fashion, lifestyle, outfitting, personal stories

How Working With A Stylist Helped Boost My Self – Confidence & Personal Style

For our last article on this month's theme of self-love, I really wanted to expand on the post I wrote two weeks ago about accepting our body changes as we age. A huge part of that journey for me has been trying to rediscover my personal style and dressing for the body I have now. So I hope you're ready for an epic post on this topic because we have so many tips and ideas for how to get that shopping mojo back, I may even have to start making this its own series!!how to shop with a personal stylist

As a quick recap: In my 20's and into my early 30's I was typically a size 2-4. These days I hover around a size 8-10, and that combined with a very short 5'2" frame has proven to be quite the challenge when it comes to clothing shopping. As a result, I've taken to a formulaic approach of bulkier/loose tops and skinny jeans as my go-to look. And while that's all fine and good, I've really struggled with finding pieces that are a little more elevated. I need to get out of dressing by habit and into dressing with intention. I realized that I miss dressing with more confidence in clothing that really feels ME.

So I decided to reach out to my good friend and personal stylist Tiffany Wendel to get her help with some serious wardrobe refreshing. I had already done several rounds of purging in my closet (essential before starting to re-build!), throwing out any items that I knew would never fit again, I didn't feel confident or excited about, or I've had for so long they're just sad. After that Tiffany came over to see what was left... how to hone in on your personal style | coco kelleyhow shopping with a personal stylist will help you after only one session

First off, this gal is such a ray of sunshine and a gem to work with, if you can't tell by that big smile. Her energy throughout the process is so fantastic, and she's positive but also very honest with what works and what doesn't. (PS - she travels!) 

Tiff began by pulling items out of the closet that she (and I) felt were most true to my personal style - and what that style was. Then we refined it even more by only looking at things from the perspective of a fall/winter wardrobe. I struggle the most in this season, because I hate dressing for cold weather!! When we were done, we had a little capsule of what felt very me.start by pulling clothing that feels the most you and use that for your style template

This process felt a lot like what I go through with interior clients, and I love that Tiffany created this visual direction so that I could feel confident that she 'got' me and my style. In color palette, I tend to go fairly dark and neutral, and with patterns I tend to stick to stripes, leopard, and sometimes a little boho floral and fauna. There are certain silhouettes that I'm obviously comfortable with. It certainly helped that I have some idea of what my personal style is, even if there are only a few pieces in my wardrobe that really express it right now.

Tiffany also asked me several quick but thoughtful questions about myself to help figure out what we needed to shop for. We talked about what my 'everyday' looks like as well as what type of events I needed a more refined 'on brand' look for (speaking engagements, dinners, client presentations, etc). She magically, and quickly, honed in on the fact that what I wanted was a 'winter boho' wardrobe; A way to wear my favorite piece (flowy dresses) in the dead of February. But that I also needed fun ways to elevate my everyday look as well.

I provided her a list of items that I wanted to add from things I had thrown out (a good solid blazer, a pair of black boots), and  also put together a pinterest board for inspiration, keeping in mind that these should be outfits I was inspired by but that also felt realistic for my body.

We parted ways for a couple hours and met back up at Nordstrom where she had (again magically and quickly) pulled together an entire HUGE dressing room full of denim, dresses, blouses and shoes for me to dig into. Now, I'm not going to bore you with this part too much because I'm going to highlight all the pieces that we discovered and loved, BUT I will say that the try-on process is something you better be prepared for! My suggestions? Do your hair and makeup so you feel fabulous. Hydrate and snack. And try your absolute best to go into it with an open mind and a fresh pair of eyes so that you can allow yourself to see yourself the way others see you.

After hours and hours of trying things on, and most of them being total fails (because that's what this process is about!) we emerged from the dressing room with some very clear winners and a few strong maybes. I purchased them all and brought them home...how to give your wardrobe a major refresh with the help of a personal stylist

Not surprisingly... there was a lot of black. Ha! But I was really excited about getting a few fun prints and color in there too! Tiffany was great about pulling items in quite a price range for me as well, so you'll see as I start linking to things that some of them were crazy affordable (hello shoes!) while others were splurges. We'll get into that a bit too! how a personal stylist can help boost your self confidence and style skills

Ok, so here's what we were working with when we started. Like I said: my typical outfit. Skinny denim (always in black) with an oversized top, typically paired with sneakers. To be clear, Tiffany is not asking me to throw away anything I love and am comfortable in, in fact here you can see her giving me some styling tips for when I do wear this look. But after our style session I feel more more confident in saying that this look will only be one of many go-to's instead of the only go-to in my wardrobe.

