you’re showering or freeze them in a plastic bag for a day or two.
5. Overalls can’t ever be chic
We’ve seen this rule continually be broken by models, bloggers, and street style stars who regularly step out in slim-fitting denim overalls, or versions in modern fabrics like leather or silk, and pairing them with sleek staples like blouses, wool overcoats, and classic pumps.
4. Sheer tops can’t be worn to work
The sheer trend has been gaining steam during the past few seasons, and while we wouldn’t suggest wearing a see-through blouse with nothing underneath but a bra to the office, pairing that blouse with a silk camisole at work is perfectly appropriate. Own a sheer T-shirt? Try layering it over a solid button-down for a very Céline-y styling trick.
3. Only dry clean your clothes after storing them, not before
False! If you’re storing clothes in a storage unit, basement, or attic it’s imperative to get the garments dry cleaned first, as moths and other pests are attracted to our everyday scents like perfume, food, deodorant, and smoke. Same goes for bags: Empty the contents before storing, as crumbs can attract bugs, pens can leak, and lipsticks can melt. Ew!
2. High-waist pants are always unflattering
High-waist bottoms get a bad rap (probably thanks to an unfortunate Jessica Simpson style mishap)—but when worn correctly, they can trick the eye into thinking you’re taller and leaner by elongating your lower body. The most slimming item to choose are slightly high-rise slim-fitting jeans that hit your ankle, or simple high-black black trousers.
1. Fashion rules are meant to be followed and taken seriously
As you can see, they’re not. Wear what makes you feel awesome!
Originally published November 2013. Updated March 2017.