I have the pieces, but I still can’t get dressed…

So you read the Substacks, you bought the things, and your closet is full of clothing... why do you still have “nothing to wear”?

Shopping is easy, especially today. Everything is at our fingertips and it is so easy to find something to want. We all want to want. We love to want!! But what happens once you get home, new item in hand? Why does it always feel like this thing that we thought would change our wardrobe (and our life!) just gets added to the pile of disappointing purchases? We will maybe wear it once or twice (or let's be honest… never), but it never quite measures up to the expectation we imagined.

I have personally been there MANY times. A jacket that a substacker or influencer swears they wear “on repeat” doesn’t offer the same utility in my wardrobe. Or the promise of the “world’s best t-shirt” actually feels a bit too tight in the armpits, but oops, I already ripped the tag off. For me, the first step in getting out of that cycle is forcing myself to be less desperate and more discerning. Just because someone loves a t-shirt or a pair of jeans, why do I assume that I have the same taste, criteria, and body as this stranger and it will be equally as perfect for me? I have instilled a very strict 24-hour rule, which seems really easy to abide by (And it is! That's what is so great about it!), but it really takes away that desperation and impulse. The jeans that someone else loved will still be there tomorrow. I can think about it, mull it over, and then decide with a clear mind. Often, the decision is that I don’t need them. The clearer you are on your own style, the easier these decisions become, and the less I am looking to see what others are purchasing. When I am clear on my style, I can appreciate others without feeling like I need to have what they have. Easier said than done, I know!

But what if we do buy the thing? And we have a closet full of things but still have NOTHING TO WEAR!

I have pretty much made my business out of this conundrum, offering one-on-one styling sessions where I help clients edit their wardrobe, find their style, and integrate the things that they LOVE but don’t know how to style.

I might put myself out of business with these tips, so get ready….

@asiatypek / @amaliemoosgaard, @ceciliemoosgaard

Next time you are getting dressed and struggling to style a piece (whether it's a “basic” or a “wildcard”), think about these questions to get you started.

But before you start… let's set the scene. I often suggest trying this exercise when you initially bring home the piece and are excited about it. Give yourself a little time with it. Do not try to style it in the morning when you are rushing or right before you are meant to meet up with your friends at dinner. Take 10-15 mins to play with it. Relieving that time crunch and pressure will allow you to be more creative and lower the stakes. If something doesn't work, we have time to figure out why it doesn’t work and adjust.

I find that often, we will get frustrated and give up easily on a piece, and then it will get regulated to the closet as something that just hangs there and never gets worn. Therefore, giving yourself some time to be creative will increase the chances that this thing actually makes it out of the closet. After all, you bought it, you have it… so you might as well wear it!!

1. What did I envision wearing with this piece when I had to have it…?

• This question really helps get at the why. Why did I even buy it? What was I hoping it would achieve? Did I think that this slimmer sweater shape would be great with the jeans that always feel too slouchy with a thick knit? What was my vision here?

• This is a fun one because sometimes, when I ask clients this, they simply say, “I had no vision; I just bought it.” Which is okay! But that is not necessarily the most thoughtful approach. Oftentimes, however, we will have an idea. And this idea is always just a great place to start.

• So for example, expanding on the slim sweater hypothetical, if I bought it with the intention of wearing it with my slouchy jeans, let’s start there. Does it work? If so, great! Maybe it will work with other slouchy bottoms as well? If it doesn’t work.. why not? Is it too slim? Not slim enough? Take that extra time to figure out what isn’t working so we can workshop it and try something else.

  

  @sandrasemburg / @alexcarl

2. What was I wearing when I tried it on?

• This is a huge one. I have found that SO many clients make purchases IRL because the piece looked good with what they were wearing when they tried it. (If it looked awful, you probably wouldn’t get it!). So, if you are struggling to style something, think back to the moment you tried it and what you were wearing.

• I have a personal example: I had a kind of 70s floral top that was a bit of a wild card in my wardrobe. It always felt really hard to incorporate, and every time I tried it with jeans, it felt a little basic. I remember that when I purchased it at the store, I was wearing slouchy chocolate brown corduroys and black flip-flops. Which is not what I would think of styling it with, but it looked so great! The texture of the corduroy and the boyish shape of the pants really added contrast to the floral, and it looked so good that I bought it! Now, I style that shirt with those cords or other pants with texture. That was a huge unlock for me!!

3. When / where would I wear this?

• This is one of the first questions I ask clients when they have a “how” piece. It seems simple, but giving it a use case is really helpful in styling a look around it. Staring at a piece and all of the options in your closet can feel really overwhelming, so this offers some guidance.

• For example, I had a client who had a pair of really cool vintage Gap slouchy trousers. I asked her when she planned to wear them. Was she thinking of wearing these more to work? In the evening? To run errands? This helps narrow it down a bit. For these particular trousers, she said that they were so comfortable that she hoped to wear them on the weekend for running errands. This gave us some context, so we were able to throw them on with an oversized, slinky black t-shirt and black sandals. We also tried them with cute jelly shoes and a graphic tee. The context allowed us to situate them, and it felt way easier to experiment! Of course, we often think of trousers like this as "work pants,” but this client didn’t go into an office, so she was getting stumped. That is why it is so helpful to ask yourself where and when you would want to wear something instead of just creating a look around the vibe or assumed utility of the piece.

