Let's Ask Maggie!: Fashionable or comfortable and confident?

Dear Maggie,

In general, my attitude toward my personal fashion is "I do what I want!" and I think I pull off most outfits (or at least I don't look like shit), but I don't think I'm very good at being trendy or classic or anything remotely stylish. So what is more important, in your opinion: being actually fashionable, or being comfortable and confident? Is my #winning attitude actually the accessory I'm counting on it to be? (*disclaimer: I spend a shitload of time in construction gear, but I don't count any of that as remotely fashionable).

Rachel  B., Chattanooga, TN

Hi, Rachel!

This is probably my favorite question that has ever been submitted to Let's Ask Maggie!. So #braggingrights on that! I feel you on the "I do what I want!" mantra. My family can tell you I came out of the womb with that attitude.

Let's break your fashionable vs. comfortable and confident question down one step further. I don't think it's an either or, I do however, believe that CONFIDENCE is the most important fashion element. So, your #winning attitude really is the accessory you hoped it would be! Congratulations! :)

For you, comfort makes you confident, for others it might be a 4" stiletto or a dusty pair of Wranglers. You can pull any look off as long as you feel good while you're wearing it. (Know your audience too. Don't show up to a black tie affair in a tank top and cutoffs because I said confidence is what's important.) 

When working with an individual client I have the client go through their closet and individually pull garments out to show me. I do this so that I can see their expression as they hold the piece. If their face looks like they just ate a handful of lemon Sour Patch Kids that item goes right into the give away bin. If that is how they felt holding it, how on earth did they feel wearing it?! 

I'll also let you in on a little secret: even stylists make mistakes. It doesn't happen to me often but I can tell you right now, if I put together an outfit, leave my apartment, and realize later in the day that I hate it, or it feels weird, or it's just not right for whatever reason, I will go home and change before I head to a meeting or an event. It is hard enough to walk into a room full of strangers without feeling like I look terrible on top of it. If I'm in something I feel my best in, by the end of the night everyone in that room will be my best friend. If I walk in wearing something I hate I'll just stand to the side the entire night bored. Clothes have more power to them than most of us realize. My greatest hope is that you have a closet full of clothes that only help you exude confidence and that you have the courage to rid yourself of the things that do not. 

In the meantime, continue to rock that construction gear!

How about you, readers? What is most important to you? Fashion? Comfort? Confidence? Give me the scoop in the comments below!

With love,


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