We Asked The Men In Our Lives To Style Our Outfit For A Day—Here’s How They Turned Out

Your initial thought when you ask a man to choose an outfit for you is that (if he’s your husband or boyfriend) he may opt for something sultry like lingerie…or even your birthday suit. Hey, who can blame them? On the other hand, if it’s your dad or brother picking out your OOTD, he may choose something that resembles a burlap sack or your boxiest turtleneck in the dead of summer. That’s what we would’ve thought too, if we’re being totally honest. 

However, the results of this experiment showed us that, more often than not, men are paying attention and are much more in tune with what we like to wear (and what looks good on us) than what we give them credit for. Of course, there are some exceptions to this rule…but we’ll get to that. 

Out of fairness for the experiment, we told the guys what our plans were for the day – whether we were dressing for a date night, a picnic at the vineyard, or just to go run some errands. We asked them to pick out a complete outfit from head to toe (shoes and accessories included) without so much as a disapproving, or approving, glance from us. 

So without further ado, take a look at what happened when we asked the men in our lives to style our outfit for a day, and decide for yourself whether you’re impressed or your suspicions have been confirmed.  

Brittany Martinez

​​"So I actually felt extremely confident in my husband's styling abilities. I've never liked trying on clothes, but every time he has styled me, I get compliments, and I'd argue he has better taste than I do. I told him the rules and that there would be no cheating. 

Needless to say, I was not expecting to see these two outfits when he revealed what he'd chosen. One was an extremely cheap short skirt (I literally forgot I had a skirt that short) and another was a cheap dress.

I asked him, 'Out of everything in my closet, that's what you'd dress me in?'

His response: 'You hate it? I'm sorry. I feel like it would be cheating to just stick you in a nice dress'

Well, note to self, I need more basics. 

Anyways, he gave me a 'day look' and a 'night look.' The first look I told him was giving me ‘Saved by the Barbie’ vibes. For like a brunch. It's definitely something I'd never pick, but it did look a little better than I thought. I'd never wear high heels to meet up with girlfriends. I'll only wear them with him. Otherwise, I like to be comfy!

The second look was predictable, but I hadn't worn anything like it in a while. Tight pleather pants and a crop top? It's the kind of outfit he used to love picking for me when we lived in LA or Idaho. But since we've lived in more humid Miami, I mostly stick to dresses, skirts, and shorts. I did forget how much I liked a good pair of pants and boots though.

My closet is mostly full of dresses and hoodies so it's not like he had tons of options, but I would definitely trust him in a store."

Her husband's thoughts: "It’s extremely hard to make Brittany look bad. She looks good in everything, which is why I might be one of the only husbands I know who genuinely enjoys shopping for her. Ironically, she hates trying on clothes or shoes because she’s done it a million times over the years modeling and it feels like work. Dresses on her are my favorite - from minis to maxis to ball gowns. For this exercise, I avoided the obvious (looking at you, LoveShackFancy) and went for two looks that expressed her duality, at least in my eyes. Her favorite color is pink and she has a soft spot for Legally Blonde, so the daytime look has feminine, flirty, editor vibes with a cheeky nod to her love of sweaters. The second is inspired by her love of bombshell characters who are badass while embracing their femininity (Charlie’s Angels, Elena in Mask of Zorro, Lara Croft in Tomb Raider). Brittany’s a blackbelt in martial arts, so the night time look is a nod to the ninja inside of her while appreciating her sensuality."

Anna Hartman

“If I were assigning this task to any other man in my life, it’s safe to say that I’d be worried. However, my husband has been along for the ride on my fashion journey over the past 11 years – from an all-black, revealing wardrobe to Barbie-pink, then Parisian-inspired, and everything in between. He is also very much into fashion and is almost always with me when I go shopping, or at least I ask him his opinion if I’m browsing online. Oftentimes, he can spot where I’ve gone wrong even before I can, and he can tell if I’m losing touch with my personal aesthetic. He’ll call me out if I’m blindly following trends or trying something on that is overly revealing and doesn’t align with my values. He’s really good about letting me do my own thing, but also being honest with me about what looks best.” 

Her husband’s thoughts: “After 11 years together, I like to think that I know your style and what you like to wear. I’ve paid attention over the years. It’s also not hard to pick out something from your closet because everything is your style already. I know that you like soft colors and pink – but not too much pink. I chose this dress because it’s feminine, comfortable, and will be practical for going to the winery and sitting in the grass.”

