How to look stylish without trying. Full disclosure, this is how my day looks most of the time (it was different when I would go out to work). I get up in the morning, shower etc. then I take my dog for a walk. I get home, sit down and do some writing, answer emails, check social media. I might look for companies that I want to work with or write some pitches. Sometimes I’ll meet a friend at a coffee shop or run some errands. Then I take the dog out for our afternoon walk. I have an early dinner and head out to a ballet class unless I’d already been to the gym in the morning. In the evening I  journal or do some more writing. Lately, I’ve been researching some real estate ventures we are looking at getting in to.

As you can see much of my day is spent by myself or with my dog. While I may not technically be sitting in my pajamas my “writing outfit” isn’t far off. I’ve tried the coffee shop writing thing and while it’s possible for a few minutes here and there I just can’t concentrate long enough to be productive. In addition to that, an old hamstring injury means that sitting upright on a hard bench or chair for long periods of time is uncomfortable. Besides, I think that the whole experience is romanticized and not that conductive to productivity for long periods of time.

What am I getting at? Well the one constant in all of this is that I don’t see any use in putting a big effort into my clothing when no one is seeing them. I also hate looking frumpy and I hate looking messy. Actually, one of the reasons I don’t wear my good clothing on a daily basis is because I don’t want my expensive pieces to get ruined. So I’ve decided that there has to be a trick to looking put together and stylish without actually trying (and this is especially true when your friend calls at the last minute to invite you out and you have zero time to plan).

HOW TO LOOK STYLISH WITHOUT TRYING

Have A Uniform. This is going to be my most important point. Have a casual outfit that you can always count on. I just bought the best skinny jeans. They fit like a glove, are super comfortable and worn just the way I like them. Best of all, they go with everything. Then all I need to do is pick my go to top. It’s black, fitted in the arms (it gives me a slim look) and then flares out around my waist, a part of my body I don’t like to highlight. I add my minimalist gold chains, black ankle boots and I’m usually good to go. It’s really that simply. The sheer fact that everything fits and that I feel good in the outfit makes me more confident. While it might not be the most exciting outfit I look good and that’s the important part.

Mix Styles. I think this is very important to consider as well. Remember that whole grunge moment in fashion history where everything we wore was plaid and holey and scuffed? Everyone looked like they hadn’t showered in months. That’s not a good look, ever. Ripped jeans looks great (I will always love them) but they look so much better when paired with heels or a button down top or some nice jewelry. It’s no different when you walk into a coffee shop to see someone dressed up within an inch of their lives, it’s too much and borders on the ridiculous. Comfortable mixed with class is always the best combination.

Wear The Right Underwear. No matter how expensive your clothing is, no matter how tailored your pants are if your bra and underwear don’t fit right or aren’t the appropriate type you won’t look good and it’s just as simple as that.

Make It Your Own. We all have that one piece that we absolutely love. Mine is a long lariat style necklace in green and gold. It adds instant interest and colour to my outfit. Since it’s long it’s something I can play with if I don’t know what to do with my hands. I don’t know if that’s the right way to think about it but there you go.  Of course it doesn’t have to be a piece of jewelry. You can wear a scarf or carry a purse, anything really, it’s completely up to you.

If all else fails then have a red lipstick on hand. I’m serious, I must have repeated this tip on these pages a hundred times in the past few years but it’s so true. There’s a shade for everyone (I’ll be so bold as to say Armani 400 or 401 will work on every skin tone) and a consistency for everyone and it’s likely that you will be the only one wearing red and by default will look cool and confident.

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