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What to Wear When You Don't Know What to Wear

Updated: Jan 10

We've all been there. You get up in the morning or you have a dinner to go to and you don't know what to wear. You don't need to put on anything crazy but nothing is clicking. Here are 7 outfits to wear when you don't know what to wear.


Jeans + T-shirt + Blazer


Simple but fabulous. This formula is timeless and looks good on everyone and almost everyone has it in their closet. If you don't have a blazer, I would reccommend it. It's such a great way to feel put together without even trying and I find that it fixes up a lot of my outfits. Throw on your favorite pair of jeans and your favorite t-shirt and you should be feeling pretty good. Then all you need to do to complete the outfit and elevate it is a blazer. I always reccommend a little but of an oversized one. This way it kinda goes with everything and its comfy. It's more versatile and in the winter you can wear a big sweater or sweatshirt under it and it still looks put together. My example below includes some basic sneakers and cute accessories that add a little personal style to the outfit. You'll see me in this outfit year round.


Blazer - Anine Bing

Jeans- Levis

T-Shirt- Everlane

Sneakers- Adidas

Earrings- Jenny Bird

Sunnies- RayBan


What to wear when you dont know what to wear

Midi Skirt + Graphic T-Shirt + Leather Jacket


This outfit is one of the more 'complicated' choices. If you want to look a little more dressed up while still feeling comfortable and put together, I love this uniform. Everyone should have a plain black midi/maxi skirt in their closet and a fav graphic tee. It can also work with a shorter skirt, which is the beauty. It's simple and versatile and works in almost every version. Because the skirt below is a sily midi, it gives it a bit of a girlier feel. Meanwhile pairing it with a graphic tee and a motor leather jacket adds some edge. I guarantee you'll get compliments on this outfit.


Jacket - COS

T-Shirt- Anine Bing

Skirt- Aritzia

Sneakers- Adidas

Earrings- Jenny Bird

Sunnies - Ollu


What to wear when you don't know what to wear


Black Denim + Sweatshirt + Boots + Belt


If you choose all darker pieces and add some accessories, you can elevate any look. I love the idea of dressing up a sweatshirt because it can make you feel more comfortable when nothing feels right. The Anine Bing sweatshirt pictured below is one of my favorites. I have another version of it that I often dress up. When elevating a sweatshirt it's best to pick a basic color (think navy, grey, black or brown). Then throw in some boots and accessories and suddenly it's more than a sweats outfit. This is something I opt for when none of my tops seem to be fitting right or when I'm not feeling 100% in my own skin. You can also dress it down with sneakers and lighter wash denim.


Sweatshirt- Anine Bing

Jeans- Agolde

Boots- Reformation

Earrings- Jenny Bird

Belt- Anine Bing

Sunnies - Ollu


What to wear if you dont know what to wear

All Black + Leather Jacket


This is a staple for a reason. It's easy and fashionable and everyone has it in their closet. Simply pick your favorite dark wash jeans, a nice black top (the simpler the better) and your leather jacket. Accessories are encouraged, I went with a bit more of a statement earring here to add some fun because this is a much simpler outfit. I also love the idea of adding a belt here as well. I've been going with a lot of bigger accessories lately to add some fun and flare to outfits. You always look more put together with great earrings. I also think it allows you to show some personal style and character on an otherwise simple outfit.


Jacket - COS

Jeans- Agolde

Boots- Reformation

Belt- Anine Bing


What to Wear When You Don't Know What to Wear

Maxi Dress + Jean Jacket


A black simple maxi dress makes any outfit effortless. You look put together without even trying. In the winter sometimes I'll throw on a black sweater over the dress but this skims one is so versatile and easy I really recommend it to everyone. I love wearing an oversized denim jacket too. I have a great vintage levis one but if I didn't I would buy this agolde one. Agolde is one of my favorite denim brands and they did right with this jacket. Throw on sneakers and some accessories and you'll be cozy and fashionable all at once. Each of these pieces are items you probably have some version of in your closet so go try it on and I'm sure you'll feel good.


Denim Jacket- Agolde

Sneakers- Adidas Earrings- Jenny Bird

Sunnies- RayBan


What to wear when you don't know what to wear


Jeans + T-Shirt + Coat + Statement Accessory


Sometimes you don't want to put together an outfit. When that happens I like to wear my same old favorites- jeans and a t-shirt plus a coat in the winter. To add a little fun, I'll wear a bright pair of shoes or a fun bag. These hot pink shoes add a little color and pizazz to a simple outfit. You are likely to get compliments on your accessories without taking too much risk with your basic outfit. I'm a sneaker girl so I like to get fun sneakers but this could also be great with a red boot, fun flat or anything in between. When you wear lightwash jeans and a white tee, you can match it to anything, which makes it the perfect base in this example. Another way to go can be a fun bag-- I added two of my favorites in the links below too.


T-Shirt- Everlane

Sneakers - Adidas

Jacket- COS

Bag- Daniella Lehavi

Earrings- Jenny Bird


What to Wear When You Don't Know What to Wear


what to wear when you don't know what to wear


LBD + Jacket + Boots


Maybe the most timeless of all is the LBD. If you have the right one it can basically be worn in any scenario. I paired it here with a denim jacket and boots for a more dressed down look but you can add a leather jacket or a longer coat and tights for a warmer and more elevated look. There's nothing sexier or classier than the LBD if done correctly. This Norma Kamali dress is an absolute winner but the key here is having one that feels comfortable on you. If you have a little black dress you love you can make 100 different great outfits with it year round.


Denim Jacket- Agolde

Black Dress- Norma Kamali

Boots- Reformation

Earrings- Jenny Bird

Sunnies- RayBan


What to wear when nothing seems right

Final Thoughts


The key to this guide is that I reused the same pieces over and over. Most of these outfits contain my favorite pieces that I feel comfortable in. When you don't know what to wear you want to make sure you start with something you love and feel good in. If you start with that piece, whether it's your favorite sweatshirt, denim piece or LBD, you can use one of these formulas around that pick to feel good in your outfit. Use accessories to spice it up or go classic! Classic is classic for a reason. To shop more basics, check out this article about capsule wardrobe essentials.


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