Check out Anna's articles here.

Paula Gallagher

“My husband has a great appreciation of and a great eye for what’s beautiful, and he often has a better sense of style than I do, so I wasn’t too worried about asking him to pick out my outfit for the day. He did half-jokingly say he didn’t know what clothes I had and wanted me to model every item I owned for him so he could choose, but I left him to browse through the closet and my dresser on his own.”

Her husband’s thoughts: “Under immense pressure (due to my procrastination), I rushed into her closet in the morning and was quickly overwhelmed by the wealth of options. Green and gold/khaki are two of my favorite colors, and they look great on a blonde, blue-eyed girl, so these two pieces jumped out at me. The khaki wide-leg pants are new and a favorite of mine, and I wanted to find a shirt to go with them, something shapely and delicate for the summer. The green one with the white design went well (and yes, this shirt is actually green, even though my wife insists it is blue), and naturally she needed shoes to match. The white sneakers tied the outfit together nicely as they matched the white in the shirt. Comfortable and stylish (hopefully). Add the gold leaf earrings for a touch of Lothlorien, and I thought she looked smashing!” 

Check out Paula's articles here.

Gina Florio

“My husband chose a pair of skinny jeans with a backless short-sleeve top and black loafers. It's definitely a departure from my normal summer outfit of a comfortable sundress. He says he likes seeing me in jeans because he loves how my legs look in them, which is hilarious to me because I hate how my legs look in jeans! I haven't worn these loafers in almost two years and forgot I even had them in my closet, but he picked them because they matched the black in my shirt. It's not exactly the outfit I would choose for myself, but this was a fun experiment to find out what he likes to see on me!”

Check out Gina's articles here.

Stephanie Lavery

“I asked my husband to pick out an outfit for a casual dinner out with friends and kids. I was a little nervous, but he did a great job! I was impressed with his ability to accessorize.”

Her husband’s thoughts: “My inspiration was to keep the look Texas casual but add some cowgirl flair.”

Rachel Squier

“I love this outfit, it makes me feel like I'm a homestead queen with a bunch of goats and chickens, which is...the dream. I think my dad totally nailed my personal style. I was actually kind of shocked by how spot-on this outfit was! I guess he has been paying better attention than I thought!”

Her dad’s thoughts: “I picked this outfit because it’s country style and it’s a dress, and I like women in dresses because it shows their femininity, which is a good thing. Also, it's summery and you should be wearing dresses!”

Keelia Clarkson

"I'm happy to say I wasn't worried at all when my husband was assigned the task of putting together a full outfit for me. He has always had an eye for aesthetics and has a sense of style I trust. The process of him searching through my closet for the 'perfect' outfit was both fun and incredibly sweet to watch, as he took it really seriously. He also reminded me about some items I'd forgotten all about!"

Her husband’s thoughts: "I chose each piece of Keelia's ensemble to represent who she is and what I love about her. The A-line red dress is feminine and quiet but strong and passionate all at the same time. I paired the dress with a leather jacket and boot heels to bring a bit of classic edge to the look. A minimalist gold necklace and earrings added just enough sparkle without distracting. When brought together, this outfit captures a look that, to me, is very Keelia: feminine but strong, quiet with edge, stylish and timeless."

Check out Keelia's articles here.

Andrea Mew

"My husband actually has a pretty keen eye for style, so I knew he'd ace this assignment. He gave me a major confidence boost with the flirty, frilly blouse that contrasts beautifully with my mile-high heeled boots. I'm all legs and feel a bit like 1989 era T-Swift, so I can't complain!"

Her husband’s thoughts: "I tried to pick something that was dynamic and could be worn in a variety of settings: it’s modern and professional without being stodgy; alluring without being revealing; understated without being drab. I think with relatively minor tweaks, it could be seen simultaneously as alternative and traditional without delving wholly into one or the other. Obviously, I'm biased towards that particular necklace because it was something I gave as a gift. The necklace compliments the earrings, and together they all match the diamond ring on her finger (which I designed to reflect aspects of her personality)."

Check out Andrea's articles here.

Closing Thoughts

Did the men live up to your expectations? Would you let the man in your life choose your outfit for a day? While this may have been a silly, playful experiment to do with our husbands and dads, most of us can’t help but have an entirely new appreciation for how they pay attention to our style choices. Whether that’s by knowing which silhouettes or color palettes look good on us or by simply being aware of what we feel most confident in, it begs the question: have you been underestimating the man in your life too?

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