Workhorses vs. Show Ponies

Here to prove your wardrobe can be both.

Today’s newsletter is underwritten by Tory Burch, a 5 Things favorite. Thank you Tory Burch for continuing to believe in this letter and community!

A slew of prize winning workhorses! Keep scrolling…

I often hear from clients that they hesitate on color or print because they “don’t want to hate it in a month.” That is a fair concern! But without a little bit of flavor in the closet we run the risk of becoming walking, beige Pinterest boards. So today we are going to discuss picking pieces that add a little bit of extra but not so much so that you feel the need to sell, search and repeat the process of adding personal style in eight weeks. Pieces you can really wear and wear and wear again.

Let’s start this week with a few questions you can ask yourself when trying to determine of said addition fits the bill. Here are some I like to think about, though you might want to add one or two of your own:

• Is it a shape you/I feel confident in? I ask this in this way, because some people prefer to have more fitted options at work, and some prefer a more oversized fit. Neither is absolutely correct, it is personal preference. But can you put it on and immediately feel like yourself? If yes —>

• Does the color/texture/detail/cut add something that was not there before? If yes —>

• Can you spend 15 minutes in your closet trying to make five different outfits with it? If yes —>

• Would you feel good having a conversation with your boss or career role model in it? If yes —> YES!

Now, this doesn’t mean you will never be fatigued of these pieces with a little extra moxie. I keep on hand a single storage bin (I limit it to ONE as to not let my storage rates get out of control! :) ) of otherwise-in-season pieces that I love but need to give my eyes a rest from. Sometimes it not that you are totally over something but you just need a little break. This will allow you to really wear your pieces when they are IN the rotation, and avoid the decision fatigue and overwhelm of a packed closet.

Last week Erika Veurink, in her newsletter “Long Live”, wrote about how in the 1930s the average American woman owned nine outfits (it’s a great read!) and it got me thinking…I know we all say we are fine repeating outfits and really wearing our clothes, but there is still a bit of stigma around the concept when put into practice. Especially when we are talking about something as bold as a green skirt (see below!). If we could get over that mental hurdle, we would need so much less and could have so much more fun with the stuff we buy and love. So today is not only a look at some outfit ideas that you can save and refer back to when in a office styling rut, but also an invitation to spend some mental time with your special pieces to figure out how to wear them more.

You already know that I think the majority of our closets should serve a purpose. It should be that we wear 80% of our clothes regularly, not the 20% that Veurink claims we keep in rotation. (Erika, where did you get these stats!? So intriguing!) I want even the fun stuff to be considered workhorses. So lets get to it!!

A Bright Skirt

Specifically, an interesting straight skirt in a vibrant texture or color. You know I’m a big believer in skirts instead of dresses. Mostly because I find them proportionally easier…my barely there torso is never quite suited to a dress. But a bold skirt also leaves more room for personal style (layering!) and more space to tone down. Maybe a bright green dress could feel like too much for you. But a skirt, anchored by black tights and a black blazer is just the right hit of color. Or maybe you don’t love the look of yellow near your face, but in a skirt, no problem! Next week we are going to be talking about this shape of skirt in particular in all its glory (so consider this skirt a sneak peek to a broader conversation on this topic.

We are starting with this skirt today, bc it’s my favorite of the bunch. This color! Jungle Green anyone? The fabric!! It’s an embossed satin but meant to look like ostrich. Wild!! The elastic waistband. The shape. It works in the most “dress code-y” of settings but is also a totally appropriate (and fun) choice for those who might not have to answer to anyone’s corporate codes, yet still have places to be. I’m looking at you art dealers. CMOs. Moms-in-chief!

Tory Burch’s embossed satin skirt with a navy silk button down, navy blazer, black tights and wild boots. But your knee high black boots will look great too, obviously. This silk blouse is an old Phoebe Philo Celine and the blazer Uniqlo+J, a collectors item at this point. But the idea here is just a matching shirt and blazer. You could do black on black (Maybe your tux blazer we discussed last week?) with this top? Or navy on navy. This navy JWAxUniqlo looks awesome! Though I might change out the buttons to (faux) tortoise. Or this one! With a classic silk shirt underneath. (I’d size up one size to make it hang a little slouchier.)

I’m officially in my vintage New York “sportswear” era. I want to dress like a lady who lunches all the time…but without the time for a ladies lunch. The Tory skirt with a St. John lace cardigan, Doen velvet ballet flats and a Lura handbag. I’m really just showing you here how great the green looks with tan/blush. You don’t need to always anchor your brights with black.

