10 Timeless Looks That Will Never Go out of Style

10 Timeless Looks

As I get a little bit older, I am less impressed by trends or wooed by any and every cheap buy that hangs on the sale rack. Don’t get me wrong, I am still a gal on a hunt for the best deal, but let’s just say that these days I find that I am looking for the best deals for the best things. Instead of quantity I am trying to opt for quality. After a major overhaul on my closet this new year, I have vowed to really think twice about what I will spend our hard-earned money on and bring into my closet and life. My first rule: I have to LOVE it — I mean really, really love it. On a scale from 1 to 10, it needs to be a 1o or at least a 9.5. Secondly, or a close tie to one, it has to FIT just right. Gone are the clothes that are a tad too big or a tad too small. Having the right fit means I can breath, chase after my toddler, and keep the necessaries covered, while also flattering my frame without a bunch of extra stuff, layers, belts, pins, tugging, or pulling. So as it turns out, I have also come to find that the clothing that tends to fit those 2 criteria are classic, timeless pieces that are well-made, simple, and versatile. Coincidence? Not likely…

Of course you can still get some great things for great deals, however there are some items that are investment pieces, even at deal prices. Remember, an investment stays with you over time and proves its worth. These pieces have all proved to be worthy investments, tried and true. These are the work horses of my wardrobe and are the basis of most of my day-to-day looks.

Also it should be said that “classic” can sometimes be misinterpreted as “basic” or “boring.” However, I beg to differ. While they remain steadfast in simplicity, they offer the perfect canvas to embellish and play upon. You can always mix things up with current trends, bright colors, and interesting accessories. And yet, at the end of the day, just these looks alone stand on their own two feet with an air of effortlessness.

So with out further ado, may I present to you 10 timeless looks that will never go out of style…

  • Dark Blue 1 of 10
    Bootcut Dark Denim

    Nothing flatters the lower half of our frame like a pair of bootcut, dark denim jeans! Forget skinnys, boyfriends, distressed, light- wash or ankle-cut jeans, these are all trends that will come and go. Remember acid wash? Yeah I try not to. A deep dark shade of blue jean, however, is forever. If you are going to spend all your money on a pair of jeans, these will give you the most bang for your buck. Pair it with a crisp white T-shirt tucked in for a look that is as hip as it is timeless. On the days that you have "nothing to wear," this is your something to wear.


    Tip: Again, fit is everything! Depending on the brand, I like to buy my jeans a bit on the snug side, as most dark denim will stretch. For the most timeless look, go for a mid-rise that's not too high or too low, and then make sure that the length is just right to wear with a moderate heal for comfort, but for a long, lean-looking leg. If you can't find the perfect length, buy long and get them tailored! They should last you no less than a decade!


    Purchase Sexy Bootcut jeans from The Gap, $69.95

    Purchase white T-shirt from Target, $9

    Purchase similar hat from Stetson

    Purchase similar shoes from Nordstrom, $79.95

  • Pencil It In 2 of 10
    The Pencil Skirt

    Flattering, slimming, conservative, and classy ... yet sexy, this skirt means business in every sense of the word. You can wear the pencil skirt to the office, but mix up your top with a chambray or satiny sheen blouse for a night out. It's appropriate for church, or for the first lady. Everyone needs a pencil skirt; it's a staple.


    Tip: If you are on the hunt for a classic pencil skirt, watch that the waistband doesn't sit on or below the hips. The pencil skirt looks best when worn closer to the natural waistline and is tapered around the hip and down the leg accentuating your lady-like curves. It should fit well, but not be so snug that it starts to ride up. Keep it classy!


    Purchase similar skirt from Nordstrom, $68

    Purchase similar shirt from J.Crew, $78

  • Button-Down 3 of 10
    White Button Down

    Likely you have a white button-down in your closet, and if you don't, you need one — stat! The white button-down is one of the most versatile pieces a girl (or a guy for that matter) can own. Of course white has been a super hot trend for a while now, and we've all agreed to do away with that whole "no white after labor day rule" so it's acceptable to wear all-year-round. But the white collared shirt can hardly be called a trend because everyone has worn a button-down, from George Washington to J.Lo.


    Tip: The only downside to the white button down is the maintenance. Avoid yellow armpits and collars by getting them dry-cleaned or professionally laundered, and keep them hanging in the plastic.


    Purchase similar top from Anthro, $88

    Purchase similar belt from J.Crew, $48

    Purchase similar white jeans from Target, $22.99

    Purchase 31 Bits Bracelet from 31bits, $28


  • Leo Pump 4 of 10
    Leopard heels

    My inspiration for this look started with the leopard pump, however the whole ensemble is worth noting when it comes to classic and timeless style. Starting with the shoes, we have seen a huge trend towards all things leopard. While the pump has been around for ages, before they were only worn by the most daring of fashionistas. Now they've been deemed a neutral and a classic. The most conservative woman on the block can wear these shoes in a kitten heel and feel comfortable, while the risk-taker might take them in a 6-inch platform and it's just another day. Either way this print works for everyone in this small but noticeable statement. Then there is the black jean and the denim top. Put it all together and you don't need much more. This is one those outfits I travel with because it's easy and it works for just about any occasion give or take a few accessories. 


    Tip: When wearing leopard print, keep your eye out for smaller to medium prints as opposed to large leopard prints for a chicer and less brassy look. Also opt for a toe that isn't too pointy and yet isn't round. The slightly rounded point is the look to aim for, for longevity.


