The 10 Wardrobe Essentials I Happily Buy Over and Over Again

Last month, I wrote about the fashion classics everyone says I should buy but don’t. Today I’m flipping the script and talking about the clothes I couldn’t live without. The ones I wear over and over again and constantly re-buy, because they always seem to suit me.

There are very few “shoulds” when it comes to personal style, but I do believe that everyone should always be dressing based off of their own lifestyle. That means that no two people’s classics are ever going to be the same. For example, I live in a big city where there are four seasons, and I work in a casual environment. So, a black pencil skirt? That has no place in my closet. But it might for someone else.

Without further ado, here are my 10 wardrobe must-have’s. It was hard to narrow down, but all of these are versatile pieces that mix and match with several other items in my wardrobe, and I’ve included my picks in a range of price points.

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1. Macintosh (Mac) Coat

The macintosh was invented as a rain jacket, but I wear mine about three months of the year, rain or shine, as long as it’s a little brisk outside. I can throw it on over a T-shirt and jeans and all of a sudden my look goes from sloppy to presentable. Needless to say, I’d feel like a lost puppy without one. I’ve had my current one for three years now, and will most likely re-buy a similar version once it goes kaput. Brown is a classic color, but also shows dirt more easily. Black can be a little severe. So navy is just right.

Trench coats have a similar purpose, but I prefer a cleaner, relaxed fit, so the traditional, double-breasted Burberry coats don’t appeal to me. And for a decidedly non-Inspector Gadget feel, I always go for macs instead of trenches.

Because I wear them a lot, I’m willing to spend more to get the exact look I want, but if you’re on a budget, remember that macs and trench coats are usually made out of cotton–you don’t need to go super high-end to still look put together. But watch out for fabrics that wrinkle easily.

Splurge: Cabourg Cotton Mac, A.P.C., $590
Mid-Range/Budget: The Mac Coat, Everlane, $125

2. Silk Button-Down

My work dress code is casual, but if there’s a holiday lunch or a birthday party that’s not at a dive bar, I need to step it up a bit. For someone like me who doesn’t wear dresses much, silk button-downs are a happy medium for looking appropriate for the occasion and still feeling like myself.

You don’t even have to buy silk if you don’t want to. There are plenty of ‘silky feel’ options that are less expensive, but still achieve a similar look.

Splurge: The Slim Signature, Equipment, $230
Mid-Range: Silk Button-Up Shirt, J. Crew, $120
Budget: Silk Shirt, Joe Fresh, $59

3. Leather Handbag

First, can I just say how hard it is to find leather bags that are budget-friendly? Leather is expensive, people! I also noticed that the cheaper bags tend to be over-designed and have a lot of embellishments. Surely this is a tactic to distract from the low quality of the bag.

I usually carry a lunch and sometimes a laptop around for work, so a leather tote is a must. With the simple shape, totes are one of the few bag styles that are timeless.

If you decide to splurge, the key is to avoid buying one that’s a total “It” bag, because it’s probably going to go out of style soon. If you like a bag, I’d wait a year or so to make sure it’s not a fleeting desire.

Splurge: Small Cabas Phantom Bag, Celine, $1,525
Mid-Range: Various, Lotuff, $690-$990
Budget: Day Market Tote, Everlane, $175

4. Printed Sweater

Most of my clothes are solid colors and very plain. To make things a little more fun, I gotta have a printed sweater. I have four and counting, so they’re now my signature. My sweaters also have to have a relaxed, boxier fit–no tight ones.

Even in the budget range, look for one that’s made out of natural materials, 100% cotton or wool. They’re harder to find, but they exist.

PS: The sweater in the picture is from Margaret Howell, and I can’t wait to visit her store when I am in the UK next summer.

Splurge: Diamond Fairisle Jumper, Margaret Howell, $365
Mid-Range: Heritage Merino Wool Sweater, Pendleton, $153
Budget: Classic Ragg Wool Sweater, L.L. Bean, $80

5. Unstructured, Slightly Oversized Blazer

I have two Theory blazers–one fitted suit-style one, and one oversized one. I never wear the fitted one, but I always reach for the oversized one. The reason? Because it’s about 1000% cooler. Similar to the mac coat, you can throw it on over anything and instantly look more polished.

You don’t want to compromise on fit here, so I’d recommend trying these on in person. If you find one that fits OK, but not great, move on.

Splurge: Grinson Blazer, Theory, $475
Mid-Range: Double-Breasted Blazer in Japanese Weave, J. Crew, $198
Budget: Ruched Sleeve Boyfriend Blazer, Express, $65

6. Boy-Fit T-Shirts

I will spend months looking for the perfect T-shirt. That’s because they’re my bread and butter, especially for summer. Once I find one I like, I’ll just re-buy the same one over and over. Colors that I will wear are white, grey and army green or khaki. I bought a black T-shirt once, but I never wore it, so now I know never to do that again.

Splurge: The Crewneck Tee, Rag & Bone, $85
Mid-Range: Classic T-Shirt, COS, $35
Budget: The Cotton Crew, Everlane, $16

7. 100% Cotton Straight-Cut Jeans

Along with T-shirts, I wear jeans almost every day, so I’m very specific about fabric and fit. I like denim to feel like real denim, even though ones with spandex are “more flattering.” From a fashion purist standpoint, I value 100% cotton denim much more than fabric blends, because it’s rare and old school. I will be the first to admit that raw A.P.C. jeans are not for everybody, but I feel like they were made for my exact build.

Splurge: Petit New Standard, A.P.C. $210
Mid-Range: 501 Skinny Jeans, Levi’s, $98
Budget: Sayana Organic Cotton Straight Jeans, Mango, $42

8. Versatile Printed Dress

I’ve mentioned that I’m not a dress person, but there are some times where you just can’t get around them. Think daytime weddings, job interviews, summer graduations, etc. I like the idea of just ONE dress that can work for a variety of occasions, and I think a printed silk version fits the bill. With the right accessories and shoes, you can make the one dress work for almost any event.

Splurge: Von Quincy Hunter Silk Dress, Diane Von Furstenberg, $468
Mid-Range: Printed Crossed Dress, Zara, $99.90
Budget: Midi Shirt Dress, Target, $37.99

9. Leather Sneakers

If we ever meet in person, one thing you’ll notice about me is I walk crazy fast. So, to maintain that compulsion, I need my shoes to keep me moving. Plus, I’ve been wearing sneakers since I was in middle school, so this isn’t just a fad for me. For that reason, a sneaker is an essential in my closet. I like “grown-up” versions in nicer materials–ones you could wear with a pair of work dress pants. Again, like denim and T-shirts, I wear these almost every day, so I justify spending whatever I need to to get exactly what I want.

Splurge: Achilles Low Sneakers, Common Projects, $375
Mid-Range: New Bold Sneakers, Adidas, $145
Budget: Kickstart Leather Sneakers, Keds, $40

10. Mid-Rise Denim Shorts

Summer is my least favorite season for fashion. I don’t wear dresses much, but I find myself always reaching for the same pair of denim shorts when it’s hot. They’re just so easy. I don’t worry about them getting wrinkled or being too delicate or washing them a specific way. They’re the trusty, durable standby that I can always rely on.