Tips on How To Dress CasualRecirculating this blog post because I still love the idea of dressing casually but still keeping everything polished and elevated. This post originated from a lunch with a girlfriend where I was wearing an outfit similar to the above picture and she remarked at how comfortable yet not messy I looked. I think her exact words were “how can you manage to look so relaxed yet still so put together?!” Not that I wanted this post to be tooting my own horn (though I am never against some positive self talk – I did look cute that day LOL), but that conversation gave me an idea for a blog post!

When approaching a more comfy and super casual outfit, I instinctively look for certain things, add particular elements, wear clothes with specific fits and find ways to elevate the look without sacrificing on the comfort factor. So I thought I would share my tips on how to dress casually without looking sloppy. Originally I had 5 tips for this blog post but I’ve decided to add on a few more that felt relevant. I’ve also rounded up a bunch of outfits that help to illustrate my tips and give you an idea of how I approach dressing comfortably and casually yet still feeling put together.

How to Dress Casual

Add Accessories

How To Dress Casual in winterCoat | Sweater | Joggers | Sneakers | Hat | Bag | Mittens

How To Dress CasualJacket (similar) | Scarf (similar) | Sunglasses (similar) | Joggers (similar)

One of the first ways to elevate a super casual outfit is to add some chic accessories. Sunglasses, a big scarf, hats – all of these are great to add to a casual look. It helps make the outfit look more interesting and put together. I also tend to buy many of my accessories for winter especially in similar neutral tones so I can mix and match when needed yet everything still looks cohesive.

Stylish Sneakers

How To Dress Casual in the coldCoat | Sweatshirt | Leggings | Socks | Sneakers

trousers and coat outfitCoat | Turtleneck | Trousers | Sneakers | Sunglasses | Bag | Hat

Sneakers are most of the time going to be my go-to when dressing down or wearing something very casual. I have purposefully looked for sneakers that are less “athletic” looking and more “lifestyle” looking. Does that make sense? There are definitely those types of sneakers that are best for working out and look like a workout sneaker. But then there are a ton of various styles that have a more everyday stylish look to them. Those are what I seek out for my casual looks.

Golden Goose Sneakers

Though Golden Goose sneakers can be somewhat controversial because they have a worn in “dirty” look and cost an arm and a leg, the look of them is what made me start wearing sneakers in my day to day life many years ago. I only owned one pair of sneakers for most of my 20’s and 30’s when I lived in NYC and spent 90% of my time in super high heels. I loved to dress up and sneakers didn’t fit my style. But when Golden Goose sneakers came out, I liked the idea of a fashionable type sneaker that I could wear with dresses, pants, etc and not look like I just got back from the gym. Since then I have seen a ton of more budget friendly versions of this type of sneaker and love it!

New Balance 327

Besides a fashion-style sneaker, many of the athletic sneaker brands have made styles that look so chic and wearing for day to day. The New Balance 327s specifically are some of my favorite because of the slightly pointed toe so I actually find myself wearing them with leggings, trousers, jeans, etc. They are SO comfortable yet manage to look so chic and polished.

Wear Your Jewelry

casual fall outfitCoatigan | Sweatshirt (similar) | Leggings | Bag | Necklaces here and here | Sunglasses | Sneakers

Don’t save your jewelry only for your fancy outfits! Layer up some of your favorite necklaces, add some small hoops or wear your everyday bracelet stack with all your casual looks. Jewelry always levels up any look but especially a casual or comfy outfit! I prefer to wear my jewelry with just about anything. Even if I plan to lounge around the house all day, I will still add my daily jewelry because it makes me feel good.

Pick a Slimmer Fit

How To Dress Casual in fallSweater | Joggers | Bag | Sneakers | Sunglasses

The oversized look can be cute for certain styles of clothing, but when dressing casual I mostly like to avoid clothes that are too baggy and stick to a more tailored/slimmer fit. The joggers I am wearing above is a good example of this. While they are still roomy and comfy, the actual cut is slimmer throughout the legs and I love the fitted ankle.

Pick a Monochromatic or Matching Set

matching set casual outfitSweatshirt | Joggers | Sunglasses | Bag | Sneakers

matching set casual outfit ideaHalf zip | Joggers | Sunglasses | Bag | Sneakers

Nothing looks as pulled together as a matching set! And especially when it comes to a lounge set or athleisure look, wearing all one color looks chic and purposeful. I love that there are so many more options now of matching lounge sets so it makes looking put together much easier and honestly, it makes getting dressed less stressful. I don’t have to worry about trying to put together a casual look because I just grab one of my matching sets and the work has been done for me.

Stick to Neutrals

quilted jacket outfitJacket | Hoodie (similar) | Leggings | Bag | Sunglasses | Sneakers

Matching sets are great but another easy way to put together a comfy, casual outfit that looks polished is to stick with neutrals. Black, white, cream, tan, gray – it’s best to buy your athleisure pieces in these colors because it is easy to mix and match to create cohesive looks. It’s fun to throw in a bright color from time to time but having basic colors first should always be a priority when shopping. Also, don’t shy away from choosing different textures because that is another way to create an interesting and chic outfit while still keeping the look in all neutral tones.

Do Your Hair and Makeup

How To Dress Casual with leggingsPullover | Leggings | Sunglasses | Bag | Sneakers

Choose one or the other (or both if you feel inclined). I find that doing my hair can make me look more put together, or doing a bit of makeup with a cute hat achieves the same level of polish. Most of the makeup looks that I do are natural and suitable for everyday so they work well with both dressy and super casual looks.

Invest in Nice Flats

cardigan and jeans outfitCardigan | Jeans | Bag (similar) | Flats | Sunglasses

I have always been a heels gal but over the years, I have made a point to add some chic flats to my wardrobe. My preference is closed toe flats rather than something like flip flops because they are suitable to wear year round. There are some days when I don’t feel like wearing sneakers or ankle boots but want my feet to be comfortable so that is when I reach for my ballet flats or comfy loafers. And especially if you work in a business casual workplace, it’s good to have stylish flats to wear to work but also would be great for the weekends.

Try Trousers

casual trousers outfitSweatshirt (similar) | Trousers | Bag | Sneakers

I know, I know. Trousers don’t sound like the most appealing item of clothing when you want to be comfy but trust me on this one. Trousers don’t just have to be worn with a button down shirt or collared shirt, they are one of my favorite casual clothing items in my closet. Slightly loose yet tailored trousers can be as comfortable as joggers. And they are SO versatile! You can obviously dress them up and wear them to the office, but throw on a comfy sweatshirt and sneakers to make them work on the weekends (or the office if you have a casual dress code).

Get a Graphic Sweatshirt

Graphic Sweatshirt with jeansSweatshirt (similar) | Jeans | Shoes | Bag

I absolutely LOVE graphic sweatshirts and have myself collected a few over the years for when I want to dress down but still look chic. Anine Bing makes my favorite sweatshirts because they are the perfect oversized fit and are not too heavy to wear year round. But there are a ton of other brands that make chic graphic sweatshirts at all price points. It makes the look a bit more interesting and cool but you don’t have to sacrifice on comfort.