How to Dress Comfy Without looking like you've given up

Every few days, a friend of mine invites to meet her at a fancy social club located in the heart of downtown.  It's a posh professional lounge with beautiful city views.  I've become somewhat masterful at turning down her generous request.  The thought of having to break out my business casual attire from my past life sends shivers down my spine.

 I've become fully immersed in a world of wearing casual, comfy clothing.  The thing with casual attire is there's a thin line between looking cute & comfy or looking like you've totally given up on life.  I have to admit that I've been guilty of crossing that line.  There have been times where I've silently prayed asking that I don't run into anyone I know while running errands.  That's not the way to live.

If I'm going to be a lifelong comfy dresser, I might as well learn to do it right.   There are certain rules that one must abide by that allow us to sport casual clothing while still looking like we care about ourselves.  Let's discuss.


Never go full baggy

Oversized clothes are the epitome of comfort wear.  With loose fitting clothes, we don't have to concern ourselves with certain details.  Baggy clothes always fit so they sometimes become a default option.  A while back, I made the commitment to avoid baggy clothes as much as possible. Whenever my wardrobe consists mainly of loose-fitting clothes,  I'll start to put on weight. It never fails.  Worst of all, I don't realize what's happening until it's too late. By then, my "normal" clothes barely fit.  That's why I've taken an oath to mix baggy and fitted items whenever possible.  One negative view of baggy clothes is that you didn't put much thought into your look. Pairing it with a fitted item balances out the entire outfit.  Suddenly, your clothing choices appear intentional. Not like you threw on what you had available until laundry day.

Accessorize Strategically
The easiest way to elevate lounge wear is by mastering the art accessorizing. The great thing about applying this strategy is that you have multiple options.   I like to layer on various tiny rings, chain bracelets or sparkly studs.  It really doesn't matter your jewelry preference, as long as you add something that requires an additional step. In doing so, you're sending a message that you care about the details.   And that's super important if you're a serial comfy dresser like me.

Add High-Quality Items
If you want to take your accessory game to the next level, you should seriously consider investing in a few designer pieces. A quality bag and the right pair of shoes can go a long way towards transforming your simple look into something magical.  Years ago I made the decision to stop buying a bunch of trendy clothes and redirect my finances towards securing high-quality pieces.  Best decision ever.  Now, I can walk into almost any situation and still get compliments, even when I'm wearing basics.

Fix Your Face
One habit I've been cultivating is to avoid walking out with a completely bare face. I don't have to go all out, just a 5-10 minute natural face routine is enough.  Once I experimented with going to Walmart with a full face just to see what difference it made.  I noticed a lot more looks than normal and a couple people even approached me.  I go grocery shopping pretty regularly and most of those trips are pretty uneventful.  But when I put in a little more effort in my appearance, I attract more.  People react to you differently when you present the best version of yourself. This even applies to you.  When you feel good, you make different (better) choices. Imagine the compounding effect of you looking and feeling good day after day.  There are real benefits to be had.  Take full advantage.

Invest in Quality Leisure Wear
One area I need to do better in is to sport better-looking loungewear.  I have to admit that most of my comfy clothes were bought for the purpose of wearing around the house or while running errands.  Needless to say, I didn't invest much in them and they look unimpressive.  Nowadays, athleisure is all the rage and the choices for designer active/loungewear is endless.  One of my goals for the remainder of the year is to toss out most of the stuff I have and replace with hand-picked quality pieces that are both stylish & comfy.

Focus on Your Signature
Lastly, I invite you to define a signature item that you'll maintain even when you're wearing a laid back look.  For some, that means maintaining immaculate nails (which looks great when you're wearing casual gear) or making sure your hair is on point.  Doesn't have to be fancy. Just make sure you have a few hairstyle options that typically attract compliments.

Once you've established the most complimentary hairstyle or accessory, you can dress down all you want and still demand attention when you walk into any room. Also remember, when you're dressing down, there are certain details that can't be missed. Your skin must appear to be healthy and hydrated, Your clothes must be in good condition.  You have to look like you put some thought into your look.  If these requirements aren't met, you end up looking like you just rolled out of bed and put on whatever was within reach.  That's not a good thing.  This is what leads to silent prayers hoping that you don't run into anyone you know.  Lucky for us, this situation is completely avoidable.

If you're looking for more inspiration on dressing down and looking pulled together, you'll find some great ideas by paying attention to paparazzi pics taken at an airport.  These celebrities are often dressed down yet they know there's a decent chance that they'll be photographed so dress accordingly.