With our V-necks! And all the neutrals all at once. The Tory skirt with a Uniqlo V-neck (sold out but same diff here), black tights, tan Gucci ballerinas and a grey Maria McManus blazer (how about this as a currently available, almost identical alt.)

Or go full color wheel! High Sport sweater, freshwater pearls, black opaque tights and Jimmy Choos which are somehow $100 cheaper at MyT…for now?!

A Coat With Its Own Coat

Is it just me or did the trend in outerwear shift to the bizarre OVERNIGHT? Like, the furry, shaggy, hairy, textured variety. What happened? I’m halfway through winter and all of a sudden I just want to wear outerwear with its own hair!? I don’t think I’m imagining it, you too!? I had actually started planning this letter two weeks ago with a different coat but then the vibe shifted so fast that I decided we too needed a pivot!

But here’s the thing about these shags. A huge, poofy, poodle-trimmed coat is A LOT at the office. I was going to save this concept for March, after workwear month commenced but then I happily stumbled on this one in Tory’s February lineup. It was fate in the form of a slightly flatter-in-its-fluff car coat!

I wore this coat on Wednesday to lunch at Union Square Cafe. I was frazzled and accidentally went to Gramercy Tavern first where I proceeded to wait 10 minutes before I double checked my calendar invite. I tell you this because I got compliments on my coat while sitting in the hostess’s corner by multiple people! AND also, because if you are in NYC, you know that on Wednesday there were 30MPH winds. Let me tell you, this baby is windproof!!! It seems lightweight, but then it epically protected me against the grid-like city elements.

It is lighter than a shearling. More the type to carry us into spring, but if you too woke up last week and realized none of your coats were quite shaggy enough, consider this one. First though, we have to talk about fit. This is an oversized coat. For reference I’m 5’5” and a size 4, wearing an XS. So if you are smaller than that please, consider this scale (you may need to do some tailoring.) For the rest of you, let’s appreciate that the oversized-ness of this shag lets us easily layer a blazer or big sweater underneath AND has some sort of windproof lining that I can’t quite make out but really enjoyed when I was fighting headwinds on Park Avenue South.

The shaggy coat with my favorite combo of a fun skirt, grey knit and ladylike shoe. &Daughter sweater, CDLP crisp white tee sticking out, the green “ostrich” Tory skirt and Roger Vivier pumps from our first ever workwear month two years ago. Still iconic!!!

The brown shag is excellent over pink! My new St. John suit that I will find any excuse to wear lately. With heavy black accessories to not get too…Barbie? A fun realization about all this color I’ve been experimenting with (yes brown counts as a color!) is that it lets you just lean into those black accessories in a way that makes them feel more like part of an outfit than just…the bag in black. Jimmy Choo oversized tote and The Row oxfords. I love the perfect round toe on these guys but here is another nice looking pair too. And if you’re really bold, these!

The shag over a simple combo of grey skirt + silk shirt. It’s all about the grey and brown combo for me. Fresh! Souer blouse from our most recent 5 Great Things, Aritzia skirt, sheer tights, Saint Laurent boots and Tory belt which is lucky thing No.5 at the bottom of this list.

And most importantly, as we soon leave the deep pit of winter behind us, the greatest aspect of a coat with big armholes: room to layer a blazer underneath comfortably!!!! The shag coat over an Officine Generale blazer (many moons old but how about this one, on sale!?) Auralee jeans, white CDLP tee, Tory’s new Romy bag and buckle boots…which I’m about to tell you about.

A Flat Black Boot…

that gives the dressy vibes of a heel. This boot is better with pants. But there are A LOT of pants-at-the-office days (even for skirt devotees such as myself!) in winter. The placement of the mini buckle on the toe of these boots is just SO fantastic sticking out of a flared or pleat front trouser. It’s size reads slightly dainty on an otherwise shiny, tough boot. And its sheer existence gives the otherwise pretty standard boot a subtle point-of-interest. I’ve been wearing them consistently since receiving them a few weeks ago to start these test drives. I even love them with a straight jean for those no-dress-code-types. They were a hit at school drop off with distressed jeans, a fuzzy sweater and big shearling last week and their shine made them fancy enough to then wear to dinner with black tights, my leopard mini and a grey knit. So consider them for work, but then just wear them all the time too. Which you will need to do since they are stiff and will require a bit of wearring in. Might I suggest a thicker sock til they mold to you to protect those feets?