@asiatypek / @linazhanglina

4. What is the challenge of this piece? How do we not want it to feel?

• This is probably my favorite tip and the one that I find the most helpful and illuminating for clients. Why is this hard to style? What is it about this piece that trips me up or never feels right? Often, I ask this when clients have a piece that they always try on but never wear out of the house. Sometimes, it takes a little analyzing, but it is usually an aha moment!! I often hear things like— it feels too bright / too oversized / too girly / too masculine / too pretty / too edgy. That is incredible information for us to then take that element and work against it!

• For example, I had a client that said she loved a blouse but she didn’t want it to feel too sweet. The blouse itself was soft and feminine, so my client usually tried to style it with other things that felt similarly sweet. That, of course, was making it worse. Instead of playing into the property that is making it feel challenging (the sweetness), we want to overcompensate or add deliberate contrast. Instead of pairing the blouse with a skirt or light-wash denim, we said, “Okay, what is the least sweet item?” We decided on a pair of leather trousers. The contrast of the blouse with the edge made it feel way more wearable. We also tried it with the Nili Lotan Shon pants, which added a more tomboy and utilitarian vibe, which made the softness of the blouse feel like an ironic twist or an unexpected detail. The look then felt more genuine to her style, and it didn’t feel too basic or straightforward.

5. How have I worn it before?

• This does not always apply, but if a client has worn something once, either successfully or unsuccessfully, I like to hear about that. If it was unsuccessful, I like to push them to try to explain why it didn’t work. Was the proportion wrong? The color? Was it missing something? Often, we can use that as a starting point and then workshop it to make it better. Often, one's instinct is correct, but it just needs a small tweak. So instead of giving up and saying, “I wore this once, it looked like shit,” we can figure out why it didn’t work and then improve it. If a client has worn the piece before and it looked great… that's also great info! They will usually tell me— I wore it one way, but now that is the ONLY way I know how to wear it.

6. What made me keep it?

• I had at least 30 days to return this, but I didn’t… why? What was it that this piece offered or promised that made me hold onto it? This one is a little more of a gut check than anything. It might not help you style the piece, but hopefully, it will help you better understand your shopping patterns and behaviors.

• If you kept it because of the annoyance of making a return or shipping a box, we really need to get over that. We are grown-ups; we do hard things every day; we can print a label and ship a box. You know I am always gentle with you, but this requires some tough love.

  

  @khaite

7. Source inspiration

• Using inspiration to style a piece is so helpful. I have some videos on how to find inspiration HERE and how to create moodboards HERE. I always reference these because I ALWAYS get questions about finding images and how not to fall down an Instagram or Pinterest rabbit hole where everything and everyone starts to look the same.

• Remember, it doesn't have to be so literal. If you have a pair of velvet trousers that you want to style, you don’t need to find an exact photo in order to use it as inspiration. Figure out what is making the item challenging— is it the color? The shape? The texture? Then, find inspiration that might give you a little helpful boost. We can be a little abstract here!

• If you have a hard time and crave something a little more literal, I often rely on the amazing e-commerce stylists. My favorite is net-a-porter, and I often screenshot the way that they have styled a piece on the website for inspiration. It is quite easy— if you have some tricky white wide leg jeans, type in “white wide leg jeans” in the search… they do such a good job creating interesting but wearable looks on that site and I often find great ideas! They do not have to be the exact pair that you have, but seeing white wide jeans, in general, can be helpful!!!

• I also will use inspiration the other way— I will have a screenshot of a look that I love and then ask myself how I can recreate that look by using what I already have in my wardrobe (aka shop my closet)! It really shows that you don’t need the exact items; you can often create a version with what you have. If you are drawn to an image, chances are it is your style / in your wheelhouse, so it is very rare that you won’t be able to create something similar. It is a fun challenge when you are not sure what to wear!

  

  @tidarosvall

Screenshot these questions / prompts in your phone so you have them next time you are feeling stumped and have “nothing to wear!

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Now, here are some pieces I’m eyeing this February…

TOTEME cape, COS cashmere shirt, SOEUR jacket, JIL SANDER bag, LISA YANG silk pants, LE MONDE BERYL boots, COMME SI scarf, STOULS suede pants,

BY MALENE BIRGER midi dress, MASSIMO DUTTI shirt, CITIZENS trousers, LUCASHEVA mules, JCREW twill pants, MADEWELL belt, KALLMAYER skirt

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1. Carter Jacket

2. Bridget Knee Boots

3. Maurice Jumper

4. Regine Jacket

5. The Tote

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Thank you for subscribing! I’m so excited to see how these questions help you when you’re feeling like you have "nothing to wear." Can’t wait to hear all about it! See you next month (or on February 15th if you're a paid subscriber)! Xx