A stylist is always going to ask you to try new things when you work together. That’s part of what you’re paying them for. If you wanted to look and feel the same as you always have, you wouldn’t have hired the stylist in the first place. (I mean, let’s be real, right?)

When I work with clients, I take a bit of a different approach. I’ll still encourage clients to try the outfits and pieces that make them uncomfortable. But it doesn’t make sense for you to buy something that you’re never going to wear. You’ll just end up with more clutter in your closet and more decision fatigue when you’re getting dressed in the morning.

Instead, I like to explore why a certain piece or style makes them uncomfortable. Then I find alternatives that still give clients the look and feel they want while also getting them outside the comfort zone of their current wardrobe.

How this concept works

Personally, I hate skirts. When I try them on, I feel immediately uncomfortable–even before I look at myself in the mirror. If something turns you off that much, it’s not meant for you. I don’t like the way skirts can restrict my movements and I start to fidget in them. I don’t want to go through my day fidgeting, so I choose to have very few skirts in my wardrobe (dresses are another matter).

Instead of skirts, I go for dressy shorts, dresses or elevated jumpers. So if you feel the same way, I recommend you give those options a try.

If you’re struggling with stepping outside your comfort zone when it comes to styling yourself, here are some alternatives to some of your most-worn articles of clothing:


If you work in a casual environment, you likely pull jeans out of your closet first. Get yourself out of the rut and branch out with different colors, patterns and styles of jeans. Or go for a more comfortable casual pant or slack with some give and stretch or in a heavier fabric. The options are endless!


This is the go-to for many busy moms who need something to wear to the soccer field. But then it becomes the weekend wardrobe. Before you know it, you’re wearing T-shirts to work too. Luckily, designers have caught on and now offer tees in silks, linens and other fabrics that make it easy to wear a T-shirt without anyone even noticing. But you’re as comfortable as ever! Better yet, throw a blazer or tailored jacket over a dressy tee for a different look.

Shorts & Tanks

Some people just aren’t comfortable with shorts at all, yet live in an environment where shorts and tanks seem to be a must. It may not be the skin showing that’s the issue but rather some body image self-consciousness to blame. Longer shorts, skirts or flowing joggers are a good alternative for shorts. Muscle tees or cap-sleeved blouses are a go-to’s for tanks, or a nice blazer or sheer button-down over top.

In this day and age, there are so many options available. Long gone are the days when women are expected to wear a certain type of clothing and ostracized if she doesn’t. So have a little fun, step outside your comfort zone but don’t try something that is so far from being your style that you’ll never wear it.