A close up in the sunshine with navy blue pants.

The full picture. The boots in question with a retro-looking sweater vest, also Tory Burch), a leather blazer (this one is a steal!) flared navy pants. Something about the buckle makes the whole thing feel not overly masculine. I otherwise might want a more dainty shoe….solving an actual conundrum on a cold day!

They’re also really nice with a cropped pant. Gives theme a bit of a “riding boot” feel without the stiffness of sitting in a tall riding boot at your desk all day. With Maria McManus pants a Lisa Yang short sleeve sweater over a plaid Khaite button down from the RealReal. The green is gone but this beautiful blue is on sale. And this stripe looks like the right idea for layering.

AND DON’T FORGET ABOUT OUR BROWN SUIT!!!

A Lunch Bag

Not a bag to hold your lunch but a bag to take to lunch. Sometimes we need a bag that does not require fitting a laptop but fits just the necessities. I remember being at the Fall 2024 Tory Burch show last February (when they introduced this bag shape) and seeing it come down the runway. Literally, moments before the show started, friend of 5 Things Ramya G. said to me: I just need something little to carry papers or my i-pad to meetings! And then down the runway pranced this bag!! (It also comes in a bigger size that DOES fit a laptop). I have loved it ever since and they keep coming out with new fabrications. I’m currently very into the yellow snakeskin here, but also this shiny taupe is stellar. It’s super slim so could easily slide inside your big tote in the morning.

The bag in question with a rubberized car coat, old Miu Miu skirt suit (here is a cute, similar one!) and Toteme boots.

The lunch bag with some easy tailored separates. A riding blazer from The Gigi (here is my dream blazer as an alt? Hehe), B Sides t-shirt, old cuffed trousers (might I suggest these and then have the tailor add a cuff when you hem?) and Khaite sock boots. But the mini buckle boots would be great here too.

A Dark Brown Suede Belt

I fell first for this belt’s buckle. I saw it in white in the Tory Burch Resort 2025 lookbook months ago when I first got to peek at their February drop and I never forgot it. It can be so hard to find a belt buckle that is both subtly interesting and unbranded for the workday. TB offers this belt in multiple colors and textures but it’s the dark brown suede for me, if we are going to declare it a workhorse. It pairs perfectly with both black and navy without announcing itself too vocally (in the way a light brown/tan or shiny croc could.) Other winning factors? It’s the goldilocks of widths. The covered buckle rids you of the feeling of hardware overload, especially if you have little buckles on your toes and possibly zippers on your jacket. Plus, as mentioned above, it’s logo-less. I know I never say never, but it’s been 20 years in this industry and have yet to change my mind on logoed belt buckles. They are just a NO in my book, especially at work where you really don’t want a brand doing the talking for you. I’ll stand down off my pedestal now, but I just had to say it.

The belt as a perfect little accent with black and white and navy and tan. Miu Miu suit jacket (but how about this cropped guy) with a navy cashmere polo (here is a good one), over a white t-shirt, my Foshay skirt, the TB buckle boots and topped off with pearls.

The belt as a grown up addition to my glorified school uniform that I can’t get enough of. Old prada mohair sweater, bought secondhand. This one looks great and prob softer. Aritzia skirt, Tory Burch belt and Jimmy Choo pumps. You can add this outfit into my new “sportswear” era uniform with the green skirt/lace cardi above. Dress for the life you want!? I want to run an American fashion empire circa 1945 ala Empresses of Seventh Avenue apparently. Not NO!

It's great even without belt loops! From left: The brown suede over a black (or navy) blazer! With an old Celine skirt (how about this or this!?) old Prada pumps but remember how I really want you to get the Khaite ones!? And at right, the belt over your vest/dress. I realize this might be too short for some of your workdays, but you could do this same thing over black pants too. Try it if your vest is at a stalemate?! Over a FdL turtleneck (Cos is great too) Attersee dress and Tory slingbacks

And I dont really think you need instruction on how to wear a belt on your pants so here is me trying to push the limits. Black pants (I had to size down in this pair) with the brown belt and and brown boots (these are Chanel via TRR but also these are giving the right toe shape.) Shirt as jacket over your wackiest t-shirt. This is a High Sport one off, but your most fun stripes would be great too! It’s all pretty tame once you put it together, no?

That’s all for today! No boring outfits. All (most??) work ready! Love you guys. And happy Sunday.

Yours TRULY,

Becky