The first thing Tiffany did was make me try on high waisted, straight leg denim. I wanted to die. I did it anyway. The first pair sucked. The second pair nailed it, and she proved me wrong for the first and certainly not the last time that day. Here's why:how working with a personal stylist pushed me to embrace my curveshigh waisted denim does work on short bodies!

As someone who is short, I thought high-waisted denim was cutting me off in a way that made my torso feel even shorter. But actually having denim that goes up to my natural waist - as a curvier gal - really helped show off my body instead of hiding it. A big part of me feeling confident in wearing these jeans is - you guessed it - embracing my body itself. I want to reiterate that a million times over. This style is all about rocking those curves instead of hiding them, but also giving myself a shape that I was always hiding!

And, as Tiffany is demonstrating here - you don't buy high waisted pants just to cover them up. She took my bulky sweater and tucked that thing right in for the proper effect.showing your waist helps define your body shape more

Adding a heel instead of a flat helps immediately elongate the leg too. Apparently I had been doing one thing right all these years in that I always buy pointed toe heels. I love me a classic pump shape, and that's really good for us shorties! Noted!

Another tip that Tiffany brought here is sleeve length. Your sleeves should never fall at the same place your waist does because it creates a line that chops you in half. If you ever see a stylist at work, this is literally the first thing they do, every time, I swear. Roll those sleeves up ladies! Show off your wrists (and ankles!) if you've got 'em!

But she wouldn't let me stop there... how to style your high waisted denim as a girl with curves

Swapping out the bulky sweater for one that hugged my curves without being too tight again helped to create more shape in my body. how to shop with a personal stylist | coco kelley

Here I paired it with a sneaker because: real life. But oh my god these shoes are SO INSANELY COMFORTABLE. Sidenote: if you buy them, go down a full size. These are a 6.5 and I'm usually a 7.5 in flats.

Proof that this denim was really doing its job? Later that day my husband said I looked skinnier and that he liked my jeans. Whaaaat? I don't think he's ever told me he liked my jeans before, nor does he typically comment on what I'm wearing unless it's a dress up day. These jeans are winners.

Next outfit!how to work with a personal stylist to refresh your wardrobe

Ok, so before you scroll down one more photo and wonder if I've lost my mind... this outfit is here to show you the reason why you absolutely need to get clothing tailored to your body. First off, this blouse is a large, and while my chest is also a large, the rest of my torso is not. This is where your personal stylist comes in mega handy, because Tiffany immediately recognized that this top had potential if we take it in around the waistline so it's not so blousy. Once she pinned some of the fabric back, I was totally on board.

Then there were the pants... why it's essential to tailor your clothes to your body

I've been trying to wear the gaucho look forever and it never ever ever works on me, as is evident here. Know why? Yup. These pants need SO much help to work for my body, and I just couldn't even envision how they might work. But Tiffany showed me the way: 

First off, they should be showing the ankle, so they need to be hemmed. Secondly, they need some of the volume around the bottom to be taken out so that they fall a bit more straight and don't overwhelm my shape so much. Tiffany is doing her best here to show ya'll what we mean, but this leads to another pro-tip. When you shop, it's helpful to bring little clips with you to see how items will look if they're taken in a bit here and there. If you really love a piece, then the tailoring is worth the effort!

To be honest, I'm still not 100% sold on these pants, especially because they're a bit of a splurge and a trend, which is a double whammy in my book. Plus, they're a winter fabric so I would only get so much use out of them this year. I may look for a similar style in a lighter fabric that I can ease into this spring instead, but the point is that I LIKE THEM. And I didn't think I would. Or could. And now I'm excited to find similar styles!

Last outfit! peasant dress and leather jacket with suede boots | coco kelley

Remember when I said I wanted to go for 'winter boho' in some of my wardrobe updates? Well, this is it, 100%!!! A leather jacket was at the top of my list of needs that I gave Tiffany, and this one was a fantastic find for the price. The boots are a great style because they a) have a pointed shape and b) don't cut me off in a weird spot, but also aren't too tall. They'll be ideal for wearing with all my dresses! And speaking of dresses, this one is fantastic because the fabric is more of a year-round option (vs. linen, which is what I'm usually drawn to) and while it has that boho feel, it still gives me shape.

