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Dates can be stressful. Especially first dates. Figuring out where to go, what to talk about, weighing whether it’s really worth meeting this stranger in the first place can take up a lot of mental energy. The last thing you want to be doing is spending hours picking out the perfect outfit for someone who could be your forever person OR someone who you smile and nod politely at for an hour while planning a graceful exit.
At 40, we’ve also been there done that enough to know that dinner and dressing up too much on a first date is neither necessary, nor advisable, especially when meeting someone from the apps. That first date is really a chemistry check, so you want to find the balance of expressing who you are, bringing your best self, and feeling comfortable.
Winter is my favorite time to outfit plan for a date. It’s colder so you can rock layers and feminine sweaters. I prefer to cover up and tend to lean a tad androgynous in my day-to-day style choices, but I love an excuse to dress a little more feminine and feel sexy, and cold weather seasons are the best seasons for style, offering the variety of skirts, tights, boots, and layering of patterns and textures.
This is why I have a few standby outfit combos on hand at all times that follow a number of unwritten rules:
- Are you comfortable? Always always always feel comfortable in your clothes on a date. If you don’t feel comfortable, you won’t enjoy yourself. And that’s the number one reason to be out in the first place. In general I try to avoid short skirts or extremely low cut tops. If this is your jam day to day. Then, please wear what you love and be yourself.
- Do you feel sexy? You don’t have to wear tight clothes to feel sexy. Find what is sexy to you and make that part of your fit choices. I personally love a lace moment or something feminine, paired with a more structured jacket and/or trouser.
- Do you feel like yourself? Wear something you would wear on a night out with friends. If you saw someone wearing what you were wearing, you would tell them you love it. You want to find someone who likes you for you, right? Then show them who you are.
- Where are you going? I’ll be honest, I feel like most of my go to date fits will work at most first date locations (dive bar, oyster bar, restaurant with bar, rooftop bar, coffee shop, even a nice restaurant), but if you are going to a nicer establishment, then skip the cute cardi/jeans combo and go for something a little more elevated: dress, blouse and trousers, etc. and add a trend piece and a heel. But I feel like these days, as long as you look put together and accessorize well, the eating or drinking location does not need to dictate the clothing pieces you choose.
- Does the outfit make you excited to go out? It’s so fun canceling plans, ammiright? I’ve been there. Days are long, the couch is so comfy, and there is endless content on Netflix. But that is comfortable. We know what a night in binging the newest HBO drama looks like. Dating, meeting someone new…the good time…that is less certain. Change is hard, but it can also bring variety and excitement, and maybe someone who will watch prestige TV with you – or, at least, a really good story. So, after you’ve dressed and accessorized, do you feel inspired to do a little shimmy in the mirror at yourself? Great. Go get ’em.
Check out some outfits below to inspire your next successful first date!
Lace Cami + Blazer
Consider for: Gallery Openings, and Nicer Bar and Restaurant dates
Blazer / Camisole / Pants / Bralette / Earrings / Necklace / Boots
This fit is crafted with intention and will give you options on your date. You want to wear a camisole that shows a little lace when you have the jacket on, and, importantly, one you feel comfortable wearing without the jacket, incase you get warm and/or feel like showing some more skin for whatever reason…
A challenge I often run into when wearing camisoles: what do I wear under a slinky lacy cami? The best solution I’ve found is a lace bralette that has tiny straps that can be somewhat concealed under the cami’s straps (or look like they are part of the cami). If you have a larger chest, you will need some support, and I’ve found a lacy bralette does the best job at being concealed under a thin camisole while also lying flat enough that you aren’t seeing the bulk of a, say, wired strapless bra break through the silk or satin.
Avoid racer backs or bandeau styles, unless you want the extra coverage. My favorite lace bralettes are from b.tempt’d. They are affordable and made by the same brand as Wacoal, so you know they give you great lift and coverage. And they’ve shockingly held up over the years. A satin bralette is also a great option, however it tends to not provide as much support.
Cardigan + Favorite Pair of Jeans
Consider for: Walking, Top Golf, Day, Coffee, Dive and Sports Bar dates
Cardigan / Jeans / Bag / Necklace / Ring / Shoes
I love this look for a more laid back date. It’s feminine while not feeling high maintenance. And the cardigan can be buttoned up or down depending on how flirty you are feeling. Red is always a great choice, as it’s a neutral primary color, and anyone can find a shade that works for their undertone. It’s also powerful, and that’s how you should feel on a first date. Add an easy ballet flat and some cutesy, fun jewelry to complete this pretty and put together first date look.
Sweater Dress
Consider for: Coffee, Museum, Nice Bar and Restaurant dates
Dress / Boots / Bag / Necklace/ Ring / Watch
I personally rarely wear dresses or skirts on first dates, but when I do, it’s a maxi or midi sweater dress. A sweater dress exudes elegance with minimal effort (my favorite kind of effort). The silhouette is streamlined by the clean lines, and you can dress it up or down, depending on the event. Also, it is so comfortable, so you will automatically feel good in it. I put this in the category of Cozy Sexy.
Boots are a must for a sweater dress. I like to keep the look clean with matching jewelry. While a tote would also look on point with this outfit, I am loving the slouchy clutch look. So sophisticated here in an off white by Mansur Gavriel. Also available in a larger size.
Stay tuned for more first date outfit recs!
