37 Trendy And Casual Outfits To Wear Everyday

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Do you have a go-to outfit? You know, that fool-proof, fail-safe look that you resort to for more occasions than you’d like to admit? While many women do have their tried and true, often what happens is that it starts out looking great, then becomes faded, worn and – yikes! – begins to look frumpy. Yet knowing how to recreate this perfect combination of chic, casual and comfortable can leave you feeling more than a little anxious. Have I hit a nerve?

If you’re like most women, putting together an outfit is not something you look forward to. In fact, it may very well strike fear in the hearts of many as you visually appraise the contents of your closet. Then when you open the door you stand there and stare. Blankly. With little or no inspiration. And grab, once again, your go-to outfit. Chances are at least one item is black. And chances are, when it comes right down to it, you don’t really love it and it’s not doing anything to bring out your best.

But where to even start? Let’s start with the basics. Let me introduce you to ‘Upscale Casual’, which just happens to be the perfect blend of casual yet chic and is appropriate for many occasions; business casual offices, dropping the kids off at school, volunteering, grocery shopping, client meetings, PTA, book club, dinner with friends, networking events and so many more.

Upscale Casual is what I end up recommending to so many of my clients for work, to wear when they want to look pulled together but low-key on the weekends and for any other time they don’t need to be dressed up but want to look great. While it may seem tricky, the effect of Upscale Casual is what I like to call ‘greater than the sum of its parts’. That is, the overall look is far more polished and chic than the pieces themselves. Here’s how to get it:

1. Start with the Basics – You can start with simple items – jeans and a t, a nice pair of trousers and a tank, even a simple dress. The better quality and fit, the better. Buying the best you can afford [core items] will make something simple into something special. Simple pants and a top are great to wear around the house, the studio or to work, then when you want to go out into the real world, simply throw on your add ons.

2. The Third Layer – There’s something about a jacket or cardigan, aka the ‘third layer’, that just gives your look a whole new edge and makes you feel more polished and pulled together. Your third layer could be a great trench, a blazer, a cardigan or other topper. Choose one that is a great color for you, that fits you to a t without adding bulk and really brings your look together.

3. Shoe In – Shoes for this look can be as simple as you like. Stick with flats or low wedges for best effect and ease of movement. When you’re busy and have a lot to accomplish, wearing high heels or wedges can actually hinder your progress.

4. Accessories Count – This is where you get to punctuate your look and create your signature style. When adding in accessories, forget your tried and true’s and opt for something that will add punch to your outfit. Something that speaks to you and your personal style will pull everything together in a chic way.

5. Go For the Flow – While I am not a fan of wearing things that are matchy-matchy, you do want your look to flow together. That is, everything should ‘relate’ to each other – clothing and jewelry alike – to create harmony. This will ensure that you’re not overdressing or being overpowered by your look. When it just flows effortlessly, it’s just right!

See what Upscale Casual outfits you can create in your closet. Try mixing and matching things in new ways, taking a jacket out of context and pairing it with jeans, and simply pairing things in a way that is chic, yet still has a casual vibe. This should open up a whole new world of possibilities while making it easy to know what to wear everyday – and giving you many options to choose from!

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