While quite a few pieces we tried on were an immediate no, or needed help in the tailoring department, this look was one that was immediately a win, and I can't tell you how good that feels after hours of being in a dressing room. tips for styling the classic leather jacket | coco kelley

Tiffany pointed out a few things around styling here that I love and agree with. First, the neckline is great. It's showing a little skin without showing off the girls so it feels appropriate for any occasion, but feminine and not stuffy. For the leather jacket, popping the collar a bit helps elongate the jawline and who doesn't need that!? how to wear a short cardigan

A second option for layering here is this cardigan. Again, this is where I would have totally pulled out some oversized slouchy cardi that would probably have weighed me (literally) down. Instead we found this one (so affordable!) with a great detail in the back that keeps things just tailored enough to show off my shape. tailored shape in this black cardigan

And here's everything we bought!! I will say, after a long day of shopping I highly advise over-purchasing and bringing everything home to see how they feel after a few days. There are a 2-3 items here that I will likely end up returning for a variety of reasons. The black eyelet blouse (#8 below) is really adorable, but I realized it's super similar to something I already have. The wide-leg pants that I mentioned I'm already on the fence about. And to be completely honest, the striped sweater is a piece where I may try and find something similar to for less. I love it, but the price is a bit high for me, unless I think I'm going to wear it a ton. We'll see.

Otherwise, I'm really happy with all of our finds! Here they are, with all the links below. 

1. la vie (rebecca taylor) striped sweater - $295 | 2. topshop leather jacket - $177 on sale!| 3. paige denim - $229 | 4. sea midi cream dress - $425 | 5. topshop black cropped cardigan - $24 | 6. vince camuto brown suede boots - $60 on sale! | 7. red reeboks - $65 | 8. la vie (rebecca taylor) black eyelet blouse - $250 | 9. rag & bone cream sleeveless blouse - $295 | 10. rachel comey wide leg pant -  $345 | 11. BA&SH stripe blouse - $175 | 12. black stud detail boot - $100

Another thing I learned after trying on a ton of clothes is that there were definitely patterns in what brands worked well on my body! Rebecca Taylor, Rachel Comey and ba&sh were all repeat offenders and that's awesome because now I can hop online and purchase from these brands more. white peasant dress and suede boots with moto jacket | coco kelley

It's hard for me to remember every little tip that Tiffany brought to the table, but here's what I really want to point out from this experience:

IF YOU CAN AFFORD IT, HIRE A PERSONAL STYLIST. Even if it's just for one session. Tiffany helped me break out of my comfort zone, try on items that I wouldn't have otherwise, filled me with confidence in what works and what doesn't and that sets me up for now being able to better shop on my own! In fact, immediately after our day together, I went online and ordered a ton of other items that I knew would suit me and hopefully fit me simply because I finally had some direction in my style and my understanding of what works for my body. Now I can shop literally anywhere (Target, Barneys, whatever) because I know what I'm looking for and that is literally half the battle. For me, working with Tiffany was like hiring a therapist for the day.

If you feel that you can't afford a stylist, go find one for free! Most department stores have stylists that will work with you to pull items the way that Tiffany does. You may not get quite the same level of service and attention, but it's way better than trying to do it all on your own. Tiffany recommends asking for the manager of the section you want to shop in (this worked really well for me when I was hunting for denim at Nordstrom!).

Explain to them what you are looking for, what your struggles are, and your goals. The manager should either be able to help you directly or find the best salesperson for the job! I also like to enlist the help of gals on the floor whose personal style I really like, or who maybe have a similar body shape. Bring a pinterest board of styles you like too! And if you feel like it's just not working with that person, walk away and try again another time, or move on to a different store.

On a personal note, I also wanted to talk about budget here a bit more. For me, at this point in my life, I'm going to for quality over quantity. I used to do the opposite because 1) I could get away with wearing a lot of different styles and shopping wasn't so hard, 2) I didn't have the budget and 3) I didn't care about longevity in my pieces, other than denim. That's all completely changed.

Now that it's harder to find pieces I love, when I do find them, I'm happy to invest in them. I feel like my body has settled into the size that it is, and I don't expect a huge fluctuation anytime soon, so I know that these items will suit me for a long time. Also, having higher quality pieces feels good to me: they are cut better, they will last longer, and I'd rather have a really great capsule wardrobe than a ton of throw-away pieces. I don't mind having a signature look or pieces that I go to over and over again, so I'm not worried about having tons of options.

That said... I also can't afford to shop like this all the time. I find it essential to invest in certain items - the ones that will get a lot of wear, and the ones that are show-stoppers - and fill in with other pieces that are a little more on-budget while still being on-brand.

I hope you guys are interested to see how this shopping experience carries over into my ongoing wardrobe update process, because my next post like this one is going to explore some fantastic budget finds, some great investment pieces, and a little more about how I'm applying everything I learned from shopping with Tiffany into growing my self-confidence and personal style. (Hint, hint, March's theme is going to be alllll about this!). And if you've got questions about this process, leave 'em below! I'd love to try and help answer anything I can!!