“I Let My Boyfriend Dress Me For A Work Week — Here’s What Happened”

by | Jul 26, 2017 | Style

By Alexandra Hanson

This. Is. Adorable.

I knew interning at Women’s Health would be fun, but I’d never have imagined I’d accept the challenge of letting my boyfriend choose my outfits for five working days! My goal: to see how someone who doesn’t have my dress insecurities would dress me. It would help me to come up with different style options for myself — and see how well my guy understood my particular style…

My Work Wardrobe

My winter wardrobe mainly consists of jerseys, like pullovers, boots and puff jackets, mostly in darker, simpler colours: black, olive green, burgundy and brown. I tend to enjoy layering, because it’s just way easier to toss off a layer when you get a little toasty. I’d say my style is very casual, but it does include an element of smartness.

READ MORE: We Challenged A Captonian To Wear Joburg Style For A Week

The Briefing

I could see the evil glint in my boyfriend’s eye when I told him about the challenge, and silently regretted suggesting it. I gave him three clear conditions, which he didn’t actually need to follow (but I secretly hoped he would). One: it’s cold outside, so please dress me at least semi-warmly. Two: I’m still interning, so I need to impress. And finally: I’m definitely not wearing the same outfit two days in a row to see if the team notice (yes, he did suggest that…).

With joking (hopefully) ideas of a “onsie look”, or “formal dress” days, I nervously left him to his own devices while my brain stewed over various comical outfit choices in another room. After what felt like ages and what sounded like frustrated grunts, I was called back to my room to inspect the damage. I mean… outfits. Laid out in five neat piles were surprisingly interesting combinations. To say I was pleasantly surprised was an understatement. But I couldn’t let him know how pleased I was with his choices. I wanted to let him sweat it out, so my response was: “Wait to read the written piece.”


Day 1: Monday

Day one’s outfit consisted of a green pullover, with a long-sleeve black shirt underneath, black jeans and my black heeled boots. Overall, the outfit is stylish, yet relaxed and casual… Although a scarf would have been appreciated on that cold morning.


Day 2: Tuesday

The second day’s outfit h­­ad me feeling more hopeful that my boyfriend had nailed my style. Blue skinny jeans paired with a black three-quarter-sleeved top and my favourite black heeled boots, the outfit has an edgy yet sophisticated look that even I hadn’t thought of putting together. Topping it off was my thick grey puff jacket, which kept the chill at bay, while adding a relaxed feel to the look.

READ MORE: “I Dressed Like My Boss For A Week — Here’s What Happened”

Day 3: Wednesday

Astonishingly, my boyfriend hadn’t seen any of my previous week’s work outfits. To my slight horror, he’d picked out the same top and boots I’d worn last Wednesday! I know two years and six months is a long-ish time to date someone, but the fact that we are so similar is a bit scary. This also just shows how attuned he is to my style, or perhaps we just have the same fashion feel. Today’s look involved my skinny blue jeans (again), paired with a burgundy undershirt and burgundy pullover top. His proud logic: if I get too hot at work, I can take the pullover off and still have the same colour on top!


Day 4: Thursday

Today’s look is a mix of smart and casual. For my top half he chose his favourite black pullover of mine with the wording “Je suis petite”. He absolutely loves this pullover because it says, simply, “I am little”, which he thinks I am. Because I had a blazer in my wardrobe, he just had to throw that in the mix for warmth and “to lift the look”. The bottom half: my skinny blue jeans (again…. I think he likes this pair) and white Nike sneakers – perhaps to show how “little” I am with my boots missing from the picture.

READ MORE: Classic Or Digital — What Your Wristwatch Says About You

Day 5: Friday

For the final day, I thought he’d go out with a bright bang! Luckily for me, he still kept the choices along the lines of what he feels is my style. Today’s look: my grey Woolies pullover, black jeggings (finally different bottoms!) and black boots. Plus, if I got cold, I could add my grey puffer to the mix. He even joined in on the fun, matching his outfit with mine.

The Verdict

To be honest, I don’t know if he has an excellent memory, or is just seriously attuned to my style, but he got it right. I’m a bit disappointed that he didn’t go bolder, but I’m glad that he still made me look fashionable for my internship. Overall, this challenge has taught me how aware my boyfriend is of my style and how much attention he pays to how I dress. I also now know that when he’s out shopping, there’s no excuse for him not coming back with a little something for me!­­

Here’s exactly how to spring clean your fitness gear. Plus: People on the internet are freaking out about this sneaker hack.

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