    Purchase similar shoes from Piperlime, $80

    Purchase similar black jeans from Old Navy, $25

    Purchase Levi Denim Shirt from Levi, $48

    Purchase watch from Feral Watches, $88

  • Little Black Dress 5 of 10
    Little Black Dress

    Obvious, I know, but no top 10 timeless looks post should be without the LBD. Because this dress will never, ever (yes in this case we can say never) go out of style, it wouldn't be a bad idea to invest in a high quality piece that fits you to a T. I found this clean tailored number at Banana Republic in a shape and hue that won't leave the racks for eons to come. 


    Tip: When buying a LBD, fit is number one! Second is simplicity of silhouette: the less frills and trendy details, the better. The more simple and chic, the longer wear you will get!


    Purchase Sloan Dress from Banana Republic, $140

    Purchase similar earrings from Nordstrom, $34

  • Jean Jackets 6 of 10
    The Jean Jacket

    You know those days that it's a little cool out and yet you don't want to mess up your outfit so you try on: a cardigan — too librarian; a leather jacket — to tough; a suit coat — too business; but then you try on the jean jacket and it's just — cool! Yes, the denim jacket makes most daytime looks just right, and instead of taking away from your outfit, it adds to it! 


    Tip: Just like your jeans, look for a classic wash. Darker is probably best, but a medium wash is also a safe bet. Stay away from cropped jackets; if you want to wear it for a long time, look for it to hit at the top of the hip. Also, it's always cool to roll up the cuffs a little bit. 


    Purchase this jacket from H&M, $39.95

    Purchase shirt from Cotton On, $5

    DIY this tassel necklace HERE

    Purchase similar shoes from Nordstrom, $128.95

  • Stripes and Cognac 7 of 10
    Stripes & Crossbody

    Stripes: What is it about them that makes us swoon and sigh? Is it their bold contrast, their straight lines, their simplicity? Whatever it is, it's here to stay through winter, spring, summer, or fall — and through the rest of time, for that matter. There isn't much more to say about them other than that they are my absolute favorite.  Then you have the small cross body bag in cognac, which is also my favorite, or at least a close-second. I gave up on big heavy bags that I had to hold; I don't have the energy anymore to hold such things, especially now that I have a walking, talking, running, climbing, screaming toddler. Hands free is best if you ask me, and in none other than cognac. This color just looks beautiful with almost everything. I have been wearing this purse for two years, you can still buy it today.


    Tip: People say to stay away from horizontal stripes, but don't listen because vertical stripes make you look like you're a ref. I just say wear stripes — lots of them. As for the purse, look for some decent inner compartments; the bag should still be functional!


    Purchase similar shirt from Gap, $26.95

    Purchase Marc Jacobs bag from Nordstrom, $198

    Purchase Begley Glasses from Warby Parker, $95

  • Wrap It Up 8 of 10
    The Wrap Dress

    Diane von Furstenburg put the wrap dress on the map back in the '70s, and it's been going strong ever since. This style of a dress will always be available and will always flatter a woman's body. Let me tell you why: The "wrap" is wrapped around the smallest part of the waist and can always be adjusted to the exact size necessary. Also, the wrap creates a V-neck line, elongating the neck and flattering the chest — even the smallest, and then because the length is rarely too short — keeping the hem around the knee, it makes the dress practical and easy to move in. I rest my case. Diane isn't the only designer to come out with the wrap dress, as everyone these days has their own version at any price point imaginable. Lastly, the wrap dress isn't just timeless, it's ageless — from 22 to 52 — this look makes the most of whatever a girl's got, no matter how old or young she is.


    Tip: Buy a wrap dress 🙂


    Purchase similar dress from Banana Republic, $98

    Purchase similar shoes from Nordstrom, $73.66

  • In the Trench 9 of 10
    Tench Coat

    It might be spring, but before we get to May flowers, we have to get through April showers. And in some places, April snow storms, so we might still need a bit of warmth till the sun comes out to stay. The khaki trench coat is the perfect choice! Much like the wrap dress, the waist belt makes this coat flattering, and the length keeps your bum warm and covered. Also, as made use of in the picture above, the trench has perfectly placed pockets! I am a girl that loves pockets! Lastly, the color is so neutral that it usually does just the right trick for any look.


    Tip: Trench coats come in nearly every length and weigh. Depending on the climate you live in, opt for a longer or shorter, heavier or lighter, coat. For spring on the west coast, this length and weight is just right.


    Purchase similar jacket from H&M, $49.95

    Purchase similar shoes from Nordstrom, $128

    Purchase similar jeans from Nordstrom, $165

  • Blaze On 10 of 10
    The Blazer

    The black blazer ... what can I say. Another silhouette that just does great things for the upper body. I love the way a well-suited blazer defines the shoulders with clean crisp lines. I love the way it drapes, slimming the waist and skimming over the hips. It is elegant, it is rockstar, it is business, it is casual. What can't it do? 


    Tip: I know I sound redundant, but it's all about the FIT FIT FIT! Steer clear of boxy cuts and oversized fits. Sure these might fit the trend, but for it to fit forever, opt for a more trim, tailored look. Rolling up the sleeves keeps it fresh. This is an investment piece, so save your money and buy a quality blazer that can stand the test of time. 


    Purchase similar Smythe jacket from Neiman Marcus, $173 

    Purchase jeans from Gap, $69.95

    Purchase similar hat from Nordstrom, $46 

Photos by Priscilla Chang

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Article Posted 3 years Ago

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