I bought Gap’s Sexy Boyfriend Jeans on sale a few months ago because I like “the boyfriend” silhouette, but did not want to invest heavily in the look. I’ve worn them frequently this Summer as a welcome roomy change to skinnies, straight legs, cut-off clamdiggers and even bootcuts jeans. They’ve worked out well. 

I have quite a high bagginess threshold so I sized up on the jeans to create a baggier fit on the waist, bottom and legs. This made the crotch point drop two or so inches below its usual position. These jeans fall right off with button and zipper fastened, and cannot be worn without a low slung belt. The droopy seat and back pocket positions would not meet with Team Back’s approval, but I bat for Team Front so I’m more tolerant of rear views that do not look tight and perky. These baggy jeans are not conventionally flattering, but they are on trend, extremely comfortable, and appeal to my tomboy streak. This makes them fun to wear and just flattering enough that I feel good in them.

I match these jeans with all sorts of soft blouses, knitwear, lace tops, blazers flats and bags, but like them best worn with a popped and scrunched masculine tucked in shirt, belt, clutch and low heels. No jewelry other than my watch, wedding ring and specs. The simplicity of the outfit really appeals to me, as does the marriage of timeless classics (shirt, pumps and belt) with on trend items (jeans and clutch). 

I won’t wear these jeans with an untucked top because the structure that is achieved by tucking and belting adds the polish that I strive to create in my outfits. I’m not a semi-tuck gal either, so it’s always full tuck and belt with boyfriend jeans for my style. I wish that the jeans were long enough to wear full length, but they are too short worn unrolled. So I’ll be wearing them rolled with booties, Converse sneakers and blazers in the early Autumn just so that I can wear them a little longer. 

I’ve been wearing clutch handbags during the day as I give my big bags a break. Surprisingly, I don’t find them impractical, and I’ve had no problem using one while I shop all day with a client. I have one hand free, or pop the clutch under my upper arm when I need to use both hands. I’m glad that the strategy works because I do love the look of a clutch. 

The powerful effect of classic wardrobe items was the the most important style lesson that I learned last year. This year, I’ve learned that I am happiest when my outfit contains at least one classic piece. That way it instantly feels simple, crisp and clean. We are always learning about our evolving styles and having fun along the way.

You are on Team Eye Shadow if you wear it daily or almost daily. You are on Team No Eye Shadow if you leave it off for at least half of the time. 

I have worn eye shadow once to a real life event. In true ’80s style, it was to my high school dance in 1987. My date after the dance couldn’t wait for me to take off the eye shadow as soon as we hit the after parties. Point taken and I couldn’t have agreed more with his assessment. 

Me and eye shadow are not friends because the effect, no matter how “natural”, looks too done up. This sounds crazy because I bat for Team Dressy but there you have it. I have a small face, but my eyes are relatively big, my lashes long, and my brows distinctive. As soon as I add eye shadow into the mix of mascara and eye brow pencil, I look and feel like a clown. Plus my eyes look too big for my face, and it just doesn’t work. I’ll stick to wearing mascara and eyebrow pencil daily, which adds just the right amount of polish to my style. I don’t change this eye make-up routine for formal events either. That said, if I was attending the Academy Awards, I’d probably wear a smokey eye. 

I am Team No Eye Shadow without a shadow of a doubt. 

Over to you. Are you on Team Eye Shadow or Team No Eye Shadow. Tell us why and no batting for both teams.

A peter pan collar is usually flat with rounded edges on the tips of the collar. They can be high, low and vary in width as seen in the examples below. You’ll find peter pan collars on blouses, shirts, knitwear, dresses, jackets and coats. They are classic so we see them every year. But every so often, classic looks become “on trend” so we’ll also see peter pan collars make fashion statements over the next few seasons. 

These collars get a mixed reaction from my clientele. Some adore the retro vibe, the softness of the rounded collars, their playful, romantic and arty integrity, and their feminine appeal. A pointy shirt collar is strict, crisp and masculine, whereas a peter pan collar creates a more ladylike and whimsical effect. Peter pan collars also do a great job of softening a very strong shoulder line. Some of my clients feel that they look more approachable and friendly in a peter pan collar. 

My other clients are dead set against peter pan collars because they look overly sweet, precious, girly and juvenile. Too much softness and not enough “grown-up authority”. 

I understand and agree with both points of view. The pointy shirt collar dominates my wardrobe because its strict, masculine integrity is precisely what appeals to me in the first place. But I also have a few peter pan collared pieces because I like their retro, feminine, soft and romantic vibe. There is room for both looks depending on my mood and what I want to communicate through my clothes on a given day.   

Do you wear peter pan collars, and do you prefer them to shirt collars? Or do you think peter pan collars are overly sweet, juvenile and precious. Can you look authoritative in a peter pan collar?

As Summer is slowly drawing to a close, we are gearing up for a new season of YLF Book Club. I’m excited! I’ve been reading up a storm and have discovered some true gems, tons of fashion fun that provides food for thought. That means lots of new titles we could chat about come Fall. But YLF Book Club is first and foremost about the movies and books you want to talk about. So of course we would love to hear your recommendations too. Don’t be shy and let us know if there is currently a title in YLF Books that you would like to discuss in depth. Have you come across a fascinating book you just have to share with us? Is there a style-related movie that intrigues you? A fashion documentary you feel everyone should know about? Tell us about it in the comments, and we might be chatting about it on the YLF forum very soon.

To refresh your memory, here’s the list of our previous Book Club titles.

New in YLF Books

In her first book, What I Wore: Four Seasons, One Closet, Endless Recipes for Personal Style, blogger Jessica Quirk of What I Wore wants to help readers create a versatile wardrobe with key pieces that will get maximum wear throughout the year. You will learn how to remix existing items, become a smarter shopper, put together wow-worthy ensembles for special occasions, and use affordable accessories to breathe new life into your basics and investment pieces. The book contains many fun colour illustrations based on Jessica’s own outfits, tips on how to budget for a four-season climate, tailoring tricks, storage and packing ideas, and suggestions for combining colours, patterns and textures.